<?xml version="1.0" encoding="UTF-8"?><rss xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:content="http://purl.org/rss/1.0/modules/content/" xmlns:atom="http://www.w3.org/2005/Atom" version="2.0" xmlns:itunes="http://www.itunes.com/dtds/podcast-1.0.dtd" xmlns:googleplay="http://www.google.com/schemas/play-podcasts/1.0"><channel><title><![CDATA[Musings of a Mad Matt]]></title><description><![CDATA[Musings of a Mad Matt]]></description><link>https://musings.rightsized.tech</link><image><url>https://substackcdn.com/image/fetch/$s_!HU0C!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6f77b47d-c767-4274-b384-25bc1b7847d5_1280x1280.png</url><title>Musings of a Mad Matt</title><link>https://musings.rightsized.tech</link></image><generator>Substack</generator><lastBuildDate>Thu, 04 Jun 2026 00:18:48 GMT</lastBuildDate><atom:link href="https://musings.rightsized.tech/feed" rel="self" type="application/rss+xml"/><copyright><![CDATA[Matt Pieper]]></copyright><language><![CDATA[en]]></language><webMaster><![CDATA[mattpieper1@substack.com]]></webMaster><itunes:owner><itunes:email><![CDATA[mattpieper1@substack.com]]></itunes:email><itunes:name><![CDATA[Matt Pieper (Right Sized Tech)]]></itunes:name></itunes:owner><itunes:author><![CDATA[Matt Pieper (Right Sized Tech)]]></itunes:author><googleplay:owner><![CDATA[mattpieper1@substack.com]]></googleplay:owner><googleplay:email><![CDATA[mattpieper1@substack.com]]></googleplay:email><googleplay:author><![CDATA[Matt Pieper (Right Sized Tech)]]></googleplay:author><itunes:block><![CDATA[Yes]]></itunes:block><item><title><![CDATA[Salesforce Headless 360: What It Actually Means ]]></title><description><![CDATA[(And Why It&#8217;s Not New)]]></description><link>https://musings.rightsized.tech/p/salesforce-headless-360-what-it-actually</link><guid isPermaLink="false">https://musings.rightsized.tech/p/salesforce-headless-360-what-it-actually</guid><dc:creator><![CDATA[Matt Pieper (Right Sized Tech)]]></dc:creator><pubDate>Thu, 30 Apr 2026 18:29:30 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!HU0C!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6f77b47d-c767-4274-b384-25bc1b7847d5_1280x1280.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>The Internet is on fire across Reddit and LinkedIn with Salesforce&#8217;s recent announcement of Headless 360 at its TDX 2026 conference. While it&#8217;s certainly exciting to have an extendable range of APIs available to you to build off of the Salesforce platform, the concept of headless is nothing new.</p><p>As a matter of fact, Salesforce has flirted with Headless for years across Heroku, Commerce Cloud, and parts of Marketing Cloud. But just because you surface an API for a particular function&#8230;doesn&#8217;t mean that you&#8217;ve achieved a full Headless platform.</p><p>Headless requires the ability to replace the full User Interface that a company ships, in other words: you can build your own interface without much friction.</p><h2>Defining &#8220;Headless&#8221;</h2><p>To have a cogent discussion on this, we really need to define what headless means. Headless means we have a software architecture where the front-end (the head) is completely decoupled from the back-end logic and data storage (the body). What that means is we&#8217;re going to use a set of APIs to interact with the database, the business logic layer, and so forth to build our own UI.</p><div class="pullquote"><p>What a headless experience means is that you build your own User Interface (UI).</p></div><p>Headless, at its very basic definition, just means you can use a piece of software however you like, with whatever UI you want. A lot of headless software out there has its own webapp that you can log into, its own curated experience, but then you can extend it into your own.</p><h3>Examples in the Wild</h3><p>This has been long tail for omni-channel delivery. For instance, headless CMS (Content Mangement System). You have headless CMS vendors out there, and you&#8217;ve probably visited a website powered by them: example of theseare Contentful, Sanity, and to an extent Drupal. </p><p>From an OMS (Order Management System) driving e-commerce, you have your headless commerce examples such as Salesforce. Then you have Shopify, which is the shining headless commerce examle. </p><p>All headless means, at its very basic definition, is that you&#8217;re building a bunch of back-in connective tissue and your front end, allowing you to build that own experience.</p><h3>The Misconception: &#8220;No UI&#8221; vs. &#8220;Your UI&#8221;</h3><p>Headless, from an architecture standpoint means that, yes, you&#8217;re returning text in a backend API, but that doesn&#8217;t mean that it&#8217;s a backend text-driven user interface and experience. Every single webapp or mobile app that you use today receives text from the backend to the fronted to consume, and the frontend is sending text to the backend service(s).</p><p>What a headless experience means is that you build your own User Interface (UI).</p><div class="pullquote"><p>Even text is a user interface. </p></div><p>Don&#8217;t think of headless as, &#8220;Oh, well, headless isn&#8217;t for me because I&#8217;m just driving a text-based experience.&#8221; Think of headless as the ability to build your own experience for interacting with Salesforce.</p><p>Whether that is through a CLI experience, whether that is a ChatGPT or Claude experience, whether that&#8217;s an agent you&#8217;ve built, or you&#8217;ve built your own frontend web app to accommodate a different experience&#8230;that is the &#8220;head.&#8221; </p><p>Headless just means you can use the same APIs, the backend that other companies use in their frontend web apps, but with less opinionation. You&#8217;re not forced into a cookie-cutter experience that everyone else is using. </p><p>You can extend your own, whether that&#8217;s in a mobile app, a webapp, Slack app, or even a CLI if you&#8217;re feeling spunky.</p><div class="callout-block" data-callout="true"><p>Headless means we have a software architecture where the frontend (the head) is completely decoupled from the back-end logic and data storage (the body). What that means is we&#8217;re going to use a set of APIs to interact with the database, the business logic layer, and so forth to build our own UI.</p></div><h3>A History of Headless at Salesforce</h3><p>Salesforce has flirted with headless since Salesforce1 came out around 2013, driving a unified mobile experience, extended with Heroku, allowing you to connect your Postgres database directly to Salesforce. To have a first-class citizen postgres database that you could build your own application off of. </p><p>This took out the long latency API calls, created a syncable database, and allowed you to interact with your database in your webapp or mobile app without the increased latency and building your own wrappers and SDKs. You could use your preferred ORM to interact with your database and forget that you were building against Saelsforce. </p><p>While that wasn&#8217;t necessarily headless, directly, it was a long step towards it.</p><p>Then look at Commerce Cloud. Commerce has always needed to be headless. No matter what tool you&#8217;re using, you want to build your own commerce experience, and you need to have a headless platform to build those experiences, to interact with the platform, and essentially white-label it without knowing that you&#8217;re using a particular OMS or CMS even.</p><h3>Why Do We Need This? (The UI Problem)</h3><p>The number one complaint that Salesforce has is its not-so-great UI and UX. Tabs on tabs, lots of text, many ways to click around. Now, part of that is on Salesforce, and part of that is on us builders. A lot of builders haven&#8217;t leaned into Screen Flows to drive custom experiences, dynamic forms to surface info only when needed, or offloading fields from an object onto another to reduce complexity. </p><p>We do have the ability to create our own LWCs (Lightning Web Components) that, while not the best in the world, can greatly extend the UI and experience and customize it for your company&#8217;s needs&#8230;not the masses.</p><p>While the push for headlesss architecture is to extend AI capabilities, specifically Agetns, there&#8217;s a huge advantage for those companies who want to build their own interfaces.</p><p>For example, you can pare down Salesforce to have just a few screens in a modern webapp (or SPA) and give users the Web 2.0 experience that they&#8217;re used to. This is incredibly useful for cases such as external SDRs that you want to push into a specific function, or say for finance that doesn&#8217;t need to know all the ins and outs of Salesforce.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Enjoying what you&#8217;re reading? Subscribe to be notified of new posts.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><h3>The Technical Reality: Guardrails and Trade-offs</h3><p>When we think of headless and who can truly harness this, it&#8217;s not going to be every company. It&#8217;s going to be the companies that are relatively tech-advanced or relatively bleeding-edge who can build and maintain their own experience.</p><p>Now, most people, when they&#8217;re hearing headless, are thinking, &#8220;OK, cool, I can use generative AI and Claude or OpenAI and easily drive an experience for my reps, whether that&#8217;s to quickly create a record or to query data.&#8221;</p><p>We already have these tools in the MCP, but even within these environments, you&#8217;ll still need to put guardrails in place. </p><p>Think about all the guardrails we have in Salesforce&#8217;s UI today, these aren&#8217;t necessarily UI issues. These are data protection issues.</p><p>You&#8217;re still going to have your validation rules. You&#8217;re still going to have flows checking for the accuracy of content. You&#8217;re still going to have automations that take your input and send it elsewhere. You&#8217;re still going to have to build your own client side validations.</p><p>You&#8217;re still going to have to build on the Salesforce platform with Flow and Apex to extend it. At this point, there&#8217;s no standalone ability to drive automations unless you&#8217;re in that Salesforce UI.</p><p>The trade-off? Traditionally, that means more API calls. That&#8217;s going to be against your API call usage. That headless experience is the same as integrating with Salesforce. You&#8217;re just using a different set of APIs that are better suited to these experiences.</p><h3>The Path Forward</h3><p>It&#8217;s clear that Salesforce is setting up their architecture to build revenue generating features for themselves in the future&#8230;predominately linking Salesforce and Slack together. This launch gives them a twofold advantage: ability to cater to customer demands but predominately to build their own Slack revenue features.</p><p>For customers you can embed these new experiences, say, within your ERP to take an action from a finance standpoint, but none of this is really new. We&#8217;ve had these abilities to do it. We&#8217;re just receiving better tooling with more guidance and a push from the Salesforce marketing teams.</p><p>Headless is exciting. It always has been, as a backend engineer myself, this is the world we live in. But for many builders on the Salesforce platform it&#8217;s a different way of thinking, and your builders and them people on your team aren&#8217;t likely to be able to take full advantage of them (yet). </p><p>Be very careful with this tooling. Talk with folks who understand this space, who have built these things, who are perphas engineers, and have built outside of Salesforce and used headless apps elsewhere.</p><p>There&#8217;s a lot of misinformation out there and listening to it can send you into a world of hurt.</p><p>That&#8217;s why Right Sized Tech exists, to blend product engineering experience with standard GTM abilities to take advantage of these features. To show you the possible, to build out proof of concepts to extend your platforms across other channels and verticals. We&#8217;ve built these experiences before without Salesforce&#8217;s headless APIs, and we&#8217;re excited to leverage the new endpoints to build something even greater.</p><p>So that being said, what are you excited to build?</p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/p/salesforce-headless-360-what-it-actually?utm_source=substack&utm_medium=email&utm_content=share&action=share&quot;,&quot;text&quot;:&quot;Share&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://musings.rightsized.tech/p/salesforce-headless-360-what-it-actually?utm_source=substack&utm_medium=email&utm_content=share&action=share"><span>Share</span></a></p>]]></content:encoded></item><item><title><![CDATA[The 2026 AI Hangover]]></title><description><![CDATA[Why Rushing is the New Technical Debt]]></description><link>https://musings.rightsized.tech/p/the-2026-ai-hangover</link><guid isPermaLink="false">https://musings.rightsized.tech/p/the-2026-ai-hangover</guid><dc:creator><![CDATA[Matt Pieper (Right Sized Tech)]]></dc:creator><pubDate>Fri, 09 Jan 2026 18:24:10 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!HU0C!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6f77b47d-c767-4274-b384-25bc1b7847d5_1280x1280.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>It&#8217;s the first week of 2026. Like every other leader right now, you&#8217;re probably looking at your dashboard and asking: <em>&#8220;Am I behind on AI? How do I catch up?&#8221;</em></p><p>Here&#8217;s the truth: nobody is really &#8220;ahead&#8221; yet. We aren&#8217;t even in the second iteration of this tech (generative AI). But with over <strong>70% of AI projects failing to deliver an ROI</strong>, the real question isn&#8217;t how fast you can move; it&#8217;s where you&#8217;re placing your bets.</p><p>Most orgs are throwing money at AI tooling based on &#8220;hopes and dreams.&#8221; Others are investing just to say they did, knowing they&#8217;ll get zero results but hoping for a &#8220;learning experience.&#8221; Then there&#8217;s the majority: sitting on the sidelines, waiting to see if the dust settles, or worse, stuck in analysis paralysis.</p><p><strong>Waiting is a mistake.</strong> AI isn&#8217;t going away. Whether it delivers AGI or just becomes a more efficient power tool next to us doesn&#8217;t matter. What matters is that you stop treating it like a novelty toy and start treating it like a business fundamental.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption"><strong>Before we dive in:</strong> If you find this perspective valuable, consider subscribing to <em>Right-Sized Musings</em> for no-nonsense takes on tech strategy.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><h2>The &#8220;Kindling&#8221; Behind the Fire</h2><p>We have a massive problem in tech culture: we ship MVPs (Minimum Viable Products) or POCs (Proof of Concepts), declare them a success, and then never go back to harden them. We &#8220;operationalize&#8221; them without actually <em>operationalizing</em> them.</p><p>AI is about to perpetuate that at an exponential pace. We&#8217;re developing &#8220;AI ADHD,&#8221; hopping from one fire to the next because the tech makes it easy to bang out a solution. But look behind you: there&#8217;s a massive pile of kindling in the form of technical debt, disconnected platforms, and processes that just don&#8217;t jive.</p><blockquote><p><strong>&#8220;If you don&#8217;t iterate based on real feedback, you&#8217;re not building an MVP; you&#8217;ve built your final product. Sometimes we need to be honest about that rather than hope we&#8217;ll return to harden our first attempt.&#8221;</strong></p></blockquote><p>The winners in 2026 won&#8217;t be the ones with the most agents; they&#8217;ll be the ones who realize that a POC is just a hypothesis. It&#8217;s a first attempt. In the scientific method, you have a control and variables. Your MVP is designed to test that hypothesis and refine your build. If you don&#8217;t iterate, you&#8217;ve just shipped your legacy code on day one.</p><h2>Back to the Basics: The Magical Triangle</h2><p>Regardless of your AI roadmap, you need to look at the &#8220;magical triangle&#8221; of <strong>People, Process, and Technology.</strong> The reality is that the more things change, the more they stay the same. High impact vs low effort, stakeholder alignment; these rules still apply. We&#8217;ve just spent years pushing them aside because it&#8217;s easier to buy a tool than to do the &#8220;grunt work&#8221; of talking to humans and building alignment.</p><h3>1. Technology: Stop the Bloat</h3><p>Before you add an &#8220;AI layer,&#8221; look at your underlying stack. Most orgs view tech through a cost-cutting lens; removing seats or making blanket calls like, <em>&#8220;I don&#8217;t know why Marketing uses that tool instead of ours.&#8221;</em> Stop guessing. Ask <em>why</em> they use it. Where&#8217;s the overlap?</p><blockquote><p><strong>Follow the 80/20 rule: If you&#8217;re paying for a platform but only using 10% of the features, and it&#8217;s not delivering outsized value, cut the footprint now so your AI doesn&#8217;t have to navigate a digital junkyard later.</strong></p></blockquote><h3>2. Process: Capturing &#8220;Unwritten Logic&#8221;</h3><p>This is the biggest lever you have. You need to document your critical workflows in detail. I&#8217;ve sat in rooms where we locked Operations, Product, and Engineering together and had Ops walk through their actual day-to-day.</p><p>I watched engineers who swore, &#8220;That&#8217;s not how it works,&#8221; eat their hats in real time. They had no idea how much time was wasted on manual workarounds. Instantly, they came up with solutions that reprioritized the entire roadmap.</p><p>When you do these process interviews, two things happen:</p><ol><li><p><strong>You realize half the bottlenecks don&#8217;t even need an &#8220;agent.&#8221;</strong> They just need a better workflow.</p></li><li><p><strong>You build the documentation that becomes the &#8220;brain&#8221; for your future agents.</strong></p></li></ol><p>Our people use <strong>&#8220;unwritten logic,&#8221; </strong>tribal knowledge, quick Slacks, and those &#8220;gut moments&#8221; that agents don&#8217;t know how to do unless we program them in. Without this documentation, agentic implementations fail every time because the agent expects one thing, while the day-to-day reality is something else entirely.</p><h3>3. People: Expanding the Pie</h3><p>We need to move away from &#8220;AI replaces people&#8221; and toward &#8220;AI empowers people.&#8221; You have to give your team a safe space to learn.</p><p>Don&#8217;t just turn ChatGPT or Gemini on for every employee and get frustrated when they don&#8217;t use it. We&#8217;ve seen this movie before with Salesforce, email, and Excel; we train them once and never talk about it again.</p><blockquote><p><strong>&#8220;Expand the pie with AI. Increase revenue and decrease non-personnel expenses; instead of just trying to cut the headcount to drive a bottom line.&#8221;</strong></p></blockquote><p>The reality? Most employees today still struggle with right-clicking a mouse or writing an Excel formula. You cannot expect them to navigate complex, language-specific AI software without guidance. Share best practices. Leverage their skills.</p><h2>Use AI to Get Ready for AI</h2><p>You don&#8217;t have to reinvent the wheel. Use the tools you have to prepare for the future tooling you want.</p><p>Start recording your process interviews on Zoom or Google Meet. Use Gemini to transform those transcriptions into actual documentation. That&#8217;s a proper way to use AI <em>today</em> to be ready for the agents of <em>tomorrow</em>.</p><p>We shouldn&#8217;t insist that our employees learn on their own or after hours. We should instead carve out time in our day-to-day to assist, to drive conversations so that folks know they&#8217;re not alone in their journey, to share best practices, and to drive innovation.</p><h2>The Bottom Line</h2><p>Don&#8217;t try to keep up with the Joneses. Be your company. Remember the secret sauce that got you here. Don&#8217;t pull resources from the &#8220;fires&#8221; that are actually working just to chase hype driven by FUD or FOMO.</p><blockquote><p><strong>&#8220;The code was never the hard part. The hard part is education, understanding, alignment, and prioritization. AI can accelerate what we do, but it can&#8217;t fix a broken business model.&#8221;</strong></p></blockquote><p>Do the grunt work. Harden your prototypes. And for everyone&#8217;s sake, stop rushing.</p><h3>Let&#8217;s Move the Needle</h3><p><strong>Enjoyed this?</strong> Here are three ways to keep the conversation going:</p><ol><li><p><strong>Leave a comment:</strong> What &#8220;unwritten logic&#8221; is currently keeping your team afloat?</p><p></p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/p/the-2026-ai-hangover/comments&quot;,&quot;text&quot;:&quot;Leave a comment&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://musings.rightsized.tech/p/the-2026-ai-hangover/comments"><span>Leave a comment</span></a></p></li><li><p><strong>Share this post:</strong> Send it to a leader who is currently drowning in AI hype.</p><p></p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/p/the-2026-ai-hangover?utm_source=substack&utm_medium=email&utm_content=share&action=share&quot;,&quot;text&quot;:&quot;Share&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://musings.rightsized.tech/p/the-2026-ai-hangover?utm_source=substack&utm_medium=email&utm_content=share&action=share"><span>Share</span></a></p></li><li><p><strong>Audit your stack:</strong> If you need help hardening your &#8220;Magical Triangle,&#8221; let&#8217;s talk. </p><p></p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://www.rightsized.tech&quot;,&quot;text&quot;:&quot;Let's Talk&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://www.rightsized.tech"><span>Let's Talk</span></a></p></li></ol><p></p>]]></content:encoded></item><item><title><![CDATA[You See, I Was Never Supposed to Be in Tech]]></title><description><![CDATA[A personal journey intertwined with a technology vendor and the divergent paths taken.]]></description><link>https://musings.rightsized.tech/p/you-see-i-was-never-supposed-to-be</link><guid isPermaLink="false">https://musings.rightsized.tech/p/you-see-i-was-never-supposed-to-be</guid><dc:creator><![CDATA[Matt Pieper (Right Sized Tech)]]></dc:creator><pubDate>Wed, 08 Oct 2025 13:45:04 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/2bde0d61-8429-4b7b-bde0-e2ac4954f33c_2700x2160.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Today I sit in my backyard, MacBook Pro in my lap, browsing the sessions available at Dreamforce. This year, I have the luxury of having time to review sessions and build a more coherent strategy than in years past. Having gone through another round of layoffs, I've had time to reflect on my career, and as a result, Salesforce has been a significant part of it.</p><p>My Salesforce story, like many of yours, came from a rather interesting angle. Since I can remember, I've used a computer. My first computer was an Acer 286. I remember lightning traveling through our phone lines and wiping out our computer, and my father deciding he was done with proprietary tech and would start building our own bare metal machines.</p><p>I remember Windows 3.1, I remember installing Windows 95, and being blown away by Weezer's Buddy Holly at launch. I started coding in MS-DOS, editing bat files to resolve driver conflicts or to free up memory. I remember opening a new game at Christmas and being excited about the challenge of getting it to launch more than playing it itself.</p><p>In high school, I took independent study lessons in C++ and, with one of my best friends, built the school's attendance system. But I never wanted to be a software engineer (I wanted to be a studio audio engineer). The problem? The industry was trending downward, college programs were highly competitive, and it was an impossible industry to break into from Louisville, Kentucky.</p><p>September 11, 2001, happened, which drew me to enlist in the US Army, deferring my college plans. After balancing full-time work and completing my undergraduate degree, I pursued a Career in Finance and Economics instead of engineering. </p><p>You see, I never wanted to be in tech. </p><p>I still wanted to code and be interested in tech, but I didn&#8217;t want to do it full-time. I wanted to delve into economic theory and conduct research, study econometrics, and pursue a PhD. The problem was I wasn't <em><strong>that</strong></em> good at math.</p><p>When I left the Army, it wasn't a great time in the economy, and finance roles were challenging to get, so I took a job as a software engineer. Then I got my MBA from Ohio State, determined to finally break into finance through venture capital.</p><h2>The Day Everything Changed</h2><p>But then I got a job in venture capital, and I was excited to go out and learn about startups and help them scale. But my first day on the job, they told me, "Hey! You used to be an engineer, here's Salesforce."</p><p>"What the f*** is Salesforce?" I said.</p><p>They had implemented it as a carbon copy of a partner firm's org, with changes made here and there. It was a square peg in a round hole. The data model was flawed for the business; there was no training, and no clear vision. That's where I came in.</p><p>And that's when I discovered something surprising.</p><p>Salesforce wasn't just software; it was a platform where you could build things. Real things. I learned about the business and its goals, worked with the boss, a successful entrepreneur who had an exit, to apply the Socratic method, and learn how to ask the right questions. </p><p>We built an entire instance and reimplemented it, connecting Salesforce to Microsoft SQL Server to drive SSRS reports, and later connected to Tableau when it first emerged onto the scene.</p><p>I was pulled in multiple directions, from administering Salesforce to migrating our on-prem servers to Office 365, to implementing a new ERP, to rebuilding the entire networking infrastructure in that role. All while advising early-stage startups on their strategy.</p><p>I remember partnering with companies like AWS to integrate their services into our portfolio. I remember working with Lyft to introduce them to the Columbus market and make connections.</p><p>I was immersed in Apex and Eclipse while helping to write Ruby for the startups I was involved with. I remember Heroku launching, I remember being excited that when Salesforce1 came out, I could connect my Rails app directly to a Postgres database with Salesforce. I could build entire interfaces and applications that could update and read from Salesforce in an MVC context. My mind was blown.</p><p>This wasn't just a CRM. This was a community of builders, all figuring it out together. There were forums where people shared code snippets, conferences where the company's founders would sit down and talk with customers like equals, and a genuine sense that we were all building the future together. I noticed parallels between traditional development communities and this emerging SaaS one.</p><p>I was never supposed to be in tech, but the community lured me away from my economics dream.</p><h2>Growing Up Together</h2><p>Over the next decade, both Salesforce and I evolved in parallel ways.</p><p>I went from that first accidental role to leading teams of Salesforce professionals, IT professionals, and product engineers, teaching them about how each other worked. I rescued orgs, integrated acquisitions, and touched hundreds of orgs through my consulting travels. </p><p>I implemented Service Cloud, Sales Cloud, CPQ, Billing, Pardot, Mulesoft, and Tableau; you name it. I spoke at conferences, podcasts, and webinars, and met amazing people I never would have encountered otherwise.</p><p>Meanwhile, Salesforce evolved from that scrappy middle-market company into the enterprise giant it is today. They acquired companies, expanded into every corner of the business software market, and became the undisputed leader in CRM. Their Dreamforce conference grew from a few thousand attendees to over 170,000.</p><p>We were both becoming more sophisticated, more polished, more professional. And there was nothing wrong with that evolution. It was necessary, even admirable.</p><p>But something was happening to both of us along the way.</p><p>I was never supposed to be in tech, but I found myself leading a team that took a company public. I had stepped away from Salesforce for a minute to lead a team of Workday and NetSuite professionals, and picked up a scrappy IT team along the way.</p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://musings.rightsized.tech/subscribe?"><span>Subscribe now</span></a></p><h2>When the Party Changed</h2><p>I look back at all the Dreamforces I went to before the pandemic and then the ones after with a bit of sadness.</p><p>Dreamforce used to be a party and a celebration. A wink and a nod that we all knew it was a sales and marketing event, but we knew that the community had tons of sessions that weren't designed to sell but to educate. Salesforce always had its major product launches, but they were woven subtly into the experience.</p><p>I remember seeing people stand in line for hours to get a stuffed animal from a keynote session. I remember having to book a ticket to Dreamforce within an hour of launch. My friends and I had text chains, a coworker ran down the hall to pull people out of meetings. Because we knew our favorite hotel would sell out within an hour.</p><p>I remember late-night conversations in hotel lobbies where strangers would become collaborators, where someone would sketch out a solution to your problem on a napkin, where the Salesforce employees felt like fellow travelers rather than corporate representatives.</p><p>The conference sprawled across downtown San Francisco: the Palace, the Hilton Union Square, the AMC next to Moscone, plus Moscone and a sprawl across the Marriott. Every corner of the city buzzed with Trailblazers wearing their lanyards like badges of honor*</p><p>After the pandemic, we saw Dreamforce shrink to just Moscone and Marriott. That greatly reduced the footprint and the number of sessions, so new product launches felt in your face. We saw this with Genie, then with Agentforce. The community sessions got squeezed out to make room for sales pitches.</p><p>Today, there are still tickets available to Dreamforce. That sentence would have been impossible to write five years ago. We dropped from 170k attendees to 45k, the buzz was gone.</p><p>You see, I was never supposed to be in tech, but at this point, I found myself as a commercial leader in startups. Managing a product team, but also the internal tooling across Salesforce, ERPs, HRIS, and billing. Somehow, I was a tech leader, yet also mired in the day-to-day operations of numerous other business processes.</p><h2>What We've Both Become</h2><p>I look at who I've become, and I'm proud of the journey. I've evolved from an introvert who stumbled into Salesforce to someone who can engage with anyone, walk into any organization, and help them transform their business. I've built a reputation, a network, a career I never expected.</p><p>Salesforce has grown too, into a platform that can handle the most complex enterprise workloads, that can integrate with anything, and that can scale to serve millions of users. They've become the backbone of modern business.</p><p>But we've both lost something in the process.</p><p>I've become polished, professional, strategic. I can give a presentation to C-suite executives and hold my own in any boardroom. But do I still have that sense of wonder I felt when I first connected a Rails app to Salesforce? Do I still get excited about the pure possibility of building something new?</p><p>Salesforce has become enterprise-focused, acquisition-heavy, and AI-obsessed. They can serve any Fortune 500 company and handle a wide range of use cases. But do they still remember what it felt like to be the scrappy underdog empowering small businesses and accidental admins?</p><p>I witnessed that loss of community in the Salesforce ecosystem. I watched as executives cared more about growing the bottom line and pleasing the analysts of The Street than their customers. I watched as a company that used to take a stand slipped into the shadows.</p><p>We've both been incredibly successful. But success has a way of changing you, sometimes in ways you don't notice until you look back.</p><p>You see, I was never supposed to be in tech, but it&#8217;s the path that has shaped me, perhaps as much as the army did.</p><h2>The Next Generation</h2><p>Here's what keeps me up at night: How will the next Matt Pieper find their way into this world?</p><p>When I stumbled into Salesforce, it was a platform where you could quickly build something meaningful, where the community welcomed newcomers, and where you could go from zero to hero in a matter of months. The barrier to entry was low, the community was supportive, and the company felt accessible.</p><p>Today's Salesforce ecosystem is undeniably more powerful, but it's also more complex, more corporate, more intimidating. The conferences are slicker but less intimate (yup, it was intimate at 170k people!). The platform is more capable, but it is also harder to learn. The community is larger but more fragmented. </p><p>The days of the solo admin should be over with such a large platform, but they are still prevalent. We should have defined ownership at this point, but we still watch as teams fight over who is responsible for the platform.</p><p>Will the next accidental techie, the next person who never planned to be in this industry, find the same sense of possibility and community that drew me in? Or will they encounter a mature, polished, enterprise-focused ecosystem that's forgotten how to be scrappy?</p><p>I have no regrets about my journey or Salesforce's evolution. We both had to grow up. But I wonder if, in becoming everything to everyone, we've lost something essential about what made us special in the first place.</p><p>You see, I was never supposed to be in tech. But maybe that's exactly why I belonged here; at least, in the version of here that used to exist. The version that welcomed accidental travelers and celebrated the joy of building something from nothing.</p><p>The question now is whether there's still room for people like that old version of me in the new version of this world we've built together.</p><p>Years later, I'd attend TDX and have the closest seats to Weezer that I've ever had. But sometimes I wonder if that teenage version of me, the one who got excited about installing Windows 95, would recognize the person I've become, or the industry I've helped create.</p><p>You see, I was never supposed to be in tech, but being in tech has now led me to become an entrepreneur all these years later. Now applying all those principles I learned from advising startups to my own business - a lifestyle business that I&#8217;m more than happy to have: Right Sized Tech.</p><p>What has your journey been? Where will it take you next?</p><div class="captioned-button-wrap" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/p/you-see-i-was-never-supposed-to-be?utm_source=substack&utm_medium=email&utm_content=share&action=share&quot;,&quot;text&quot;:&quot;Share&quot;}" data-component-name="CaptionedButtonToDOM"><div class="preamble"><p class="cta-caption">Think someone would find this interesting? Share away!</p></div><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/p/you-see-i-was-never-supposed-to-be?utm_source=substack&utm_medium=email&utm_content=share&action=share&quot;,&quot;text&quot;:&quot;Share&quot;}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://musings.rightsized.tech/p/you-see-i-was-never-supposed-to-be?utm_source=substack&utm_medium=email&utm_content=share&action=share"><span>Share</span></a></p></div><div><hr></div><p>*Well, not me, as a street photographer, I travel incognito. If I look like I&#8217;m a conference attendee, I&#8217;ve done something wrong.</p>]]></content:encoded></item><item><title><![CDATA[Why AI Needs To Be Enterprise Wide]]></title><description><![CDATA[Not A Point to Point Solution. Why each platform-specific agent that you build is building another silo and preventing you from realizing economies of scale.]]></description><link>https://musings.rightsized.tech/p/why-ai-needs-to-be-enterprise-wide</link><guid isPermaLink="false">https://musings.rightsized.tech/p/why-ai-needs-to-be-enterprise-wide</guid><dc:creator><![CDATA[Matt Pieper (Right Sized Tech)]]></dc:creator><pubDate>Mon, 06 Oct 2025 15:01:06 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/2f9ba327-7df1-4472-a56c-96877e299100_2160x3240.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Here&#8217;s the problem: when you build AI solutions on a platform-by-platform basis, you&#8217;re creating silos and proving Conway&#8217;s Law in the AI era. Siloed teams using siloed platforms create siloed applications, and that inefficiency scales at the speed of automation. </p><p>Simply put, when your teams aren&#8217;t communicating effectively, you end up building solutions that satisfy the requirements of one team but not the company as a whole.</p><p>What you end up with is RevOps building agents in Salesforce, Finance building them in NetSuite, and Engineering building them in their own stack, with nobody able to communicate with each other or reuse any components.</p><p><strong>Think about what </strong><em><strong>should</strong></em><strong> be possible:</strong> RevOps publishes tools that Engineering can pull from to show subscription and invoicing information in-platform. Finance creates data models that Sales can leverage for forecasting. Operations builds workflow components that every department can plug into their processes.</p><p>This isn&#8217;t science fiction; it&#8217;s basic modular architecture applied to AI tooling. But it only works if everyone&#8217;s working from the same sheet of music.</p><blockquote><p><strong>The Platform Principle for AI:</strong> Having teams on the same platform allows you to have a cohesive, unified, understandable framework that teams can use to speak to each other. This is what reduces bottlenecks and drives efficiency. Not AI itself, because AI without people and process improvements and management just repeats the same mistakes we&#8217;ve made over the last 20 years with SaaS: just at a greater and faster scale.</p></blockquote><h2>The Vendor Landscape Is Fighting Yesterday&#8217;s War</h2><p>Currently, we&#8217;re witnessing the gap between AI hype and reality play out across vendors. Some are approaching this with measured realism, preparing their boards for a different future in earnings, willing to jettison products when it makes sense. Others are doubling down on walled gardens, trying to make their slice of the pie bigger rather than expanding the pie itself.</p><div class="pullquote"><p>This is blue ocean strategy at play - create an uncontested market space rather than competing in existing markets.</p></div><p>The winners in this environment realize that when you&#8217;re in massive change, you don&#8217;t quibble with competitors&#8212;you focus on strategy and product. You don&#8217;t hold onto sacred cows that must remain in place.</p><h3>Salesforce&#8217;s Walled Garden Problem</h3><p>This is why I think Salesforce&#8217;s AI strategy is ultimately flawed. We all know Salesforce has wanted to be a data company for the last two decades. After all, it&#8217;s why we have the phrase &#8220;if it&#8217;s not in Salesforce, it doesn&#8217;t exist.&#8221; It&#8217;s why we have so many vendors push data into Salesforce: call recording, notes, everything. It&#8217;s why we saw the experiments with data.com and later the acquisitions of MuleSoft and Informatica.</p><p>But think about the fundamental absurdity here: <strong>why are we storing files in Salesforce when it&#8217;s the most expensive storage rather than S3 or OneDrive or Google Drive? Why are we not using the best tools for the job that can be used ubiquitously across the enterprise?</strong></p><p>Salesforce has pushed Data Cloud with mild adoption rates when we&#8217;ve been shoving data into our data warehouses for years&#8212;the same warehouses that already have our data, have pipelines between our SaaS sources (HRIS, ERP, CRM, OMS) plus our core domain product data if you&#8217;re a product company.</p><p>We see Agentforce&#8217;s abilities grow and mature, but it only works inside Salesforce. What if we want to build agents in Finance? In Operations?</p><p><strong>The Salesforce AI strategy today:</strong></p><ul><li><p>Charging customers to ingest data they already have in their warehouses</p></li><li><p>Building agentic flows that don&#8217;t extend outward easily</p></li><li><p>No application layer to build better apps</p></li><li><p>Customers are still complaining about the UI with no alternatives</p></li></ul><p>As SaaS platforms start to decrease in importance and become more of the database layer, how do these walled garden strategies play out? We see Salesforce&#8217;s CEO, Marc Benioff, constantly belittling other companies' strategies while ignoring that his community is turning against him. He quibbles with ServiceNow and tries to create a service business. We see agentic products bolted onto Salesforce offerings.</p><p>Here&#8217;s what&#8217;s wild: Salesforce has the most unique positioning with a third-party connector, MuleSoft Composer. You&#8217;d think they could use this positioning to make Composer the agentic competitor to Zapier and Workato, allowing them to diversify their strategy. They&#8217;re investing heavily in Slack, but once again, this feels like a disconnected experience when the Salesforce umbrella has so many products underneath it.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption"><strong>Enjoy what you&#8217;re reading? </strong>Subscribe to get insights like this in your inbox. </p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><h3>The Microsoft and ServiceNow Gambit</h3><p>Contrast this with Microsoft. While they stumbled out of the gate with Copilot in the enterprise, they&#8217;re doing a decent job with Power Apps and their GitHub products. They&#8217;ve also signaled that they&#8217;re jettisoning their CRM products.</p><p>ServiceNow is entering the CRM space, which is interesting. Why would they invest the time and energy to enter this crowded market (Oracle, Salesforce, HubSpot, Microsoft)? </p><p>All this indicates that companies are realizing they need to own everything in order to stay relevant, so they&#8217;re straying from their core competencies. But they&#8217;re all sluggish.</p><p>The weakness with Microsoft is that it relies heavily on its partnership with OpenAI rather than building its own technology like Google. OpenAI pulling the rug from under them as they enter into competing territory to make money could be devastating, and I think Satya Nadella knows it.</p><p>Neither Microsoft&#8217;s (Copilot) nor Google&#8217;s (Gemini) productivity AI tooling is wowing users, but I think that will change in the coming years. It&#8217;ll be interesting to see how Google approaches the next steps with AppSheet as their answer to Power Apps, and it&#8217;s not very good.</p><h2>The Third-Party Orchestration Layer Opportunity</h2><p>CTOs and CFOs don&#8217;t want duplicative spend. Whoever can solve this wins. <strong>CFOs don&#8217;t want to buy cutesy names in 2025; they want to buy value.</strong></p><p>We saw companies advertise to business teams in Marketing and Sales over the last 15 years. The new focus will be on cost-conscious finance teams that are facing continued pressure from their boards to grow margins, especially in a cash crunched capital market.</p><p>This is where third-party AI orchestration layers stand poised and ready to connect applications and experiences. Platforms like n8n, Make, Workato, Zapier, and Retool are completely agnostic of the platforms they interact with and can adapt as individual apps are replaced.</p><p><strong>What this enables:</strong></p><ul><li><p>Buy once, cry once; reducing overall maintenance costs</p></li><li><p>Increased ramp speed as the company works across the same sheet of music</p></li><li><p>Stitch processes together while using the AI capabilities of their own platforms</p></li><li><p>Reusable components across departments and teams</p></li></ul><p>SMBs and mid-market companies have an opportunity to be more agile here. Using AI-centric ERPs like Rillet, combined with a multitude of CRMs or service platforms. They can utilize AI-centric dialers and note-taking apps, leveraging AI orchestration layers to integrate these applications.</p><p>However, we also see Microsoft poised to play a major role itself. They&#8217;ve spent decades in the enterprise space, and while they don&#8217;t have the sexiest products, they do become easier to use with AI. Power Apps connects to a wealth of information across OneDrive, Email, Teams, and SharePoint. While this isn&#8217;t sexy to the average SMB, this is immensely powerful in full Microsoft shops, especially when you layer in access to Azure and core infrastructure often running in these orgs.</p><blockquote><p><strong>The key question:</strong> Will we see third-party startups that are agnostic ramp up because of agility? Or are they priced out? That remains to be seen.</p></blockquote><h2>What You Should Actually Do</h2><p>As you evaluate your AI platform in your organization, it&#8217;s important to realize that you can experiment now with various platforms at a small scale. But it&#8217;s far more important to start organizing your data in such a way that you can use it in any agentic platform.</p><p><strong>Your AI readiness checklist:</strong></p><ul><li><p>Start documenting all the institutional knowledge that&#8217;s in folks&#8217; heads (your AI strategy cannot tap into undocumented knowledge)</p></li><li><p>Get your employees comfortable with AI strategies and techniques</p></li><li><p>Provide stepping stones, not ultimatums</p></li><li><p>Organize your data to be platform-agnostic</p></li><li><p>Choose one or two enterprise-wide agentic platforms, not one per SaaS tool</p></li></ul><p>Don&#8217;t thrust AI upon your teams. Provide stepping stones to help them become comfortable. Because then they&#8217;ll start to understand it better and how it can apply to them every single day. Encourage your teams not to generate slop but to use their brains and let AI augment it.</p><p>If you thrust your employees into AI-first ultimatums, this is what you get: slop to prove that they&#8217;re indeed using AI. That&#8217;s not delivering any value.</p><blockquote><p><strong>The most important thing:</strong> Have a cohesive strategy about how you use AI across the enterprise. We firmly believe that it should be one or two agentic platforms and not one on each SaaS platform. Having teams on the same platform allows you to have a cohesive, unified, understandable framework that teams can use to speak to each other.</p></blockquote><h3>Measure What Matters</h3><p>We shouldn&#8217;t focus on the number of agents we have in production, but rather the quality of them and what value they&#8217;re delivering based on measurable results.</p><p>Focusing on the number of agents is like focusing on the vanity metrics of the 2000s. We focused on website visitors and session length, not what really mattered: conversion. You can have a million visitors, and if none convert, it&#8217;s worthless. Same thing with agents. You can have thousands running, but if you can&#8217;t tell their impact, you&#8217;re just spending money and time building and maintaining them, likely just so you can tell your boss or your board that you&#8217;ve indeed rolled out AI.</p><p><strong>Smart players in the agentic future will:</strong></p><ul><li><p>Focus on expanding the pie, not fighting over budget and territory</p></li><li><p>Work with teammates and other departments collaboratively</p></li><li><p>Avoid the &#8220;Shadow IT&#8221; sprawl that plagued 2010-era SaaS adoption</p></li><li><p>Build extensible and modular platforms, not bolt-on solutions</p></li></ul><p>Because in many ways, RevOps is seeing &#8220;Shadow IT&#8221; for the first time, the same way that IT saw it on the rise in 2010. The stepping around teams caused massive sprawl and inefficiencies then, and it&#8217;s going to cause it now.</p><h2>Think Like a Product Engineering Team</h2><p>Thinking about AI enterprise-wide allows you to be nimble and agile, adapting with the next waves in technology that will happen. If one SaaS platform folds, you&#8217;re okay. You know that you can rebuild around another area (assuming that your platform of choice doesn&#8217;t fold).</p><p>However, if you&#8217;re locked in with each vendor&#8217;s agentic platform, you have to rebuild each time. That&#8217;s real time and money lost. Worse, you&#8217;re at the mercy of each vendor&#8217;s AI strategy. If one lags, then you lag behind your competitors.</p><p><strong>The extensible architecture approach:</strong></p><p>Stop cramming all of your data into one SaaS vendor like you have in the past. The irony of vibe coding is that most of the vibes are spent building inside the box rather than outside of it. Think like a product engineer and realize that we diversify our tech for a reason. We choose the right tool for the right job.</p><ul><li><p><strong>Storage like S3</strong> is amazing and allows you to connect your files to all tools (and ingest into your vector database)</p></li><li><p><strong>Databases like Postgres</strong> allow you to render information that any of your tools can use, and display that information elsewhere (this is agentic-friendly!)</p></li><li><p><strong>Use vibe coding to extend your platforms</strong>, not replace strategic thinking</p></li><li><p><strong>Learn patterns like SQS/SNS or Redis caching</strong> to save money on AI builds and decrease latency</p></li></ul><p>You wouldn&#8217;t vibe your company&#8217;s selling strategy. Don&#8217;t vibe how you run your business.</p><h2>The Window Is Closing</h2><p>Here&#8217;s what most executives miss: the decisions you make about AI architecture in the next 12-18 months will determine whether you&#8217;re nimble or paralyzed for the next decade. This doesn&#8217;t mean that you have to rush into execute, but it&#8217;s time to begin experimenting and figuring out what is right for <strong>your</strong> comany.</p><p>Every platform-specific agent you build today is technical debt tomorrow. Every department that spins up their own AI solution is another silo you&#8217;ll have to untangle later. Every vendor lock-in you accept is leverage you&#8217;re handing over in future contract negotiations.</p><p>The companies winning in three years won&#8217;t be the ones with the most agents in production. They&#8217;ll be the ones who built extensible, modular, enterprise-wide platforms that let them pivot when the technology shifts; and it will shift.</p><p>They&#8217;ll be the ones whose RevOps team can publish a tool that Engineering reuses the next day. Whose Finance models feed directly into Sales forecasting without custom integration work. Whose cross-functional teams speak the same language because they&#8217;re working on the same platform.</p><p><strong>Your competitors are making their architecture decisions right now.</strong> Some are building on quicksand with vendor-specific solutions. Others are thinking holistically, bringing their people along for the ride, and realizing how powerful unified platforms can be to tear down barriers.</p><p>Which camp are you in?</p><div><hr></div><p><strong>Want help navigating this transition?</strong> I work with CFOs, CTOs, CIOs, and RevOps leaders to design enterprise-wide AI strategies that avoid vendor lock-in and actually deliver measurable value. <strong><a href="http://rightsized.tech/contact">Let&#8217;s talk about your architecture</a></strong>.</p><p><strong>Subscribe to get insights like this in your inbox</strong> and stay ahead of the AI platform wars. </p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://musings.rightsized.tech/subscribe?"><span>Subscribe now</span></a></p>]]></content:encoded></item><item><title><![CDATA[Quote to Cash: The Revenue Engine Nobody Understands ]]></title><description><![CDATA[Quote to Cash (Q2C) drives revenue but creates chaos when teams don&#8217;t understand it. Break down silos between Sales, RevOps, and Finance with this practical guide to CPQ, billing, and revenue operations.]]></description><link>https://musings.rightsized.tech/p/quote-to-cash-the-revenue-engine</link><guid isPermaLink="false">https://musings.rightsized.tech/p/quote-to-cash-the-revenue-engine</guid><dc:creator><![CDATA[Matt Pieper (Right Sized Tech)]]></dc:creator><pubDate>Tue, 30 Sep 2025 14:42:09 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/8f188832-45ba-4b07-aab3-0ad695b586b3_2700x2160.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Quote to Cash (Q2C) is one of the most frequently discussed topics in RevOps and GTM circles. A quick search will yield tons of posts and content about it, but usually through the lens of &#8220;<strong>buy this software</strong>&#8221; rather than &#8220;<strong>understand this process</strong>.&#8221;</p><p>Here&#8217;s the thing: even though Q2C is a critical component of any business - especially in SaaS - it&#8217;s often misunderstood. Worse, the individual components get locked behind silos and functions, creating a game of telephone between RevOps, Sales, Systems, and Finance.</p><p>The result? We far too often see breakdowns in handoffs across teams. Invoices go out wrong. Discounts don&#8217;t track. Revenue gets leaked. And billing operations - despite being critical to actually getting paid - gets dismissed as &#8220;<strong>someone else&#8217;s problem.</strong>&#8221;</p><p>In this post, I will break down some of that confusion and make Q2C a bit more accessible. Because when your teams actually understand how quoting connects to billing, which connects to cash in the door, everything runs smoother.</p><h2>What Actually Is Quote to Cash?</h2><p>Quote to Cash is the end-to-end process of how a deal becomes revenue in your bank account. It starts when a sales rep creates a quote for a customer and ends when that customer&#8217;s payment hits your books and gets recognized as revenue (timing, of course, depending on cash vs accrual).</p><p>Simple in concept. Messy in execution.</p><p>The reason it&#8217;s messy is that Q2C isn&#8217;t one thing - it&#8217;s a chain of connected processes that often live in different systems, managed by different teams, with different data models. When those connections break, your revenue engine sputters.</p><div class="pullquote"><p>Get this wrong and you&#8217;ll spend an eternity chasing down incorrect invoices and processing refunds.</p></div><h2>The Core Components of Q2C</h2><p>Quote to Cash can be broken down into five discrete components:</p><ol><li><p><strong>Quoting (CPQ)</strong> - What products the customer is buying, at which price, and for how long</p></li><li><p><strong>Billing</strong> - The invoice that goes out to a customer requesting payment</p></li><li><p><strong>Payment Gateway</strong> - How customers actually pay you (credit card, ACH, wire)</p></li><li><p><strong>Revenue Recognition</strong> - Recording revenue according to ASC 606 accounting rules</p></li><li><p><strong>Lifecycle Management</strong> - Tracking upsells, downsells, renewals, and cancelations over time</p></li></ol><p>One thing you&#8217;ll notice: I&#8217;m leaving out all of the selling operations. That&#8217;s deliberate. For clarity, we&#8217;re focusing on the happy path here - a successful deal leading to revenue. The messy stuff like lost deals, discount approvals, and commission disputes are important, but they&#8217;re part of a larger operation.</p><h2>Getting Our Terms Straight</h2><p>Before we dive deeper, let&#8217;s define some terms that get thrown around interchangeably but shouldn&#8217;t:</p><p><strong>Quote</strong> - A proposal document showing what products/services you&#8217;re offering, at what price, for what term. Not binding until accepted. This is typically what the customer receives from a rep.</p><div class="pullquote"><p>the quoting piece is what generates the order and ultimately determines what a customer has to pay</p></div><p><strong>Order</strong> - The finalized, accepted version of a quote. This is what the customer has actually agreed to buy and what drives billing. Think of it as the contract&#8217;s shopping cart.</p><p><strong>Contract</strong> - The legal agreement governing the relationship. Contains the order details plus all the legal terms, signatures, etc. This is typically an MSA/SOW, but in the Q2C space this is a revenue contract, legacy terms from Salesforce CPQ and ERPs. Still applicable for most professional services or physical assets, but dated under a subscription model.</p><p><strong>Opportunity</strong> - Your CRM&#8217;s tracking record for a potential deal. Lives in Salesforce/HubSpot and represents the <em>possibility</em> of an order.</p><p><strong>Termed</strong> - A subscription or contract with a defined end date (e.g., 12-month agreement ending December 31, 2025)</p><p><strong>Evergreen</strong> - A subscription that continues indefinitely until canceled, typically on a month-to-month basis. Think of your Netflix subscription here.</p><p>These distinctions matter because your CPQ, CRM, and billing systems all treat these differently. When your rep talks about &#8220;<strong>the contract</strong>&#8221; and your billing team talks about &#8220;<strong>the order</strong>,&#8221; they might be looking at completely different things.</p><h2>Quoting: Where Revenue Gets Made (Or Lost)</h2><p>This is the bread and butter of the entire operation. You&#8217;ve likely heard of tools like Salesforce CPQ (formerly Steelbrick), <a href="https://nue.io/">Nue</a>, <a href="https://dealhub.io/">DealHub</a>, and <a href="https://www.salesforce.com/sales/revenue-lifecycle-management/">Salesforce Revenue Cloud </a>that provide quoting functionality.</p><p>The core purpose of a quoting engine should be to:</p><h4><strong>Maintain Your Product Catalog</strong></h4><ul><li><p>What products you sell</p></li><li><p>How much they cost</p></li><li><p>How they&#8217;re sold together (bundles, required add-ons)</p></li><li><p>Pricing tiers and volume discounts</p></li></ul><h4><strong>Generate Quotes</strong></h4><ul><li><p>What products are sold to this customer</p></li><li><p>For how long (12 months, 24 months, evergreen)</p></li><li><p>Billing details (annual upfront, monthly in arrears)</p></li><li><p>Discounting and promotions</p></li></ul><h4><strong>Orchestrate Approvals</strong></h4><ul><li><p>Route exceptions through approval workflows</p></li><li><p>Track why discounts were given</p></li><li><p>Generate the final quote document</p></li></ul><h4><strong>Report on Deal Structure</strong></h4><ul><li><p>What&#8217;s being sold and at what discount</p></li><li><p>Win rates by product</p></li><li><p>Average deal size and term length</p></li></ul><p>This is the piece that takes the most time to get right because you&#8217;re dealing with lots of different stakeholders and representatives. Get this wrong and you&#8217;ll spend an eternity chasing down incorrect invoices and processing refunds. Trust me, I&#8217;ve been there.</p><p>Here&#8217;s what most people miss: <em><strong>the quoting piece is what generates the order and ultimately determines what a customer has to pay</strong></em><strong>.</strong> If it&#8217;s not on the quote, you can&#8217;t track it or invoice it. Period.</p><p>This is also where you&#8217;ll leak revenue if you don&#8217;t have insight into:</p><ul><li><p>Why reps are issuing discounts</p></li><li><p>Whether promotions are being tracked correctly</p></li><li><p>If you can use the same platform for Seller Led Growth (SLG) and Product Led Growth (PLG)</p></li></ul><p>And if you can&#8217;t customize your quoting quickly, you lose speed to market. Waiting for your CPQ team to build products means you delay launches or lose time on pricing experiments.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Enjoying so far? Subscribe to stay up to date.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><h3>The Order: Where Quoting Meets Billing</h3><p>When a quote is accepted and finalized, it should generate a finalized <strong>order</strong> that represents what the customer should receive. This order is what gets sent to your billing platform.</p><p>This is the handoff point where things often break. If you have disconnected quoting and billing systems (like Salesforce CPQ feeding into <a href="https://www.netsuite.com/portal/products/erp/financial-management/billing.shtml">NetSuite</a>, <a href="https://stripe.com/">Stripe</a>, or <a href="https://www.sage.com/en-us/sage-business-cloud/intacct/product-capabilities/extended-capabilities/subscription-billing/?referral=grfcpa">Sage Intacct</a>), you&#8217;ll usually need to build integrations. And if your business has special structures - like usage-based pricing, multi-year deals with annual increases, or complex proration rules - those integrations can get gnarly fast.</p><h2>Revenue Recognition: The Accountants&#8217; Obsession</h2><p>If you&#8217;re in the US and selling subscriptions, you&#8217;ll likely need to account for Revenue Recognition (RevRec) in accordance with <a href="https://schwindtco.com/resources/articles/accounting/revenue-from-contracts-with-customers-fasb-asc-606/">FASB ASC 606</a>. This is especially true if you&#8217;re following accrual accounting (which you are if you&#8217;re past the lemonade stand stage).</p><p>Why does this matter?</p><p>Because ASC 606 requires you to recognize revenue when you <em>deliver</em> the service, not when the customer <em>pays</em> you. This is critical in multi-term agreements where the customer pays for 12 months upfront, but you don&#8217;t deliver the service until it&#8217;s actually used each month.</p><p>Example: Customer pays you $12,000 on January 1st for an annual subscription. You can&#8217;t book all $12,000 as January revenue. You have to spread it ratably over 12 months at $1,000/month.</p><p>If you&#8217;re not in finance or accounting, this probably hasn&#8217;t crossed your radar. But it&#8217;s important to your auditors and investors, and it affects how you report growth metrics.</p><p>There&#8217;s actually a whole host of other accounting considerations that apply in Q2C - such as MEA (<a href="https://quickbooks.intuit.com/r/enterprise/multi-entity-accounting/">Multi-Entity Accounting</a>) for companies with complex legal structures - but I don&#8217;t want to bog this down in the technical weeds.</p><p>RevRec is typically handled by your accounting software (NetSuite, Sage Intacct, <a href="https://www.rillet.com/product/advanced-revenue-recognition">Rillet</a>), a third-party tool (<a href="https://www.rightrev.com/">RightRev</a>), or spreadsheets (please don&#8217;t). Your billing tool doesn&#8217;t necessarily have to be the RevRec tracker since any platform that can ingest order data can typically track RevRec schedules.</p><h2>Billing: The Thing You Only Notice When It&#8217;s Broken</h2><p>Billing is like the CIA - you should only hear about it when something goes wrong. Unfortunately, a lot of us spend way too much time hearing about it.</p><p>A bad billing setup will set your team back in terms of productivity and customer trust. Managing refunds and credits can spiral out of control quickly, and every billing error erodes confidence in your operations.</p><p>In a perfect world, your billing engine takes the inputs from your quoting engine and generates an invoice automatically. In this perfect world, your billing engine doesn&#8217;t need translation and everything is fully in sync, reducing complexity.</p><div class="pullquote"><p>The key is understanding how your quoting engine connects to your billing engine and what data is needed at each handoff. </p></div><p>However, far too often the order data must be sent to a third-party platform and requires customization. That customization usually involves translating order data to billing data, especially when we get to how each platform calculates things like <strong>proration</strong>.</p><p>Different systems use different proration methodologies, which causes annoying rounding errors. Speaking of rounding errors, the granularity in how each platform tracks decimal points (2 decimals vs 4 decimals) can also cause invoice discrepancies that make your finance team want to quit.</p><h3>How Billing Actually Works</h3><p>Your billing engine will generate invoices at a regular cadence (monthly, quarterly, annually) or as one-time invoices for professional services or setup fees. These invoices get sent to your customer and paid through whatever methods you have in place - whether that&#8217;s through your application, a customer portal, or a payment link on the invoice itself.</p><p>Some billing software - like Sage Intacct - can generate these invoices either through a <strong>contract</strong> (which drives a recurring cadence automatically) or through an <strong>order</strong> (one-time generation). Which you choose depends on your business needs and the capabilities of your billing platform.</p><p>Common billing platforms include:</p><ul><li><p>NetSuite Suite Billing</p></li><li><p>Nue.io </p></li><li><p>Sage Intacct</p></li><li><p>Zuora</p></li><li><p>Chargebee</p></li><li><p>Stripe Billing</p></li><li><p>Salesforce Billing</p></li><li><p>DealHub</p></li></ul><h2>Payment Gateway: How Money Actually Moves</h2><p>Your payment gateway is the system that processes payments from customers through a payment processor. Not rocket science, but critical infrastructure.</p><p>Payment gateways are typically platforms like Stripe, <a href="http://authorize.net/">Authorize.net</a>, or <a href="https://www.paypal.com/us/braintree">Braintree</a>. They can usually process both credit card and ACH payments, with some handling international payment methods.</p><p>Technically, a payment gateway isn&#8217;t <em>necessary</em> since you can still receive payments through manual transfers, checks, or wire. But at scale, this is essential for credit card processing and overall efficiency. Plus, automated payment collection dramatically improves your cash flow and reduces Days Sales Outstanding (DSO).</p><p>The key is making sure your payment gateway integrates with your billing system so that when a payment is processed, it automatically reconciles against the invoice. Manual payment matching is a special kind of operations hell.</p><h2>Lifecycle Management: Keeping Track of What Customers Have</h2><p>Lifecycle Management keeps track of what the customer is entitled to and allows you to make changes over time. This could be subscriptions, physical assets (hardware), or even professional services allocations.</p><p>Ideally, your lifecycle manager allows you to:</p><ul><li><p><strong>Upsell</strong> - Add products or increase quantity mid-term</p></li><li><p><strong>Downsell</strong> - Remove products or decrease quantity</p></li><li><p><strong>Renew</strong> - Extend the contract for another term</p></li><li><p><strong>Cancel</strong> - Terminate the subscription</p></li><li><p><strong>Track assets</strong> - Monitor physical devices or license keys</p></li></ul><p>This tracking makes customer support&#8217;s lives easier and allows you to provide automated provisioning/deprovisioning of entitlements to your application. Your customers receive access to exactly what they pay for - no more, no less - while reducing manual work for your operations teams.</p><p>Good lifecycle management also feeds your revenue forecasting. If you can&#8217;t see what&#8217;s up for renewal in Q4, you can&#8217;t build an accurate plan.</p><h2>How It All Connects: The Q2C Flow</h2><p>Here&#8217;s how these pieces fit together in practice:</p><ol><li><p><strong>Rep creates quote</strong> in CPQ with products, pricing, terms</p></li><li><p><strong>Quote gets approved</strong> through workflow (if discounts exceed thresholds)</p></li><li><p><strong>Customer accepts quote</strong> &#8594; becomes an Order</p></li><li><p><strong>Order flows to billing system</strong> (either natively or through integration)</p></li><li><p><strong>Billing system generates invoice</strong> according to billing frequency</p></li><li><p><strong>Invoice sent to customer</strong> with payment link</p></li><li><p><strong>Customer pays</strong> through payment gateway</p></li><li><p><strong>Payment reconciles</strong> against invoice in billing system</p></li><li><p><strong>Revenue recognition schedule</strong> spreads revenue over delivery period</p></li><li><p><strong>Lifecycle manager tracks</strong> the subscription for future changes</p></li></ol><p>When this flow works smoothly, it&#8217;s beautiful. When it breaks at any handoff point, you get chaos: duplicate invoices, missing payments, revenue leakage, and angry customers.</p><h2>Choosing Your Q2C Stack</h2><p>The bottom line is that there are multiple ways to manage your Q2C process. The right approach depends on:</p><ul><li><p><strong>Complexity of your business</strong> - Usage-based pricing? Multi-entity? International?</p></li><li><p><strong>Reporting requirements</strong> - What does your CFO need to see?</p></li><li><p><strong>In-house knowledge</strong> - Do you have Salesforce admins? NetSuite consultants?</p></li><li><p><strong>Platforms you already have</strong> - Sometimes the best tool is the one you already own</p></li></ul><p>The key is understanding how your quoting engine connects to your billing engine and what data is needed at each handoff. These don&#8217;t have to be the same platform, but when you have a unified data model (like Nue, where quoting and billing share the same database), the entire process is more reliable and requires less maintenance.</p><p><strong>Unified platforms</strong> (Nue, Zuora, Chargebee) give you tight integration but may lack flexibility in one area or another.</p><p><strong>Hub and Spoke Stacks</strong> (Salesforce CPQ + NetSuite, DealHub + Intacct) give you powerful individual tools but require integration work and ongoing maintenance. Often causing more maintenance work.</p><p>There is no one-size-fits-all approach. The right answer depends on your specific business model, team capabilities, and growth stage.</p><h2>What&#8217;s Next</h2><p>Understanding Q2C is the first step. Implementing it well is the hard part. If your team is struggling with:</p><ul><li><p>Revenue leakage from incorrect invoices</p></li><li><p>Manual processes that don&#8217;t scale</p></li><li><p>Disconnected systems that require constant reconciliation</p></li><li><p>Lack of visibility into what&#8217;s actually been sold</p></li></ul><p><a href="http://rightsized.tech">Right Sized Tech</a> can help shepherd your team through the process and determine what&#8217;s best for your business. We&#8217;ve implemented Q2C stacks for companies from seed stage to Series C and beyond.</p><p>Because at the end of the day, Quote to Cash isn&#8217;t about software - it&#8217;s about getting paid accurately for what you sell. Everything else is just details.</p><div><hr></div><p><strong>Related Reading:</strong></p><ul><li><p>How to Choose Between Unified and Best-of-Breed Q2C Stacks [coming soon]</p></li><li><p>Common Revenue Leakage Points in SaaS Billing [coming soon]</p></li><li><p>CPQ Implementation Checklist for RevOps Teams [coming soon]</p></li></ul><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">We love to talk about scaling your systems. Subscribe today to get tips.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[The Tech Industry's Recurring "Get Rich Quick" Playbook]]></title><description><![CDATA[How Companies Manufacture Job Titles to Build Sales Armies]]></description><link>https://musings.rightsized.tech/p/the-tech-industrys-recurring-get</link><guid isPermaLink="false">https://musings.rightsized.tech/p/the-tech-industrys-recurring-get</guid><dc:creator><![CDATA[Matt Pieper (Right Sized Tech)]]></dc:creator><pubDate>Wed, 24 Sep 2025 19:25:54 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/c1e1c084-f71b-48f8-8ff3-eebe1e7410d3_2160x2700.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p><em>A pattern I've witnessed repeat across 15 years in tech, and why you should be skeptical of the latest career "opportunity."</em></p><h2>The Promise</h2><p>Scroll through LinkedIn and you'll see them: slick posts promising you can make $100k with "just a few workflows." Join this course, learn this tool, and you too can become a "GTM Engineer" or whatever the latest hot title happens to be.</p><p><strong>The problem?</strong> Most of these influencers have never actually done the work they're selling. They got lucky, spotted a trend, and are now capitalizing on your career anxiety.</p><p>I've watched this exact playbook unfold multiple times over the past 15 years, since the start of the &#8220;Shadow IT&#8221; trend. The current wave around n8n, Clay, and the "GTM Engineer" phenomenon has given me a fresh perspective on how sophisticated (and damaging) this cycle has become.</p><h2>The Playbook: How Companies Manufacture Expertise</h2><p>Here's how it works, step by step:</p><h4>Stage 1: Early Success</h4><p>A company launches and starts landing customers. Sales are good, but there's a problem&#8212;customers need constant hand-holding to unlock the product's "full potential."</p><h4><strong>Stage 2: The Title Invention</strong></h4><p>To augment its implementation partners, the company invents a new job category. "Salesforce Administrator." "CPQ Architect." "GTM Engineer." They position this as a revolutionary new way of working.</p><p><em>What's really happening:</em> They're planting sales agents in customer organizations without anyone realizing it.</p><h4>Stage 3: The Recruitment</h4><p>The company recruits operators and pushes positioning through partner channels. They build social presence&#8212;they're the cool new kids disrupting everything.</p><h4>Stage 4: The Loyalty Engine</h4><p>The people hired into these roles become emotionally invested. The vendor gave them their career, so they champion every new feature. They create content for free. They recruit friends into the "movement."</p><h4>Stage 5: Legitimacy Through Certification</h4><p>Certifications roll out. Now it's official; there are "professionals" who need "education." The company gains street credibility and an army of implementers.</p><h4>Stage 6: The Ecosystem</h4><p>An entire economy springs up: certification trainers, "make $200k as a consultancy" courses, and content creators. We see course after course spin up to prepare people for the certifications at stage 5. We see test dumps emerge and companies selling prep materials. Consultancies abound to help you implement, maintain, and optimize.</p><p>Everyone's making money, everyone's invested in the flywheel.</p><h2>The Inevitable Crash</h2><p>Years pass. The company goes public, and the founders get rich. Quality degrades as focus shifts from product to revenue. Prices increase. The tool becomes increasingly difficult to use as it goes up market and the company chases revenue generating features, what was once easy now requires workarounds.</p><p>The market saturates. Jobs disappear. But nobody blames the hypesters who oversold the opportunity.</p><div class="pullquote"><p>Make sure you're not left holding the bag.</p></div><p><strong>The victims?</strong> People who believed they could career-switch into something transformational, only to find themselves holding certificates for roles that no longer exist, salaries plummeting, or never really existed in the first place.</p><h2>Current Example: The "GTM Engineer"</h2><p>Take a closer look at the "GTM Engineer" trend. Notice how:</p><ul><li><p><strong>No two job descriptions match</strong>: the role is completely nebulous</p></li><li><p><strong>No standards exist</strong> for what constitutes "engineering excellence" in this context</p></li><li><p><strong>The influencers</strong> promoting it often lack actual engineering or GTM experience</p></li><li><p><strong>It's rebranded work</strong> that Growth Hackers, MarTech engineers, and RevOps teams have done for years, but now it&#8217;s accessible to the masses through AI and an intuitive canvas.</p></li><li><p><strong>The term &#8216;Engineer&#8217; </strong>is about as nebulous as the term &#8216;Operations&#8217;</p></li></ul><p><em>Real engineering isn't about automating things.</em></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Enjoy this post? Subscribe to stay up to date with new posts.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p></p><h2>Red Flags: How to Spot the Frauds</h2><p><strong>Check their background:</strong></p><ul><li><p>Does their job history actually include the role they're teaching?</p><ul><li><p>Do they walk the walk or only talk the talk?</p></li></ul></li><li><p>Is their profile littered with hype?</p></li><li><p>Are they capitalizing on a trend without relevant experience?</p></li><li><p>Do they only promote one vendor's approach?</p></li></ul><p><strong>Question the narrative:</strong></p><ul><li><p>Are they acknowledging cheaper, open-source alternatives?</p></li><li><p>Do they discuss failure modes and challenges?</p></li><li><p>Is their content overly focused on income potential?</p></li></ul><p><strong>Look at the ecosystem:</strong></p><ul><li><p>Is there a certification program that launched suspiciously quickly?</p></li><li><p>Are there suddenly dozens of "experts" with similar messaging?</p></li><li><p>Does criticism get dismissed rather than addressed?</p></li></ul><h2>The Human Cost</h2><p>This isn't just about bad career advice. Real people make major life decisions based on these manufactured opportunities. They:</p><ul><li><p>Leave stable careers for trending roles</p></li><li><p>Pay thousands for courses and certifications</p></li><li><p>Build identities around tools that may not survive market shifts</p></li><li><p>Face career disruption when the bubble bursts</p></li></ul><h2>What Companies Won't Tell You</h2><p><strong>The alternatives exist.</strong> For every hyped tool, there are usually:</p><ul><li><p>Open-source options that cost nothing</p></li><li><p>Established enterprise solutions with proven track records</p></li><li><p>Simpler approaches that don't require specialized roles</p></li><li><p>Skills that you can acquire and apply across various domains.</p></li></ul><p><strong>But acknowledging this doesn't serve the vendors' motivation to create dependency.</strong></p><h2>Moving Forward</h2><p>I'm not saying all new job categories are scams; genuine innovation does create new roles. But approach the hype with healthy skepticism:</p><ul><li><p><strong>Demand substance over flash:</strong> Look for detailed case studies, not just income promises</p></li><li><p><strong>Seek diverse perspectives:</strong> Find practitioners who aren't selling something</p></li><li><p><strong>Question the timeline:</strong> Sustainable careers aren't built in months</p></li><li><p><strong>Value transferable skills</strong> over vendor-specific expertise</p></li></ul><p>The "get rich quick" mafia will move on to the next trend when this one burns out. Make sure you're not left holding the bag.</p><div><hr></div><p><em>Have you witnessed this pattern in your industry? The cycle continues because it works, but only for the people at the top, or those who get in early.</em></p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/p/the-tech-industrys-recurring-get/comments&quot;,&quot;text&quot;:&quot;Leave a comment&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://musings.rightsized.tech/p/the-tech-industrys-recurring-get/comments"><span>Leave a comment</span></a></p><p></p>]]></content:encoded></item><item><title><![CDATA[CPQ is End Of Sale: Where Should You Go?]]></title><description><![CDATA[A Review of The Current CPQ and RLM Landscape]]></description><link>https://musings.rightsized.tech/p/cpq-is-end-of-sale-where-should-you</link><guid isPermaLink="false">https://musings.rightsized.tech/p/cpq-is-end-of-sale-where-should-you</guid><dc:creator><![CDATA[Matt Pieper (Right Sized Tech)]]></dc:creator><pubDate>Mon, 15 Sep 2025 22:56:19 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/83543e60-8f42-4036-9af0-3b1dfff316df_3840x2160.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Salesforce announced the end of sale (EOS) for CPQ a few months ago after years of no new features being released for the sixteen-year-old product.</p><p>There's not a week that goes by that someone asks me what they should do with Salesforce CPQ (Steelbrick aka CPQ) or which billing solution they should go with, or if they should go with Salesforce Revenue Cloud Advanced (fka RLM fka Revenue Cloud aka RCA).</p><p>The answer is that there's not a concrete go-to for everyone, or even a best practice. The answer is that it's usually the best one for your business.</p><p>There are tools that are considered "best in class" by many analysts, but they don't work for everyone.</p><p>There are tools that are overbuilt because they're built for specific use cases. Such as integrating into Commerce Cloud for a Fortune 100.</p><p>There are only 100 companies in the Fortune 100 and 3000 CPQ customers.</p><p>We're biased at Right Sized Tech; we focus on startups and SMBs, so we tend to lean towards products that work with minimal support. The teams we support are usually already stretched thin, so we want to avoid wasting time with workarounds or complex setups. Keep it simple is our mantra.</p><p>The criteria we use when selecting tools are:</p><ul><li><p>How easy/quick is it to implement? Time is money</p></li><li><p>How easy is it to maintain?</p></li><li><p>Which persona maintains it? Engineering, RevOps? What skill level</p></li><li><p>Can it be used for PLG and Direct Sales?</p></li><li><p>How complete is the API?</p></li><li><p>How extensible/customizable is it?</p></li><li><p>Can it handle billing?</p></li><li><p>Can it handle usage?</p></li><li><p>What is the integration landscape?</p></li></ul><p>As an SMB/Midmarket organization, we focused on companies under 5k employees and with varying revenue. When we looked at the market for viable replacements, we identified the following companies:</p><ul><li><p><a href="https://dealhub.io/">DealHub</a></p></li><li><p><a href="https://www.logik.io/salesforce">Logik</a> (now part of ServiceNow)</p></li><li><p><a href="https://www.nue.io/">Nue.io</a></p></li><li><p><a href="https://www.salesforce.com/sales/revenue-lifecycle-management/">Salesforce RCA</a></p></li></ul><p>We considered including Sage Intacct and SuiteBilling, but determined that the average customer that Right Sized Tech serves will not fall into these categories.</p><p>We'll explore the high-level pros and cons of each below, and declare a winner. But we want to know what you think as well.</p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/p/cpq-is-end-of-sale-where-should-you/comments&quot;,&quot;text&quot;:&quot;Leave a comment&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://musings.rightsized.tech/p/cpq-is-end-of-sale-where-should-you/comments"><span>Leave a comment</span></a></p><h2><strong>Salesforce RCA</strong></h2><p>Salesforce Revenue Cloud Advanced (RCA), formerly known as Revenue Lifecycle Management (RLM), is billed as a revenue management platform built on Salesforce.</p><p>RCA is strongly coupled with Commerce Cloud, so it makes logical sense to choose if this is something you fully support. From a product engineer's perspective, it is challenging to onboard with Salesforce's APIs if you're not familiar with them - but this is nothing new, compared to other RESTful APIs in the industry. However, if you're an enterprise customer and not a startup or SMB, this is probably something you've likely solved for.</p><p>Salesforce is working closely with partners and others in the market to inform its roadmap and has built a billing solution alongside quoting. You can use all the standard automations that Salesforce has, as well as approvals.</p><p>The current issue with RCA is that it's shrouded in mystery. I feel like Nicolas Cage will appear in a film where his objective is to find the documentation for RCA. Even though it was rebranded at Dreamforce '24, it's still listed as <a href="https://www.salesforce.com/sales/revenue-lifecycle-management/">Revenue Lifecycle Management</a>, which is confusing.</p><p>RCA is quite complicated, and there isn't a readily available talent pool to bring on the client side, so you'll lean on a partner for most of the implementation and further maintenance. Which, from my experience, isn't much of a selling point in the SMB space.</p><p>The other interesting component is that while folks are grumbling in one-on-one conversations about it, the product is heavily lauded by those same folks in public. So, make sure to vet your partners to ensure that they have your best interests in mind, not those of a channel partner.</p><p>Salesforce Ben released an article in May 2025 that details RCA further in <a href="https://www.salesforceben.com/your-guide-to-salesforce-revenue-cloud/">this article</a>.</p><h2><strong>Logik</strong></h2><p>Acquired by ServiceNow, and ServiceNow has publicly stated:</p><blockquote><h4><em><strong>A NOTE ON THE SERVICENOW ACQUISITION</strong></em></h4><h4><strong>Continued cooperation with Salesforce</strong></h4><p>Salesforce is a trusted partner of Logik.ai, and we remain dedicated to supporting our shared customers. Our standalone CPQ and advanced configurator will continue to seamlessly integrate with Salesforce CRM, Salesforce CPQ (Steelbrick), RLM/RCA, and Commerce Cloud. We plan to maintain our ISV partnership status and are actively growing our team of Salesforce developers and engineers to further strengthen and expand our integration with the Salesforce ecosystem.</p></blockquote><p>While it is reassuring to see this, we must exercise caution as to whether Logik will continue to support Salesforce in the long run. Given the public antagonism towards ServiceNow's competitor, we cannot predict whether they'll use deplatforming as a threat, nor do we know what contractual terms are in place.</p><p>Like RCA, Logik has a strong integration with eCommerce, with a strong Shopify and Salesforce integration.</p><p>Logik has powerful tooling, and we recommend it as more of a configure and price platform that has quoting. The UI leaves something to be desired and reminds us of the clunky UI of the legacy enterprise software it sits upon.</p><p>While it's a strong offering, it's not one we would typically recommend if choosing to move off of Salesforce CPQ, as there are other products with more incentives to improve upon their Salesforce experience.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Want to stay up to date with Business Systems and the Quote-to-Cash space? </p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p></p><h2><strong>DealHub</strong></h2><p>DealHub has been around since 2014, one year before the acquisition of Steelbrick by Salesforce, and five years after Steelbrick entered the scene, and is a Series C company.</p><p>They have a wealth of experience in the space and have had time to build out their integrations. They are a cross-platform CPQ serving HubSpot, Salesforce, Dynamics, and Freshworks with integrations to DocuSign, Slack, and Gong.</p><p>They offer integrated billing but no out-of-the-box subscription management. This approach may work for many businesses or those that don't need to manage subscriptions, but it puts them at a disadvantage compared to most SaaS companies.</p><p>The API is strong and can be used headless, and the documentation is good, which makes this engineer smile. It's been a while since we've been hands-on with the product, so we're supplementing our experience with documentation and customer interviews.</p><p>DealHub offers contract management (CLM), configure price quote (CPQ), deal room, and billing solutions. This is great for companies that want a one-stop shop experience and drives efficiency, but it does leave a watered-down experience compared to point solutions.</p><p>Overall, a strong offering and a competitor to CPQ, with a solid customer base and talent available on the market.</p><h2><strong>Nue.io</strong></h2><p>Nue is the relative new kid on the block, founded in 2019 but largely in stealth mode until the last few years. Nue has raised a Series B at this point and brought on an experienced CEO, Mark Walker.</p><p>Nue was founded by a team that knows the quote to cash space by the back of their hand. Cheng Zou and Tina Kung spanned across Zuora, Neocrm, Oracle CPQ, and Salesforce CPQ in engineering and product roles. This team knew the space, the problems, and how they wanted to tackle them.</p><p>We view Nue's competitive advantage as the Everything Billing platform and hybrid data model. Because the product is built with billing in mind, you have a unified experience from setting up the product catalog to building a quote.</p><p>Nue has a hybrid data model, and I think it's a strong differentiation. It means you get the speed and performance of a RESTful API directly with Nue's API, but also access to all standard Salesforce automations and features. This allows product engineering and RevOps or Salesforce teams to work with the features that best suit them and work independently.</p><p>There is no need to hire a CPQ Architect or Specialist; you can redeploy members of your existing team and get everyone up to speed.</p><p>Nue's team is customer-obsessed in an era where most companies prioritize efficiency and revenue protection. They realize that satisfied customers are a multiplier for growth, and the product team takes feedback seriously.</p><p>One of the most unique features that Nue has is the ability to preview an invoice during the quoting process. This allows your reps and customers to know that the next invoice will be correct and there are no surprises. That's a boost in potential NPS for your company.</p><p>Nue is still early and doesn't have everything ironed out quite yet. For example, if you're looking for extensive product rules such as "add X when Y is selected," they may not be the best choice for you yet.</p><p>But there is a reason that OpenAI and Anthropic are customers.</p><h2>The Winner</h2><p>At Right Sized Tech, we believe that Nue is the right tool for a large swath of customers looking to replace CPQ now that it is end of sale. We believe it has the best product vision, low-pressure sales tactics, and a strong current offering.</p><p>As with any tool, it may not be the best tool for every company, and that's where we fit it. We can have a strategic conversation with you about the pros and cons of each product and whether it is the right sized tech for your business.</p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://www.rightsized.tech/contact&quot;,&quot;text&quot;:&quot;Right Size Your Tech&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://www.rightsized.tech/contact"><span>Right Size Your Tech</span></a></p><p></p>]]></content:encoded></item><item><title><![CDATA[Welcome To The Journey]]></title><description><![CDATA[An exploration of tech, ADHD, photography, and growing a business.]]></description><link>https://musings.rightsized.tech/p/welcome-to-the-journey</link><guid isPermaLink="false">https://musings.rightsized.tech/p/welcome-to-the-journey</guid><dc:creator><![CDATA[Matt Pieper (Right Sized Tech)]]></dc:creator><pubDate>Mon, 15 Sep 2025 02:20:54 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!YOhI!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F88504595-64aa-46a6-b82a-a0ba728105b6_2700x2160.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Hello there, in case we&#8217;ve never met, let me introduce myself.  My name is Matt Pieper (pronounced &#8220;peeper&#8221;) and I reside in Columbus, Ohio. I&#8217;ve had the privilege of many amazing career and life experiences, including joining the US Army and deploying to combat zones, building software, leading engineers, and volunteering in disaster response in places like the Bahamas after Hurricane Dorian.</p><p>This vast background is highly likely due to my late-diagnosed ADHD, not knowing why I was drawn to novelty and chasing dopamine, but always enjoying the journey.</p><p>As a person, I enjoy traveling, being outside, photography, volunteering, and quality time with my wife, Adrian, and rescue pup Oscar.</p><h2>So, Why A Substack?</h2><p>For the last 5 or 6 years, I&#8217;ve posted on LinkedIn, where I&#8217;ve been told that my brand is &#8220;authentic&#8221; and &#8220;transparent&#8221;. But LinkedIn limits the way that we can express and post, and often, you&#8217;re at the life and death of the algorithm. Further, we lose the context over time of who is actually engaging with the content. I want to build and foster a community of readers who enjoy what I have to say and want to further a dialogue. Substack helps with that.</p><p>I started posting on LinkedIn as a way to express myself and explore topics with others. With my neurodivergent, hyperactive, often contrarian (thanks, ODD!) brain, I have constant thoughts rumbling through, aiming to grasp at each one. That same contrarian view prompts me to explore and question things in a different way than some. To question the why and if we should do something.</p><p>I also started posting as a way to learn how to tell stories better. We can have the greatest thoughts and experiences, but if we can&#8217;t captivate our audience, we have effectively died on the vine.</p><p>My posting started as a way to inform my coworkers through backchannels. I would find myself explaining the same thing over and over. I knew it was &#8220;best practices,&#8221; but it would fall on deaf ears. I engaged with the community in order to get a sanity check, but also social proof. The more that people interacted with my content, the more comments I received from my coworkers about it.</p><p>Substack allows for a variety of content and longer-form posts that the creator owns. It also allows me to find out who is reading and engaging, not just vanity hype metrics that social media drives.</p><p>It also made me realize that there are quite a few lurkers out there who read your content and appreciate it, but don&#8217;t have a way to express it.</p><h2>What I Write About</h2><p>Refer back to ADHD. </p><p>Look, I tend to break the rules about these kinds of things. All the influencers and books and such will tell you to have a focus, to write a content calendar, etc.</p><p>But that&#8217;s boring! I want to bring you along on the same journey that I have. It&#8217;s why I loved school. I took classes in the Ottoman Empire, History of Jazz, Entrepreneurship, Strategy, Corporate Finance, and more. Just because I love having a robust background to approach a problem.</p><p>But here are a few things I&#8217;m looking to explore:</p><ul><li><p><strong>Business Systems and RevOps</strong> - how we partner together, the different approaches we have, and why it&#8217;s a partnership, not an either/or. How RevOps and Engineering/Systems work together accelerates growth and makes us all better.</p></li><li><p><strong>Business Systems Approach</strong> - How We Can Build Better Processes and Integrate Software. How can we invest rather than spend? What teams should look like. How to assess team quality. When you should hire one. </p></li><li><p><strong>Procurement and Consultants</strong> - how to build a better procurement process and tell the story when you pitch. How to assess consultants and know when to bring them in.</p></li><li><p><strong>Salesforce</strong> - okay, okay, I know that&#8217;s what a lot of you are here for! Let&#8217;s explore quote to cash, maybe shitpost about CPQ a bit, but have an honest discussion of how we can make Salesforce better. Build the community the way we want, and also how to upskill.</p></li><li><p><strong>AI</strong> - not the hype, not the fluff, not a lot of technical details. However, the real-world risks, how I utilize AI in my business and life, what I advise clients to do, and how you can stay relevant.</p></li><li><p><strong>Business Journey</strong> - I&#8217;m building a business, and I want to share it with you and everyone else. The path to entrepreneurship seems to be rising as employees become disenfranchised with their employers, layoffs abound, and AI is threatening Skynet any day now. Let&#8217;s approach how I&#8217;m growing and how different it is from being in a startup or learning in school.</p></li><li><p><strong>Photography</strong> - This is my passion, and I want to share it with you. It informs how I go about my life, and I think it&#8217;s impactful.</p></li></ul><p>That&#8217;s a lot of topics, right?! But don&#8217;t worry, I don&#8217;t want to spam you. You&#8217;ll be able to pick and choose which of these areas you want to read about, and I&#8217;ll make sure to categorize them appropriately.</p><div class="image-gallery-embed" data-attrs="{&quot;gallery&quot;:{&quot;images&quot;:[{&quot;type&quot;:&quot;image/jpeg&quot;,&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/88504595-64aa-46a6-b82a-a0ba728105b6_2700x2160.jpeg&quot;},{&quot;type&quot;:&quot;image/jpeg&quot;,&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/12f20d49-fcd9-44e6-9d66-bc2fd8d5e8dc_3240x2160.jpeg&quot;},{&quot;type&quot;:&quot;image/jpeg&quot;,&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/dd068c6e-d86e-4ae5-9958-ed6bf2d98896_2700x2160.jpeg&quot;},{&quot;type&quot;:&quot;image/jpeg&quot;,&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/6dc9d795-1f6b-454e-bd1d-ea6f67276d04_2160x3240.jpeg&quot;}],&quot;caption&quot;:&quot;&quot;,&quot;alt&quot;:&quot;&quot;,&quot;staticGalleryImage&quot;:{&quot;type&quot;:&quot;image/png&quot;,&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/888b508f-845d-4273-8ee6-2e46966603c8_1456x1456.png&quot;}},&quot;isEditorNode&quot;:true}"></div><p></p><h2>My Promises To You, The Reader</h2><p>Everyone is using AI these days and we have started to see the same patterns of speech, our brains are excellent at pattern matching, and we know something is off. This is why I don&#8217;t write with AI, outside of editorial advice and general structure, and I promise you that this will continue. You receive the same stream of consciousness thoughts with minimal editing, which is my hallmark.</p><p>I do most of the research myself or pull from the deep thoughts of my brain, and then augment with AI where necessary. I enjoy diving into deep topics and reading about them. I don&#8217;t want to lose that joy by deferring to an oft-wrong robot.</p><p>I will engage with you to the limits that I can. You spend your time reading my thoughts. I'd like to hear your thoughts in return. Tell me what you disagree with, tell me what you love, and debate with me. I love conversations, let&#8217;s converse.</p><p>You&#8217;ll get honest, open takes. Sugar coating and hype don&#8217;t do anyone any good. If I end up posting sponsored content - a man has to eat! - It will always be my honest opinion, and I will never post about something I don&#8217;t agree with. That&#8217;s unfair to you, the person spending time building the community.</p><p>I&#8217;ll bring humanity to everything I write about. How what I write affects you, not the elite, robots, or world domination (unless we&#8217;re talking about a game of Risk!)</p><h2>Will This Change My LinkedIn Posts?</h2><p>Not really! Consider this space an extension of our regular engagement on social media. This will be a more in-depth exploration and follow a regular cadence. This will be where we can have a prolonged engagement, as opposed to one-off LinkedIn engagements.</p><p>Want to make sure someone hears about this change? </p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/p/welcome-to-the-journey?utm_source=substack&utm_medium=email&utm_content=share&action=share&quot;,&quot;text&quot;:&quot;Share&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://musings.rightsized.tech/p/welcome-to-the-journey?utm_source=substack&utm_medium=email&utm_content=share&action=share"><span>Share</span></a></p><h2>What&#8217;s Next?</h2><p>It&#8217;s a great question; the simple answer is: life. </p><p>This is a period in my life where I&#8217;m exploring what is important to me and where I want to invest my precious moments. </p><p>I&#8217;m getting the hang of this new medium, so I ask for patience. But I think together we&#8217;ll build something great here.</p><p>My ask to you? Never stop giving me feedback; iterating is how we improve, and growth is a human concept.</p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://musings.rightsized.tech/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://musings.rightsized.tech/subscribe?"><span>Subscribe now</span></a></p><p>To learn more:</p><p><a href="http://mattpieper.com">Photography Portfolio</a></p><p><a href="http://rightsized.tech">Fractional Business Systems Consulting</a></p><p><a href="http://linkedin.com/in/piepermatthew">LinkedIn</a></p><p></p>]]></content:encoded></item></channel></rss>