You See, I Was Never Supposed to Be in Tech
A Journey Interweaved With a SaaS Vendor
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.
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.
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.
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.
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.
You see, I never wanted to be in tech.
I still wanted to code and be interested in tech, but I didn’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 that good at math.
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.
The Day Everything Changed
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."
"What the f*** is Salesforce?" I said.
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.
And that's when I discovered something surprising.
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.
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.
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.
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.
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.
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.
I was never supposed to be in tech, but the community lured me away from my economics dream.
Growing Up Together
Over the next decade, both Salesforce and I evolved in parallel ways.
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.
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.
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.
We were both becoming more sophisticated, more polished, more professional. And there was nothing wrong with that evolution. It was necessary, even admirable.
But something was happening to both of us along the way.
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.
When the Party Changed
I look back at all the Dreamforces I went to before the pandemic and then the ones after with a bit of sadness.
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.
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.
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.
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*
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.
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.
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.
What We've Both Become
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.
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.
But we've both lost something in the process.
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?
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?
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.
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.
You see, I was never supposed to be in tech, but it’s the path that has shaped me, perhaps as much as the army did.
The Next Generation
Here's what keeps me up at night: How will the next Matt Pieper find their way into this world?
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.
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.
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.
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?
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.
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.
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.
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.
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’m more than happy to have: Right Sized Tech.
What has your journey been? Where will it take you next?
*Well, not me, as a street photographer, I travel incognito. If I look like I’m a conference attendee, I’ve done something wrong.