Goodbye, Procore

Working at Procore defined my career. I often reflect on whether the experience was good or bad—and the truth is, it was both. Ultimately I grew and learned many things about business, people, and myself.

Nestled on the bluffs of Carpinteria, Procore sat on some of the most prime real estate in the world. Just south of Santa Barbara, it overlooked the ocean and was within walking distance of the legendary surf spot, Rincon. It was the gem of Santa Barbara's growing tech scene with a $2B+ dollar valuation and rapid growth. At the time, I didn't realize just how much of an anomaly this was—or what it would mean for my career. So when I received the call in 2017 with my hiring offer, I didn't hesitate to say yes. I remember crying as I felt a weight lifting off of me. I'd had a very traumatic year and this was a break that I desperately needed. The struggle of working through my early career as a college drop-out was being rewarded with consistent income, benefits, and career growth. This brought me hope that I hadn't felt in years. From the bottom of my heart, thank you Procore.

The lifestyle was incredible. My breaks involved walks along the Pacific Ocean. I made friends with good people. I enjoyed free meals, lavish events, and a beer-stocked fridge. I sat next to a beautiful, witty, and inspiring woman, and I was there the day she brought her puppy to work for the first time. They quickly became a big part of my life. Having a dog to play with, walk, and babysit brought me back to my childhood and softened my heart. I finished most days snapping pictures of the blood-red sun as it sank heavy into the horizon.

However, my rose-tinted perspective didn't last long. I was quickly thrust into an entry level position of a large and dysfunctional marketing department. I joined one week after the incumbent CMO had been sacked, on a team with a long history of spotty leadership, under a manager who glorified getting paid to do nothing. And there was a lot to do.

Out of naivety, habit, and nature, I ignored the warning signs and dove deep into my work. I reveled in having the skills to solve challenges that needed solving. I didn't let my SEO Specialist I title define me—I touched everything I could, from web analytics to CRO to development. It was an outlet that filled my empty life. I was always the last one out and 60 hour weeks became my norm, my identity. I didn't have to work like this, most of my peers worked a relaxed 30-40 hour week, but I chose to. I truly loved it.

Over time, this naivety translated into frustration. It felt like no matter how hard I worked or how much I achieved, my efforts weren't recognized in compensation. I was well known, my reputation as a determined problem solver spread through the company. I received plenty of verbal praise but saw little actual career growth, especially when compared to peers who seemed to be receiving a promotion or raise with every cycle. In four years I received one promotion and a title change that moved me into web development.

I learned some very hard lessons about the reality of corporate politics and the importance of team structure. Underlying my experience was chaos. I experienced the regime change of three direct managers, four team directors, and two CMOs. Each with new expectations and no clue about what I had previously achieved. Further, Procore's "three O's" culture—ownership, optimism, and openness—was subverted into an Orwellian apparatus of control and performance theater. Directors would swoop in with a final review of my work to slap their name on it, exemplifying "ownership." My performance reviews would be dampened by the fuzzy critique that I "wasn't an optimistic team player." Meanwhile, I suffered the double-speak encouragement to be "open" about my career ambitions, so long as we never spoke about compensation. Salary negotiations were actively discouraged and veiled behind layers of red tape as managers were trained to suppress information.

Our unusual setting on the picturesque bluffs of Santa Barbara was a contributor to this inefficacy. We didn't have the talent density of Silicon Valley. The greater Santa Barbara area was only around 120,000 people, and the local colleges were acclaimed for their achievements in optics, not computer science. Leadership found it important to support the community and selected most of the first thousand employees from the sun-baked UCSB grads who lived there. These were happy-go-lucky, granola crunching, West coast surfers who were enamored by Procore's unlimited PTO and free lunches. Hard-nosed, contrarian obsessives like myself were considered "poor culture fits."

My peers who performed well in this environment were politically savvy and fortunately positioned. They knew how to play the game. They were often attractive, charismatic, or both. They embraced the culture and wore a smile while elaborating on why Procore was the best company to work for and how excited they were to make an impact. They were on small, stable, and visible teams who were vastly preferred by the team-based budgeting structure. Or, of course, they were opportunistic new hires who would be paid 50% more for the exact same position. Salary bands, by the way, were entirely defined by your starting salary—meaning it would've taken me a decade to reach the six-figure income many of my peers were already earning. And though the idea of department transfers was publicly touted as a possibility, my dream of transferring to engineering was never entertained with even an interview.

Being close to the numbers, I knew the ugly truth. 90% of the attributable revenue flowed through the team I was on. 60% flowed through my direct role in the form of search engine traffic. Of course, it was a team effort to generate this traffic. That would not have been possible without the incredible work of the many talented people who built Procore's brand. But, my team was collectively overworked and underpaid, despite producing real, measurable results. Meanwhile, I would watch as other team's campaigns would cost upwards of a hundred thousand dollars to produce less than a thousand visitors and yet they were celebrated and handsomely rewarded. It became abundantly clear that the department's incentives were deeply and chronically misaligned, so I quietly began planning my exit.

I owe a lot to the third manager I had while working at Procore. He truly valued my contributions and empathized with my unrepresentative compensation. He went to bat for me and secured me a generous equity award. Amortized over my four years, I still didn't break a six figure salary, but I am eternally grateful for him and he has remained a generous and loyal friend to this day. Despite this, it was too little, too late, and my motivation had withered. I stopped working 60-hour weeks and I waited as the last of my shares vested. I joined a coding bootcamp and materialized the career I had been chasing. I was an engineer—dammit.

Ultimately, I am responsible for my lack of success at Procore. My inexperience, my eagerness, and my distaste for politics left me woefully unprepared for corporate realities. This would've been true at nearly any company. And in the end, I grew. Watching a company triple in size over four years and exit through an IPO exposed me to invaluable experiences. Learning to evaluate a department's efficacy and seeing how structural misalignment results in poor incentives are skills that I will carry throughout my career.

It was frustrating. It was exciting. It was fun. It was real. It molded me and awoke a deep desire I had long nurtured. I am meant to be a founder. I am not like most people and this is my strength. I have a broad technical skill set, insatiable curiosity, unusual risk tolerance, and an unreasonable streak of individualism—along with indefatigable determination. Since leaving Procore, I have found immense pleasure in founding my own companies and finding my own work. This has been a period of enormous personal growth. I am more comfortable, happy, and grounded than I have ever been. My life is full now. The insecurity that underlay so many of my interpersonal deficiencies is slowly fading. My goal is to build an asset that earns me money while I sleep. Once I achieve this, I can dedicate my time towards building and sharing the knowledge of how others can do the same.

Goodbye, Procore. Thank you for shaping me into who I am, for giving an unusual, inexperienced young man a front-row seat to the chaotic reality of hypergrowth. It awoke something in me that will never fade.