I had a great job as Director of Sales running a 175 person sales team for a Fortune 1000 technology company.
I had a lot of autonomy. I was learning new things every day. In 18 months my team grew from 55 people to 175 people while absolutely crushing our sales numbers.
The people I worked with were mostly super-energetic, enthusiastic, driven millennials.
Although we were part of a large public company, our offices and our business were shielded from most of the bureaucratic BS that pervaded the rest of the company.
My boss was a maverick. His boss led the division and ran it like a startup.
It was pretty great.
Then I quit.
Why I Left
#1 I wanted to be part of a startup.
When I joined, our division had 100 people. I knew every person on the team and spoke with them regularly. We solved problems, pulled together and kicked ass.
By the time I left, our division had grown to 500 people. I had employees I didn’t recognize, managers who I could only meet with once a month and a dedicated HR person who had been assigned to “reign us in”.
Our parent company also announced plans to double in size. They hired C-level execs from other huge corporations to implement standards, procedures and cost controls to get us there (yuck).
#2 My boss was a crazy workaholic.
I reported to a guy who was kind of a cult leader. He did a phenomenal job of creating a culture of hustle, aggressiveness and no BS. He genuinely cared about developing and challenging people.
The downside was that he had no life, worked all the time and expected the same from everyone.
Reps worked 10 hours a day, plus had mandatory training during “non-calling hours” and on weekends. We paid for dinner every night so that reps would stay late making calls. We had work events continuously – happy hours, dinners, breakfasts and parties.
It was a fun, intoxicating environment for kids who were just out of college. It was like a continuation of campus life – except you made good money.
Managers had to do reporting, admin work and meetings during off hours – including weekends. We were expected to answer email and calls 24×7.
But for me, it was killing me. I had a wife, family, pets and a life outside of work that was sorely neglected.
#3 The money.
I was offered the position with a specific level and comp plan. Before my first paycheck (but after I had relocated) my boss said he made a mistake and had to bring me in at a lower title and comp. I was not happy about that.
But since we crushed our numbers consistently, my commissions helped make up for the discrepancy. However, my boss also raised our quota every month. If we were doing well, he’d raise quota in the middle of a month!
He often said that he didn’t care about money because his stock from the acquisition enabled him to never need to work again. But I wasn’t part of the acquisition. I wanted to maximize my earnings so I could retire someday.
I was regularly being contacted by recruiters offering me higher pay, stock options and VP roles. Although I wasn’t actively looking to leave, the offers were eye-opening. I was being seriously underpaid.
One day a recruiter called me about a VP of Sales role for an out of town startup.
He said I wouldn’t have to relo. They would open a satellite sales office where I lived that I would run autonomously. He told me about the founders who had started 2 other companies and sold them for hundreds of millions. This was their 3rd company.
It was small but well-funded, on an upward trajectory and doubling in size (or so I was told).
I interviewed and was offered the job with a significant pay raise plus stock options.
The rest is history.
I took the startup job. It didn’t work out the way I anticipated. My new company never opened the satellite office. Instead there was a company wide layoff just weeks after I’d joined.
I survived, but the company never did take off. Our technology was suspect, the demand was nonexistent, and the expectations unrealistic. Sales was a revolving door of reps and executives.
The compensation was decent but the stock options never paid off.
It wasn’t all bad.
- Taking this job enabled me to work from home for 2.5 years and eventually relocate back to Florida.
- The money I made moved me closer to early retirement.
- I got my life back because this company didn’t work at the breakneck pace that my previous employer required.
I also learned some very valuable lessons about my ego, venture funding, and reality vs. recruiting promises.
What happened to the company and people I left behind.
As expected, the company continued to grow and big corporate slowly permeated the culture.
Many of my former employees stayed – which I found surprising since they’d all professed a love for the “startup culture and freedom” and disdain for big corporate. I suspect the money was too good to walk away from.
Some moved on to other startups. Others took bigger roles for other companies in the area.
It’s good to see them do well. Occasionally, we catch up. Sometimes I even get to help them in their new roles.
My only regret in leaving the company were the people I left behind*
The absolute best part of the job was the people. There were lots of good people.
We gave a lot of people their first chance at a career. We hired others who needed a 2nd chance. Seeing them do well was gratifying.
I loved mentoring people and had plenty of opportunities to do it there.
It was great to be part of a team that really pulled together to do the right thing with such enthusiasm and energy.
I’ve been part of a team like this a few times during my career. It was pretty freaking awesome.
Now that I’m consulting part-time, I miss this.
But not enough to want to go back.
*And the 401K match. I missed that too.