My Last Day At PivotDesk

David and I have decided that it’s time I leave PivotDesk.  This has been the hardest choice of my professional life.

I wrote the team at PivotDesk a few days ago and stopped by the office to wish everyone well.   We have made commerical real estate more efficient and cost effective for everyone from entrepreneurs to small business owners to brokers and I’m extremely proud of that.

Hopefully this post helps others avoid a similar situation in their companies and gives some context on how this can happen to the best of teams.  As several mentors and incredible friends have told me, this is way more common than people realize.

Alright (sigh), now that’s out of the way so let’s talk about what the hell happened.

Over the past six months I gradually lost the confidence of my teammates.

Here’s how it happened.

Tunnel Vision
For the past three years I’ve woken up in the morning thinking about how to grow PivotDesk and fallen asleep almost every night thinking about what else I should have done that day.  At the park with my kids I was always reviewing my task list, on the weekends I’d crave time alone so I could think about what’s coming up, everything was about growth, scale, more.

I was so caught up in this type of thinking for so long that I had blinded myself to all of the other things that make a team truly work well together.  As all teams do, we’ve had a few disagreements over a variety of situations.  I handled these situations with little care, love or respect for my teammates.  I just wanted it over so we could go back to growth, scale, more.  Little did I realize, I was slowly eroding the support from my team that is needed to succeed together.  And worse, I was growing defensive and outwardly frustrated as my stress level rose.

Stuggling With Co-founder Balance
I began as VPE at PivotDesk and after our MVP and Engineering team took shape moved to VP of Product where I’ve been for the past two years.  I also have a second job as Co-founder.  This job has no job description or performance metrics, rather it’s a mix of a zillion different things from sales to ops to bizdev to customer support.  Finding the balance between these two roles has not been easy and is another reason I ultimately lost the team’s support.

Just a few examples:

• Taking coffee meetings instead of attending daily standup.
• Running the company meeting instead of focusing on a great product update during that company meeting.
• Letting my week fill up with sales, finance, pr and exec team meetings and not leaving myself enough time for deep product focus.

As I asked others on my team for feedback once I realized things were going sideways I heard things like “No one really knows what you do anymore.”

Making the Hard Decision
Saying “hard decision” doesn’t even come close.  When David and I talked about the possibility of me leaving I started visibly shaking, my mouth turned dry and I started having trouble breathing.  As the words “If I’m getting in the way at all, we should seriously consider that I unhook from PivotDesk” came out of my mouth it was surreal.  All of the emotions started kicking in; the Imposter syndrome, anger, disbelief.  We decided to give it a week, talk to the people that have seen this the most, then regroup and make a decision.  For a week I let all of the “Co-founder projects” slip and focused only on product.  I felt like our team was in perfect harmony and kicking ass.  We released a major feature and were collaborating perfectly on the next feature.   Our OKRs were lining up to our analytics informing what we were building and planning on our roadmap.  Ironically, it was one of my favorite weeks of work ever in my career.

At the end of the week David and I spoke again, there was no change in the team’s support, it was time to unhook.  I was crushed.

When talking with a good friend and mentor of mine this week he said “You are not special!”  As I laughed and said, “Hey, thanks a lot.  Is that supposed to make me feel better.”  He said yes and went on to talk about seeing this happen in different ways over and over in fast growing startups.  The company changes so fast and sometimes people and teams simply aren’t the right fit for the phase of the business anymore.  This did make me feel better and he encouraged me to not assume 100% of the burden.

The Next Chapter
It’s incredible how much of one’s identity can get wrapped up in the company they are trying to build.  The constant pitching, the t-shirt wardrobe peppered with company logos and talking about the business at every holiday, lunch with friends or phone call with Mom really adds up.  It’s what you live and breathe as a startup founder and I wouldn’t have had it any other way.

For me, one thing has always stayed constant over the past 20 years of my professional life whether working at a big company or startup, the love of building software.  From the first 10 years as a software engineer through today as a product guy, day-dreaming about cool ideas and turning them into reality is thrilling.  I still get nervous as a I watch customers, friends and teammates use the products I’ve help build.

I don’t know exactly how the next chapter reads, but I’m positive using PivotDesk to share office space will be a part of the mix.