Bootstrapping a Tech Company by an English Major: Kevin Groome, Founder of Pica9 (Part 7)

Sramana Mitra: I’d like to cover this CEO transition, which is always a tricky thing to do. For founders to let go and bring on a new CEO is a tricky transition. How did you do it? What wisdom do you have to offer for people who are trying to do that?

Kevin Groome: Let go of the suspicion that you’re irrelevant. For so many years, I felt like Pica9 was my fourth child and the most troubling of them all. Letting go of that and letting the organization stand on its own two feet can’t happen if I’m constantly doubting itself. Trust is huge – the trust in the whole organization.

I turned to writing about this industry and this category. It turns out that those are actually valuable insights not just for customers but for the crew too. That’s a way of continuing to have that influence without interfering. I didn’t do this perfectly.

There were periods when I was suspicious and I did meddle. I needed to discipline myself. The Board really helped because they didn’t get draconian about it. John would take me aside and try to point out where I was lacking a little bit in self-awareness. That’s another point I would bring up.

You don’t realize your impact. You think of yourself as just another person, but to the crew, you’re not just another person. You’re the founder. The smallest thing you do or say will have an outsized impact. Try to be aware of that and tread lightly.

The other point is that when there is something that needs to be said, close the doors in the Board room where you can have a candid conversation. In those times, don’t leave anything unsaid. That’s the time to lean in. If I didn’t speak honestly, it would come out in my behavior rather than in my words. I’m much better in words than behavior.

Today I feel like we’ve hit a really nice balance. I’m involved with some of our key customers. I’m having an influence on product direction from a distance away. That bodes well for the management team and the customers. 

Sramana Mitra: Your experience is very different from my experience. I ended up hiring someone to replace me – somebody not trustworthy. That made all the difference.

Kevin Groome: It’s not going to work if the trust is not there.

Sramana Mitra: This is what makes it a tricky situation. Human character is very difficult to judge in an interview. 

Kevin Groome: In many ways, my background made it difficult to scale a SaaS company. I come at it from a services background and from a non-technology background. When you hear “You can’t scale,” that can be really damaging. I certainly went through that. 

Sramana Mitra: You have to have rock-solid self-esteem to be able to plod through all that external noise.

Kevin Groome: Because I’ve stuck with it, I think we’ve reached a happy place. It may well be that I should just exit completely. But right now, we seem to have struck a really interesting balance. We’re climbing to $10 million. I just want to make sure that I keep that in mind. That’s 18 years of work. 

Sramana Mitra: You have to make sure that somebody doesn’t drive that to the ground.

Kevin Groome: That’s right.

Sramana Mitra: How big is the organization?

Kevin Groome: Our staff is 39 including an offshore development team, and we’re on our way to $10 million.

Sramana Mitra: I enjoyed your story. Thank you for your time.

This segment is part 7 in the series : Bootstrapping a Tech Company by an English Major: Kevin Groome, Founder of Pica9
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