Our virtuous cycle: when operators do venture

I had ulterior motives for starting Operator Collective back in 2018. 

Sure, the core idea was always to bring together as limited partners (LPs) active operators from diverse backgrounds who had built the world’s most admired companies. They have the very expertise founders need as they grow and scale their companies, and the most relevant contacts with both potential customers and future employees.

They also bring their operating talent and outsider perspectives to shake up the venture world. After all, what operators do best when they see a problem is come up with a solution, and then execute the hell out of it.

Even though these incredibly talented executives are critical to the success of startups, they have largely been left out of the venture world. Traditional venture is rigid, competitive, and not team-oriented. It’s just not friendly nor particularly appealing to operators—especially in the case of our Operator LPs, 90% of whom are women and 40% people of color. The doors to venture have long been inaccessible to people from underrepresented groups.

Leyla Seka has always called herself an accidental venture capitalist. She first joined Operator Collective as a founding LP while still an EVP at Salesforce. She famously built and scaled the AppExchange, launching thousands of startups along the way, and was the first to champion equal pay, setting off the wave across the tech industry and beyond. After leaving Salesforce, Leyla was considering CEO positions as her next move. When I asked whether she’d be open to help build Operator Collective, I’m grateful she agreed to come on board.

Operator Collective was created, among other things, to serve as an anchor for active operators at the top of their game to engage in venture in a way that is collaborative and flexible, with aligned incentives. A place where they could not only continue to operate or ponder their next career move, but contribute to what we’re building, deepen their investing acumen, and have a supportive community of operators. Oh and have fun along the way.

Enter the virtuous cycle. I share with mixed emotions that Leyla is returning to a full-time operating position as COO of Ironclad.

She’s also transitioning to a new Operator Collective role as Chair of our Board of Advisors. Leyla joins Erica Ruliffson Schultz, Stacy Brown-Philpot, Claire Hughes Johnson, Tekedra Mawakana, and our newest Board member, Elena Gomez (welcome Elena!). I’m thrilled Leyla will remain a close part of the Operator Collective community, leading this group as they advise me, Operator Collective, and our portfolio founders.

Our model was designed to include active, current operators. Operator Collective and the venture world are better off today because Leyla Seka brought her operator lens to all that she learned about venture, and then ran with that knowledge to create a better ecosystem. Her substantial understanding of the enterprise software world helped Operator Collective make better investing decisions, and she leveraged her years of experience advising AppExchange startups to support our portfolio founders on how to scale.

One of these companies, of course, is Ironclad, which has built an extraordinary and beloved digital contracting platform. Working closely together for almost three years, Leyla and CEO Jason Boehmig very quickly developed a special bond, and it became apparent that she was uniquely situated to vault Ironclad forward in a way no one else could. Closing the loop on our virtuous cycle, Leyla is returning to her operator roots as Ironclad’s COO.

She has already made a huge impact on the industry, and she’s just getting started. Her relationships, outsider’s view, and execution also led her to create a long-lasting and game-changing institution called the Black Venture Institute, with a goal to increase the number of Black checkwriters in venture. This curriculum-based program has graduated 100+ fellows, including eight Operator LPs to date.

Leyla, my friend, I couldn’t be more grateful for all that you’ve contributed to building the heart, soul, and engine that is Operator Collective. Nor could I be more proud of how you took on the venture world and made lasting change during your time as an accidental venture capitalist. I can’t wait to see what you do next and am excited to be right by your side as you keep shaking it up.