Former Brightcove CMO Jeff Whatcott on the Road from CMO to CEO

Jeff Whatcott has worked at some of the software industry’s best-known and most innovative companies – Adobe, Acquia and Brightcove to name just a few. Now, as the co-founder and CEO of Outlearn, a publishing platform for professional developer learning, Jeff’s taking decades of marketing experience and applying it to his newest venture.

As a career marketer, most recently as the CMO of Brightcove, founding a company solely dedicated to developer education might seem like a counterintuitive leap. But for Whatcott, the move made complete sense.

“If you look back at my career, I’ve spent a lot of time with developer audiences. In fact, most of the tools and platforms I’ve worked on were either used by front or back-end developers,” says Whatcott.

“As a marketer and a product manager and really as a manager of technical evangelists, I spent a decade really focusing in on the needs of developers. And, while I’m not a developer myself, I felt like I understood the space. I felt like an anthropologist to developers. I spent a lot of time understanding their culture and how they work together,” he adds.

“After I left Brightcove and was looking for my next role, a VC friend asked for help looking at how edtech could be applied to the enterprise, which was just generally interesting to me. Together we started brainstorming different business ideas that made sense to form. Since we both had an interest in educational technology and developer ecosystems, we thought maybe there was something interesting at the intersection of the two.”

“It was very natural for me to go and talk to developers and people who manage developers, to ask them about their learning challenges and how important learning is overall to their culture and work. This research quickly revealed that there’s both a huge need for learning as well as a ton of challenges that developers experience as they try to learn. This all ultimately led me to start Outlearn.”

Transitioning from CMO to CEO

While it might have been counterintuitive for a career marketer to start a developer learning company, Whatcott’s experience as CMO has only helped in his newest role as CEO.

“The transition has gone quite well, but I’ve had to remember that my job now is less about marketing and more about sales” he says. “As a CEO you’re selling the concept of the company to investors, prospective customers – especially at the seed stage where you are the sales team – and you’re selling the company to the people you’re trying to hire.”

But more than his years of training could have ever provided, as CEO Whatcott has learned the importance of trusting his gut. “Especially in a small company in its very earliest stage, there are often cases where you don’t have a lot of data to analyze. You’re not really an operating business yet. You don’t have historical spreadsheets to look at. You don’t have a lot of people to talk to and synthesize their opinions. You have to be in a state where you can make decisions and move forward and assess your situation more on gut than at any other stage. I was lucky that this became clear to me in Outlearn’s earliest days and even luckier that we made it through.”

“This,” says Whatcott, “is something your business career in large organizations simply can’t prepare you for. That ability to make a decision with truly imperfect information and iterate from there is something I think that can only be learned from experiencing it.”

“You have to be willing to make decisions based on very little information and let your gut guide you,” says Whatcott. “But, at the same time, you have to also be willing to not get too wedded to any idea or concept and that can be challenging.”

This is the nature of the beast in any early-stage startup and perhaps something for which no one, regardless of their experience, can prepare.