The Pilot Advisory Program

Helping Founders become Executives

Jonathan Sherry
3 min readNov 17, 2020

The transition from founder to executive leader isn’t a subtle one. The founder’s job is to discover product-market fit. The executive’s job is to take product-market fit and turn it into something scalable and repeatable that ultimately grows up to become a company.

A lot has been written about what constitutes product-market fit, so I’m not going to cover that here. Although Pilot Growth has plenty of bootstrapped entrepreneurs in its portfolio who have successfully navigated product-market-fit, that’s not where we specialize. Rather, Pilot invests once product-market fit is achieved and the founder is ready to commit to the journey of scaling their organization.

And to be clear on the term “invest”, yes we offer capital. But that’s table stakes.

Rather, the unique leverage that Pilots offers is a full stack advisory program that addresses the patterns that all founders face when it comes to scaling both their business development and operations.

Business Development
Pilot’s advisors within business development are essentially human rolodexes.

Our business development advisors are typically quite seasoned in their careers, have achieved senior leadership positions in large organizations and/or government and command a huge network that they’re willing to call on in order to open doors for our portfolio companies. They’ll not only review the current pipeline, but also help generate new opportunities. While sometimes these advisors have startup experience, it’s not a must as the leverage they provide is the network, not the operating know-how. This role plays very well to potential portfolio companies who simply need to break through to the right buyers in large, black box enterprises.

Operations
Pilot’s advisors within operations are masters of their craft.

Our advisors within operations are current senior practitioners (VP+) with experience at companies operating in the zero to $50+ million revenue range. They are not Jack’s or Jill’s of all trades, but rather super focused on doing one thing and doing it extraordinarily well. Moreover, these advisors must be natural educators as the leverage they provide will be in teaching this craft to leaders within our portfolio companies. The operating disciplines Pilot offers include sales, customer success, marketing, human resources, product, engineering and finance. While coming with a network is nice to have, again these advisors are not the human rolodex but rather provide the true know-how in scaling a high growth business.

If you’re a Pilot company, you get ready access to these advisors. In fact, as a founder within Pilot’s portfolio, I’ve experienced it firsthand.

If you’re a founder or CEO who would like to learn more about Pilot’s advisory program, either drop me a line or sign up for Pilot’s newsletter, which includes feature pieces from our advisors as well as announcements of upcoming webinars like the one we did last month with successful serial entrepreneur and CEO coach, John Belizaire. Shoot me or Amy Lund a line if you’d like a recording of John’s session. And if you’re a potential advisor reading this post, Pilot is always looking to deepen our bench of experts so please be in touch.

For more stories like this one, sign up for The Sounding Line — a publication from Pilot Growth Equity offering facts, insights and opinions on growth equity in technology.

--

--

Jonathan Sherry

Founder / CEO, Alium (alium.io). Previously co-founder / COO CB Insights. Builder of things.