Catching up with Pitchfest winner Ben Brooks of Pilot

Six months ago, the HR technology community was preparing to make its annual pilgrimage to Las Vegas for the HR Technology Conference & Exposition®. And CEO and founder Ben Brooks of Pilot was polishing his pitch for Pitchfest.

That’s the annual competition for startups, where 30 companies pitch their products in a fast-paced competition in hopes of winning thousands of dollars in prize money. Brooks and his company’s coaching platform walked away with the prize—and an oversized check for $25,000 that Brooks wrangled through the casinos and airport to take home to New York.

A lot has changed since then. But even before coronavirus upended so much about work and life, we wanted to catch up with Brooks to find out what the Pitchfest win meant to him and to his business. He sat down with us via video chat recently. Here’s part of our conversation, which has been lightly edited.

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Check back later this year for more, including tips for would-be Pitchfest winners for 2020.

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Brooks: I’m in Manhattan, and this is late March and usually it’s a beautiful time, but I’m inside my apartment. I’m used to working from home, our entire company is a remote company, but it’s still a lot more Zoom calls and things like that. So much in the world has changed. It’s a very different context than Pitchfest last fall.

HRE: Tell me a little bit about Pilot and how you got started.

Brooks: Pilot is an employee coaching software product. So we take what’s great about one-on-one coaching, which can change people’s lives, but only 1% of employees ever get it in their entire career. And we made it affordable and accessible by putting it through software so people interact. It’s a fusion of some live group video coaching and then weekly coaching activities through software.

HRE: What did the competition mean to you, to your team and to the company?

Brooks: It was really a great experience. We wanted to do well, which was to have a good pitch. It wasn’t about winning and frankly if we had not come away with a check or the prize money, it would have been completely worth doing because of the experience and what we learned.

HRE: And what did you do with the money?

Brooks: It’s $25,000 (and) in a small business that can go a long way, but it just had us go a little bit faster on the things we had in our roadmap, it helped us increase hours for some people we have on contract part time freelance we increase their hours. And it allowed us to accelerate our roadmap and launch some new features. And really we moved (faster with) some of our product feedback and enhancements. We listen to our customers, we interact with them every day, every week through text and email and live sessions and calls. And so, it allowed us to move to this new accelerated coaching product, which is what the market was asking for. So the prize money was able to help us get there faster. And we’ve been kicking off since January with that accelerated coaching program.

HRE: What did you learn from the competition process?

Brooks: For those who don’t know Pitchfest, you have a three-minute presentation and then two minutes of Q&A from the judges and in the final round, you have five minutes of presentation and three minutes of Q&A. That is a very short period of time. (By comparison) when we do a briefing, we have multiple calls in our sales process and the briefing on the products is an hour long.

So three minutes. That really stretched our thinking about what’s the right level of detail; what’s the right message; what’s the right sequence and density of things on our slides; how do we show the product, even though we’re not in a demo kind of environment; how do we speak to a broad audience that may not be technical about coaching or even talent development?

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We got an education through the process in and of itself, and the judges’ feedback and their questions, and the judges were willing to talk to us afterwards too. They were very generous. So it really helped us hone the message because we’re so passionate. I think every startup there is an expert at what they do, whether it’s a chatbot or it’s a recruiting thing or it’s an AI thing or whatever it may be. But we have to say, hey, we don’t need to explain the sun (when) you just want to know what time it is. And that’s the thing about getting our messaging really be spot on.


Check back with later this year for tips for success from Brooks.

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Elizabeth Clarke
Elizabeth Clarke is executive editor of Human Resource Executive. She earned a journalism degree from the University of Florida and then spent more than 25 years as a reporter and editor in South Florida before joining HRE. Elizabeth lives with her family in Palm Beach County. She can be reached at