How to Capture the Attention of Four Venture Capitalists with One Five-Minute Pitch

My conversation with the winners of the $50k Dreampitch competition

Anyone who’s tried to get a startup off the ground knows how important it is to take advantage of each and every opportunity to sell others on your vision. And when you have five minutes to share that vision in front of a crowd and four well-known venture capitalist judges for a chance at $50,000 dollars in funding — well, that’s what one might consider a golden opportunity. So, how do you make every second count?

Meet Ted Brown and Jonathan Crossman, co-founders of Digital Onboarding and winners of this year’s Dreampitch competition at TrailheaDX. After the judges’ decision was announced (and Ted and Jonathan had been handed their giant, $50,000 check), I had the opportunity to sit down with AppExchange EVP Leyla Seka and our Dreampitch winners to learn more about how Digital Onboarding got its start, why they changed directions with their vision and story — and how they turned it all into one prize-winning pitch. Check out our full conversation below.

Ted Brown, CEO and Founder, has a background in sales and an exit with a VC funded company under his belt. He’s a husband, a father to one black lab, and an American lawn sports enthusiast.
Jonathan Crossman, CTO and Founder, is a 15-year seasoned full-stack developer — as well as a husband, a father to two boys, a multi-instrumentalist, and a hobbyist woodworker.

How did Digital Onboarding get it’s start? How did you come together around this idea?

Ted Brown: “We both had an entrepreneurial spirit, I think, and met through a mutual friend. Two years ago, we quit our jobs and actually originally started the business on a different concept, which was more based on what we thought the problems were. But then we stopped talking, started listening, and heard loudly and clearly that new customer onboarding and activation was a major problem at every bank. And that just happened to match up very well with my background, in terms of the relationships that I had with banks, and I understood the problem very well.”

Jonathan Crossman: “I was actually in edtech before this, but the problems that we were dealing with were very similar. It was all about education, and figuring how do to deliver information in a uniform way that’s easy to digest, and then analyze, track, and improve on that. So I was in a different space but solving a very similar problem.”

That’s interesting, that you started out going in a different direction. What did Digital Onboarding do initially?

TB: “We were building a sales enablement product. We have great users who love the product, but there were just plenty of signs that we weren’t heading in the right direction. I believe the biggest problem was that top decision makers weren’t losing sleep over the problem. Lower- level people within the organization — sales operations, content managers, the sales people themselves — can love a product, but if the C-suite isn’t losing sleep, you’re not going to get budget for it and you’re just going to continue to push a rock up a hill. So it’s not that we weren’t solving a problem, or that we didn’t have a great product, but the C-level executives weren’t there yet.”

TB: “So that’s the category we were in and why we shifted spaces — because now, we’re not only taking on a big problem, but importantly, the problem is recognized by the right people. The C-level executives at banks and credit unions in this country are trying to solve this problem, and they’re losing sleep over it. The regulators have started noticing that all of these accounts that they’re calling ‘customers’ are not actually customers, so it’s getting attention. And there’s no one currently doing a good job of solving for it, but there are people looking for an answer.”

What made you realize that you needed to shift directions?

TB: “We started listening. Earlier this year, we met with the CIO and the Head of Member Services at Digital Credit Union, and they saw the product we were building and said, ‘This is perfect. Our top strategic priority is to do a better job onboarding members — if you can do a good job of that, every bank and credit union in the country would buy it.’”

TB: “So, we shifted to a new, totally different pitch. We’re still the same product — there was very little that we needed to shift from our roadmap, actually — but we changed the messaging, changed the target audience, changed everything about the story to an entirely different pitch. And the pitch is what won Dreampitch.”

Well that’s great validation — especially considering you just shifted direction earlier this year! What did you find to be the most difficult thing about the process leading up to Dreampitch?

TB: “The biggest challenge was writing out a short pitch. I have a tendency to get too far into the weeds, into the numbers and data, and I want to explain everything about the product. So the real challenge was reigning that in, and being higher level and less in the weeds for a five-minute pitch.”

Did you find the exercise of condensing your pitch to be helpful?

TB: “It was really helpful. Just in the process of continually getting feedback from people, you get a feel for what people react to, and it’s not always what you expected would be the thing that would get someone to nod his or her head. But you do it enough times, and then you put together all of the ‘hits’ — all of the times that you’ve said something and the person has reacted with ‘ah that’s a good point’ — and you condense those moments into a five-minute pitch. And that worked well for us.”

Who were you pitching this to in order to get that feedback? Who did you practice on?

TB: “A couple of angel investors in the Boston area — they’ve all been really helpful and willing to make introductions for us. And that practice was really important. You hear enough questions that you get better and better at addressing them concisely, and knowing what the objections are going to be. So every question that the judges asked, I’ve been asked before. And the first time I responded to those questions, I did a bad job. But you answer them again and again, and you get better at it. So it was a lot of meetings to find the right content; finding the right people to give good, credible feedback, and then just a ton of practicing on our own over and over.”

JC: “Practicing, and shaving off valuable seconds wherever we could. We didn’t want the buzzer to end our pitch.”

Did you find it difficult to tell your story without showing the product?

TB: “My personal preference is demoing the product; I like those kinds of pitches where it’s very focused on the product. But I will say, for this pitch I think it worked out a lot better in this format. Because what’s really exciting about what we’re doing here is the opportunity. The opportunity is a bigger part of the pitch than the product itself, because it’s a big problem. When you have a big problem that people can relate to, you use it.”

Another thing that you used in your pitch — which one of the judges, Josh , commented on specifically — was a prop. At what point did you decide to make that part of telling your story?

TB: “That was a starting point for this pitch. I knew from the start that I was going to have a prop, that I was going to physically bring in one of those bank welcome packets. So I called up one of the banks that we’re working with and asked if I could get one of their welcome kits and they said ‘sure.’”

JC: “I think it just helped illustrate the problem so quickly and easily. This glossy, $14 welcome package is supposed to entice you to download a mobile app — but they’re completely different mediums. It’s a total disconnect from what it’s trying to accomplish.”

What was the biggest thing you got out of Dreampitch?

TB: “We’ve had a lot of validation on this new direction, and winning Dreampitch is exciting because it’s the right kind of validation. We started in another direction, and we had plenty of people validating it but they were kind of false signals. The types of validation that we’re getting with this new concept are much more real, indicating that we’re heading in the right direction, solving a big problem, and getting into a big market.”

JC: “When we pivoted we definitely got even more excited about what we’re doing. And the more we show it off, and now with winning Dreampitch — it’s that extra validation that lets us know we’re not getting so focused on our own ideas that we’re pursuing the wrong thing.”

What’s next for Digital Onboarding?

TB: “[Dreampitch] actually came at perfect timing for our go-to market plan. Our first financial institution go-live is in July and our initial distribution partner resellers, Geezeo, will be doing webinar campaigns to their client base. Also, DCU is promoting us and showcasing the product to the other 26 credit unions they’re partnered with, and those are some of the top credit unions in the country; definitely ones we want to do business with. With credit unions, I find, the thing they value most is recommendations from other credit unions — they’re very cooperative. So we’re really excited about this. The sales cycles are a little slower, but we expect to be generating a lot of pipeline with this go-to-market plan, and in the next 3 to 12 months, those contracts will come in — and it’s off to the races.”


Miss out on all the action? Check out the recording below to see Ted and Jonathan’s full pitch.