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There are many things I love about my job, but one of the most exciting aspects of running AppExchange is watching innovative new ideas evolve into businesses. And few things embody this mission (and expose the phenomenal amount of talent within our ecosystem) better than our Dreampitch competition.
So I was thrilled that we were able to bring Dreampitch to our TrailheaDX conference this year, giving three teams of finalists a chance to pitch their startup vision on the mainstage. And I was even more thrilled when we were able to secure a panel of rockstar venture capitalist judges, giving these teams a sense of what it’s really like to ask for money from experts who have heard countless ideas for new business ventures (and giving the audience a great show). If you missed all the action be sure to check out the full recording below, but after five minutes of pitching and five minutes of Q&A with the judges for each team, the judges gave their ratings. And the latest Dreampitch champion — and recipient of $50,000 in funding from Salesforce Ventures — is Digital Onboarding, a SaaS solution that helps banks onboard new customers and assist them with activating their financial services products.
I had the chance to chat with the two New England-based co-founders behind Digital Onboarding — CEO Ted Brown and CTO Jonathan Crossman — after the event (and between taking pictures with their giant, Appy-signed check). It was great to hear more about Digital Onboarding’s roots, why they changed directions a year into founding their company, and what they learned from setting out to write a prize-winning pitch — and our conversation got me thinking about some important lessons in pitch writing for hopeful startups everywhere.
The first step before you sit down to write a pitch is simple: listening. Don’t make the mistake of thinking you thoroughly understand the problem that needs to be solved (and have the knowledge required to write a resonating pitch) based solely on your own experiences. Our friends at Digital Onboarding, Ted and Jonathan, actually quit their respective jobs two years ago to start the business, but realized later that the problems they thought needed to be solved in financial services weren’t necessarily a priority in the wider industry. “So we stopped talking and started listening,” Ted said — excellent advice and critical first step to ensure you’re you’re not getting tunnel vision around your idea.
This brings me to my next point: Don’t be afraid to completely shift direction. It’s critical to keep an open mind, be ready to swallow your pride, and admit that your initial idea may not have been the best idea. In the case of our Dreampitch winner, they totally shifted direction a year into starting the business — as Ted put it, they “kept the product but changed the messaging, changed the target audience, changed everything about the story to an entirely different pitch.” A few months later, that pitch won them $50,000 in funding. Sometimes a reevaluation and change in direction can be the secret to kickstarting the growth your business.
Never lose sight of who is listening when you’re making a pitch. Your vision can be flawless, but it also has to matter to the person hearing it. The main reason that Digital Onboarding shifted direction, as Ted Told us, was the realization that the problem they were solving “wasn’t keeping executives up at night.” So even if the problem you’re solving for, say, a sales operations manager is very real and very painful, stop and think: Are you pitching to that sales operations manager? Or are you talking to their boss’ boss? If you’re talking to the C-suite, you have to find a way to translate that problem into something that’s top-of-mind for them. Make sure that you’re hitting hard and fast on what matters most to your listener — and, of course, speaking their language.
The first person to hear your pitch should never be the person you’re counting on to buy your product or provide funding. Our Digital Onboarding friends told us that they held multiple meetings with angel investors in the Boston area leading up to the event, and had already fielded all of the questions the judges ended up asking them multiple times. And, as Ted told us, “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.” Make sure you’re finding people who will give you the right kind of validation — asking you hard-hitting questions and giving you a chance to handle objections — and practicing on a number of those people before you get to the pitch that really counts.
We often hear from participants in our pitch competitions that the most difficult part of the whole process is shortening their pitch to meet time constraints. However, this is one of the most important exercises you can do as a startup. When you narrow down your pitch to the bare essentials, you get to the heart of why you do what you do, and the crux of what matters to your listener. The Digital Onboarding team practiced explaining their vision to multiple investors, taking note of the moments where they hit an ‘aha’ moment with their listener (“it’s not always what you expected would be the thing that would get someone to nod their head,” Ted said) and compiling those impactful moments into a more concise pitch. Then, as Jonathan told us, the team spent hours practicing and shaving off valuable seconds wherever they could —“we didn’t want the buzzer to end our pitch”— and cutting out extraneous details. And the result was a compact and memorable pitch that told the judges exactly what they needed to know (no more, no less) to pick the winner.
