This is a story about a founder who learned the Forbes.com featured HOW-TO model we developed from Day 1 of her pitch journey. It’s about and how the opportunities, wins, and checks began to accumulate when she gained mastery of it and implemented it again and again.
Jen wrote her first company check to On Point. It felt like a gamble. Would it be worth it? She admits in the interview… “it was a hard check to write.” Now that she’s mastered this model, she has investors writing checks to fund TiLT (formerly Career Allies) into its next phase of growth.
The latest? TiLT just scored $7.4 Million from a Series A raise.
I recently sat down with Jennifer, and this is her Story.
Q: How did you find out about On Point?
A: The first time I encountered On Point was at Ft. Collins Startup Week when you spoke about the power of the pitch in conjunction with the funding journey. That was compelling to me. I remember walking away with the realization that it’s 75% if not 80% about story – the story of the company, my story. I certainly got the point that communicating that was going to be critical, and that’s when I reached out to you for that initial pitch help.
Q: Where was your business when you thought about hiring On Point?
A: The company at that time was pre-revenue. It was just an idea, and we hadn’t even done our first pilot. I had done some market research and created some analog versions of the tool. Then you helped me put together that first pitch to 1 Million Cups.
After that came Longmont Startup Week and then the pitching just snowballed. I pitched at SAGE, Sim Tank, Boulder Seed Angel Forum, Morgan Stanley, Rockies Venture Club, placed 1st at Pitch NOCO and 3rd at the UNC Monfort Challenge, and there were many others. Then we got into investor audiences. That initial pitch we did has been built upon and built upon.
- Pitch Journey: 1 Million Cups, SAGE, SIM Tank, Boulder Seed Angel Forum, RVC Angel Capital Summit, Morgan Stanley, Fort Collins Pitch NOCO winner ($18,000 value), UNC Monfort Challenge (3rd place 7,000), Fightback Foundation, Global Workplace Wellness Summit (workshop), RVC road show. Tech Stars. Series A Raise, and much more in between.
Q: What was it like to write your first check to a consultant you hardly knew?
A: It was a cost benefit analysis. It was, ‘What funnel could I put these first dollars go into that would give me the largest ripple effect?’ Knowing after startup week just how long-reaching an effective pitch really is, it was very systematic in my mind. ‘Where am I going to get the biggest bang for my buck?’
“I hadn’t generated any revenue yet, so it was very hard to write that first check. Would I do it again? In a heartbeat. Because it has snowballed into so many more wins. It was a foundational investment. Especially interacting now with so many other founders who struggle in the communication of their ideas, they just don’t seem to understand how invaluable the investment in that early communication is.”
Q: Had you consulted other resources for how to build pitch decks, and if so, which ones?
A: “No. I remember building the pitch deck from scratch with you.”
Q: What made you say, “I need help with this. I don’t want to do it on my own.”
A: “I recognized this was a new space for me. As much as I had a lot of experience in my background standing up in front of a room and with my education in Speech Communication, this felt like a nuanced speech in that entrepreneurship is a different bag. You have to communicate different things to different people. So I had a self-confidence in how this pitch needed to be delivered and in what format, but I didn’t feel confident that I knew that format. It was out of my comfort zone.”
Q: Did you get feedback from people you knew after implementing the HOW-TO model?
A: “Yes. Whether winning or placing in pitch competitions, the majority of the time it resulted in some sort of win. And the majority of the time, people asked, ‘How did you get so good at your pitch?’”
Q: Let’s talk about the model. When you first learned it, did you get it right away, or did it take time to see it and study it?
A: The clarity came quickly. It was very easy to understand and also to apply. There are great examples you give that helped me put it into context quickly. It clicked right away. The back half of the model was the most challenging – the traction. But the story piece for my pitch – the front half – people have consistently loved that.
Q: Were there any pieces of the model that surprised you, or that suddenly seemed obvious after you learned it?
A: “The story arc. I was always told you need to grab people’s attention by grabbing them, by giving a staggering statistic or asking a question. But the building of story, hearing how people are wired for story, how big storytelling in business has become, that was a bit of an ‘oh yeah, of course’ moment.”
Q: Was the rhetorical triangle a helpful tool to learn?
A: “The rhetorical triangle piece definitely comes into play because every time I pitch I have to take into account the audience, which impacts the way I build the message, which impacts me the speaker and how I deliver it. Audiences can be very diverse, so crafting the message can be hard.”
Q: What would you tell other people about what it’s like to work with On Point?
A: “I will always remember when we first started working together. I was on vacation in Minnesota for a family event and you had given me some initial work to do, to sketch out the skeleton of my deck. And one of the things that really was enjoyable was the responsiveness. I’m always drawn to people who are responsive. I remember talking to you in my aunt’s office going back and forth, I think we did a zoom meeting. It was clear in the beginning what the expectations were, the timing, and you followed through on that and then over-delivered in regards to my understanding of the finished product.”
“And then – the icing on the top – was that you were there for my very first pitch in person. And there was in the moment real feedback which was so invaluable. It just meant a lot in terms of closing that loop. You’ve just always been there. And you just do all the extra things like, ‘Hey this might be a great opportunity for you’ or ‘hey I met this person that you might want to meet.'”
According to Forbes.com, Cindy Skalicky is “arguably America’s top expert in evaluating persuasion effectiveness.” She has helped company founders raise millions of dollars in venture capital. She has personally trained executives at Microsoft, members of the Young Presidents Organization (YPO), and countless entrepreneurs pitching deals to the investor clubs all over the United States on how to win multimillion-dollar deals.
Cindy helps speakers and teams Nail It. She coaches speakers and teams on A to Z presentation training, speech writing, delivery, and overall content development. Cindy also provides specialized workshops in Scientific Messaging and Executive Presence. Master the Message. Learn more at www.onpoint-communications.com or contact Cindy at: cindy@onpoint-communications.com.
Jennifer Henderson
BBB Spark Award
