Case Study: Jennifer Henderson | CEO at TiLT

This is a story about a founder who learned the “Investor Pitch as Story” model (IPAS) from Day 1 of her pitch journey – and how the opportunities, wins, and checks began to accumulate.

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.

This is a story about how and why the Investor Pitch as Story model worked for Jennifer and so many other founders who have it under their belts. Founders who learn it, master it, and Nail It? They stand a much higher chance of getting the funding they need – and sooner.

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.
UNC Monfort Challenge

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 IPAS?

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 IPAS, 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.”

Cindy provides expert public speaking coaching and brand consulting to entrepreneurs and small businesses who seek to master their message on stage, online and in publications. Her passion for crafting, analyzing and presenting messages developed through over 25 years in the corporate, academic and entrepreneurial worlds. 

Cindy coaches clients – 1-to-1 and in workshop format for teams – on pitch decks, TED talks, storytelling, presentation presence, brand messaging, PR strategy and more. Contact Cindy at or call 970-290-4684.

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“Last year, I reached out to Cindy to help me with a sales deck I use frequently. I learned how to personalize my presentation in an authentic and informative way, making it more interesting to deliver and for my audience to observe!  Cindy was professional, enthusiastic, and knowledgeable and her suggestions were spot on.  If you want to enhance your communication skills, gain confidence in speaking, and improve overall delivery, I definitely recommend working with On Point!”

Nicole Steed, Global Account Manager | Helms Briscoe

“The On Point ‘Investor Pitch as Story’ online course was a great fit because of my heavy travel schedule. It gave me flexibility as a student to learn and connect with Cindy as necessary. The videos and homework helped me to prepare strong, compelling presentations for potential customers (coaches, directors, school districts) and becoming investor ready.”

Justin Fleming | CEO at MyPerforma

“Cindy, Your coaching was fantastic. You are so good at this. I have done a lot of this too, but I am in awe of your approach, the simplicity of your suggestions and your general professionalism. Thank you.”

Susan Strong, Director at SAGE Boulder

Cindy was selected to present at the Career Thought Leader Conference in Denver. I attended her session and was impressed with her presentation and content marketing expertise. I have been a trainer for over 20 years and her presentation added specific impactful strategies that I will include in my next training. Cindy has a natural engaging style that is persuasive and professional. I would highly recommend working with her if you are looking to increase your business presentations.

Beth Kennedy, Executive Coach

You are a wonderful presenter Cindy! I have taken so much from your presentation at the conference. I noticed when you speak, you at times lowered your volume in a way where we still heard you, but it PULLED the audience in, as if you were confiding in us.

Your vocal variety was lovely, (as well as your content, of course!). The advice to gather your stories from your past and weave them into your presentations is spot on.

Julie Roberts, Linked In profile writer|Coach