11 Steps to a Great InsurTech Demo Day Pitch

11 Steps to a Great InsurTech Demo Day Pitch

May 11, 2018/ 0 Comments / / by Jim Gardner

So, you are off to an accelerator! Odds are, you will be pitching at Demo Day. The Pitch on Demo Day is a really big deal. If you don’t agree with that, then you should not be at the accelerator. Spending 3-4 months building your pitch is core to telling your company’s story. If you don’t have a compelling story, you will not have a company for long.

Lessons We Have Learned

Jay Kramer (our COO) and I have done 2 accelerators, 1 incubator, bunches of Shark Tanks and countless one-off pitches. This is what we have learned from these experiences, most recently from Insurtech Hartford.

Step 1: Start Before You Get There

You won’t get through selection without doing your pitch many times. We guarantee that on your first day at the accelerator, you will be pitching within the first 4 hours. Bring a well thought-out and polished pitch with you. Don’t be too attached to it. The folks at the accelerator will be intent on dismantling whatever you bring.

Step 2: Script First

At the Global Insurance Accelerator, it took us about 60 iterations on the PowerPoint before we learned that we should start with the script first! Sounds simple. The siren song of making cute PPT slides gets most of us at some point. When we started with the script first, our slide deck went from fuzzy to focused. A great resource for us has been Jennifer Rosen from FullTilt Communications. Her video on story telling is amazing.

Jen’s LinkedIn: https://www.linkedin.com/in/rosenjennifer/

Website: https://www.fulltiltproductions.co.uk/

Video Link: https://www.youtube.com/watch?v=9RUVrf32j6Q

InsurTech HartfordStep 3: The Black Box

In the 5 minutes or so that you will have for your pitch, it is tempting to vomit out everything you can squeeze in about your startup. You will lose your audience if you take that tack. We stopped doing that when we learned about the “Black Box.” At the pitch level, your audience has no interest in HOW you are doing what you do. They want to know what they get. What is in it for them? Save the details for later.

Step 4: Pro Grade PowerPoint

There are no excuses for amateur PowerPoint slides. Well, there are, but we used them all up! One of the cohorts at the Global Insurance Accelerator (GIA) came in with a deck built off from a ThemeForest purchased design pack. It was shockingly better than anything the rest of us had. He rode that deck out all the way thru the GIA, and no one ever challenged him to tweak it, it was that good looking. We are sure there are many options out there, but you cannot go wrong with:

Step 5: Quality Images

We like to start our pitch decks with ONLY images. No words. Then the focus is just on the quality of the image and what it is communicating. The text we add subsequently seems to come easier with this approach.

We spend hours on picking images. Truly. An hour for one image is not excessive to us.

We buy our images or use freely available pics from Pexels. My photo site of choice is Shutterstock and Jay’s is ThinkStock.

Pexels: https://www.pexels.com/

ShutterStock: https://www.shutterstock.com/home

ThinkStock: http://www.thinkstockphotos.com/

Step 6: Trim the Text

The biggest negatives we see in presentations is too much text. There is absolutely no way that the audience can listen to you AND at the same time, read deeply texted slides. Give them a great image and a few select words or a phrase.

Step 7: Lock It Down

You must protect yourself and decide when you are going to lock down the script and the PowerPoint. Otherwise, you will have people making suggestions and tweaks right up to Demo Day. At Startupbootcamp in Hartford, we locked down the script 4 weeks out. The PowerPoint took longer due to some designer issues. However, if we had known about ThemeForest or the like, we would have had the PPT locked in a month prior as well.

Jay and I have shared doing the pitches. By settling on your script and deck early, it lets the person pitching start SERIOUS practicing. Another trick we use is that whoever is pitching gets to make all final decisions on the script and deck. It must be in their voice!

Step 8: Practice

Professional speakers may have 2-3 current “talks” that they can give at any moment. This because they have practiced them and given them dozens of times. It has become part of their soul. We practice our pitch in the month leading up to Demo Day. At Startupbootcamp, one of the most effective methods we found was “pitches in a bar.” Distractions galore, no slides. Just you and your words. Beyond that, try these:

  • Pitch every day. To anyone. Anywhere.
  • Have people try and throw you off track with hand gestures, questions or interruptions.
  • Practice technical issues: No slides, Clicker dies, Video does not work, etc.
  • Plan for people to request you give surprise, off the cuff pitches. No warning.

Step 9: Smiles and Gesture

Jay has a great stage presence. It looks natural and draws in the audience. In the final few days prior to Demo Day, he was figuring out gestures, and we were reminding him to smile. Watch his video from Startupbootcamp, and I bet you can pick out the gestures he focused on!

Demo Day Video: https://youtu.be/Y7G-nHWMOpU

Step 10: The Night Before Demo Day

Nothing sucks more than the night before Demo Day. It seems as though we all totally blanked on what we were going to say, technology never goes right, and panic starts to set in. Never fear. Somehow it all seems to fall into place. Demo Day will be great but take full advantage of every moment on the stage to get comfortable.

Step 11: Lean on Your Mentors

In Jay’s video, David Bourque, one of our mentors from Startupbootcamp, does our introduction. David, who is a HubSpot Agency Partner, provided expert guidance on messaging and showed up week after week to simply knock ideas around. As our mentors, David, along with Frank Sentner were highly invested in our success, and we knew we always had some go to folks to reach out to.


So there you have it. As you can see, our focus is not on the standard slides of Demo Day (The Problem, The Solution, Your Competition, etc.). We have found that a memorable pitch is one which reflects a company that worked hard to refine their message and then boiled that message down to images which are supported by focused narrative. Good luck on your pitch!

Here is an infographic of my tips for a successful demo day; click below to download your free copy!

Download My Infographic


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