CareSpotter’s Founder Shares 8 Secrets for Perfecting Your Pitch

By Danielle Davis


My all-time favorite pitch has to be by Darren Wendroff of CareSpotter. His Innovation Day pitch – the winning pitch from GuideWell’s first-ever Innovation Day in 2013 – stands out for a lot of reasons. It was well-crafted. The value proposition was clear. And Darren was an engaging presenter.

Darren approaches pitching like Payton Manning takes on football. He studies. Watches film. Films himself and dissects it. Has a fundamental process for developing his pitches that he practices over and over again. Darren doesn’t just have advice; he has a pitching philosophy.

Here’s the best of what other start-ups can learn from Darren, who, trust me, did his research.

1. Write out the entire pitch

“I start by writing out the whole thing,” explains Darren. “I have an outline in my head – a general idea of what I want to say – and I talk through it and write it down as I go.”

Hearing it out loud helps Darren build movement and flow into the story he’s telling; capturing it on paper means he can go back and refine things.

“What some people don’t realize is that a pitch should have a rhythm to it. Just like a song has a chorus, a beginning, and an end – a pitch should too. After I write it, then I go and read it back out loud again and again. I add punctuation. I erase things. I make sure it’s tight. You don’t want to waste words.”

2. Don’t be afraid to add details

Like Darren said, “erasing things” is usually a big part of the editing process. Anyone who’s gone through this knows – a lot of effort is put into deciding what to take out of the pitch. But Darren also offered the opposite advice, and taken together, it’s a good counter measure.

“One of the things I’ve learned is that if my pitch doesn’t feel right, that usually means I don’t have enough information in it. I need more details. It’s like when you get writer’s block – it’s because you know inherently that you need more information, more stats, more details.”

 3. Make your problem their problem – and do it right away

“What you want to do in your opening,” Darren explains, “is engage the audience as quick as possible. You want them on the edge of their seat, with all eyes on you…just wanting to hear what you have to say next.”

“I try to get them engaged in helping solve the problem we’re trying to solve.”

“I talk about why the problem is important right now. How long people have been trying to solve the problem. What makes this problem so important to solve. I give them numbers. Talk about families. I try to make it personal.”

During Healthbox, one of CareSpotter’s mentors, Mark Stryker, GuideWell Connect’s Chief Business Development Officer offered an idea for getting the audience’s attention more quickly.

“He suggested that I start the pitch with a question. ‘Just by a show of hands…how many of you have struggled with finding a caregiver or know someone who has?’”

“And EVERY TIME, at least two-thirds of the audience raises their hands.” Darren is excited even just recalling how well this has worked.

“That’s it! Now you can see the problem right there. It gives me a different soundbite to start out with. I can look around the room and say, ‘This is a real problem, it’s right here in this room, it’s your problem, and now we need to talk about how to fix it.’ 

4. Personal stories have to be a perfect fit

Personal anecdotes can also help engage the audience in understanding the challenge your company is taking on, but you need to pick your story carefully. It’s not enough for the story to be relatable, it also has to be extremely relevant to the product you’re pitching.

“If you’re going to use a personal story in your pitch, you have to make sure that it really fits the problem. You have to have a strong connection between the two.”

“It can actually make things worse when the story doesn’t have that connection because it can feel contrived. Some people pitch tragic personal stories or funny ones, but they don’t have to do with the product their pitching. The audience will pick up on that incongruence.”

 5. Save yourself the headache and time – research slide design

“It’s that old saying – ‘good artists create, great artists steal.’ So, I researched slide design. If you Google ‘pitch deck design,’ you’ll get so many ideas for how to make your slides. One of my favorites”

“The competitor slide, the revenue slide – everyone has to have these. So go see how others have presented them. It saves you time in coming up with ideas for how to present the information. Plus, you get a feel for how you can make yourself stand out when you see what everyone else is doing.”

6. Pictures – and failed live demos – speak 1000 words

Darren says he starts to develop his slides at about the same time that he’s writing out that first draft of his pitch. The key, though, is that the deck needs to follow the story – not the other way around. Your slides should add to what you’re saying by punctuating your words with visuals that add emotion or help convey data or information that’s too difficult to conceptualize.

“Images are really important because they convey feeling. I’ll search for images based on the words that are in my pitch. If I show charts, I make them move. Animate them. Whatever information you’re presenting, you want to present it in a captivating way in the slides.”

But a word of warning: “Just don’t ever demo live.”

“Use screen shots or do a video of the demo. In a live demo, you’re going to make mistakes, you’re bound to have equipment or website failures. Just click play and talk over the video instead. People will still see what you want them to see…it’s just not live. And they won’t even remember that the demo wasn’t live! But, they will remember if your site has a whole bunch of error messages.”

 7. Watch yourself.

You, as the presenter, are a critical part of your pitch. Lots of entrepreneurs forget this, and don’t work on their own role in the presentation.

For this, Darren suggests: “Video yourself practicing. You’re going to see things that you didn’t even realize you were doing.”

“The visual aspect of your presentation is half of your pitch. If you look calm and measured, people are going to perceive you as an expert.”

What specific types of things does Darren look for?

“When I watch myself, I’m looking for errors – little things. Inflection in my voice, little physical ticks that I do to calm myself down when I’m on stage. You want to minimize that.”

8. Watch others.

Really want to look like a pro? Then, study the pros. Darren doesn’t just critique his own films; he assesses other great presenters to see what he can incorporate in his own presentations.

“Before Innovation Day, I watched 30 or 40 different presentations. Ted Talks…Steve Jobs…Tech Stars Demo Day. Different lengths of presentations – ten minutes, two minutes…there are a ton of them on YouTube.”

“Looking at really great presenters, you learn a lot. It helps you figure out how to get the timing right and how to fine tune your own actions. ”

Darren’s big take-away: “OK, so, I’m Latin and I move my hands and arms a lot when I talk.”

“When I watched these other speakers, I saw that they controlled their movements so that they could create these visual cues that something important was coming in what they were about to say. For example, Bill Clinton would hold his hand this certain way whenever he wanted to make a point…”

He laughs and continues, “…So, I started making sure I didn’t move my arms during the presentation of our revenue model anymore.”

Where are they now

Since completing the Healthbox accelerator in October 2013, CareSpotter has helped match 648 families with caregivers through their online platform, and the company is in growth-mode.

They are currently developing a workplace caregiver program, and are actively seeking strategic referral partners – providers, physician groups, employers – who can help them introduce CareSpotter to the families who need it, at the time they need it most. Their service area is expanding to cover the entire state of Florida, and now a new strategic partnership will make it possible to launch the site in Australia.

CareSpotter was named the 2014 Central Florida Innovator of the Year by the Orlando Economic Development Center. As for Darren…he put his pitching skills to great use recently as a selected presenter at the 2015 AARP Life@50+ Expo this past May.


About the Author

Danielle Davis

Danielle Davis, MBA, works as an Innovation Consultant for GuideWell Innovation where she manages the relationship with partner Healthbox to run accelerators for entrepreneurs in the health industry. A financial whiz, Danielle is also actively involved in Waste Not Want Not, a local non-profit tackling hunger in her community. Connect with Danielle on LinkedIn or email her at