Selling is hard. Whether you’re selling an idea, service or product, you’ve got to get to the core of the issue quickly or you’ll lose your audience. And the challenge is notoriously exacerbated by the risky, regulated and complex healthcare system you’re selling into. That’s why we’re talking with Dom Cappuccilli from The Clean Sell. Dom’s a storyteller turned sales guy who’s been successful in both inside / direct sales and enterprise sales. Dom shares some of his most important lessons from the journey like:

  • How to avoid common sales mistakes like over-reliance on your deck
  • Why no-one cares about your solution and how to get to the core of their problem with needs alignment
  • How to use relevance hooks to earn the right to share more
  • Why you should always reach out to 5 or more people at a large organization (and no… they won’t get mad at you)

There’s much more too. At the end of the day, Dom shows us that these aren’t lame sales tricks to get what you want. No. They’re tried and true methods in human communication and relationships and you neglect them at your own peril.

This one was a lot of fun. Check it out!

P.S. Dom shared an awesome quote from one of his colleagues that’s worth pondering:

“People don’t buy from you because they love your product. They buy from you because they believe you understand their problems”. – Dom’s unidentified sales trainer 🙂

2:03 – Dom tells us how he went from being a writer to getting recruited by ZocDoc, to helping companies build scalable sales efforts.

8:00 – Storytelling as a tactic for Aligning Value!  This is it, people! We always talk about it and it’s finally here. This how you get buy-in from multiple stakeholders with multiple problems.

10:00 – Inside sales vs. Enterprise sales: With inside sales, you get about 12x as many chances to practice selling a month. This constant feedback is what you need to become an expert salesperson. Dom shares a story you HAVE to hear.

13:52 Dom’s got both inside and enterprise sales experience at ZocDoc. The only people who survived got really good at pattern recognition.

18:12 – The same mistakes keep being made by enterprise sales people: Too much reliance on their deck.

19:51 – Enterprise sales is changing. A lot of times it’s not that they don’t think your solution is good enough it’s that they can’t agree internally on what the problem is. “You need to know the players but if you pitch what they each get out of it, often what they get out of it is in conflict with each other. What you need to do is help them build consensus that each of their pain points are a result of a problem that you can help them solve. “

21:43 – The end-user is usually your foot in the door. You need to give them the tools to sell to everyone else. Facilitate consensus on the problem then consensus on the solution. A good pitch and getting people excited is just the beginning. Navigating enterprise sales is a project management function.

25:46 – Are you experiencing the pain points we can solve for you? What are those pain points costing you? Here is why these pain points are happening to you. If you sell different problems causing the pain point to different people in sales cycle there’s no shared common insight that allows people to buy in an enterprise sale.

30:23 – Whoever you’re selling to has 500 problems they have to solve every day. The one problem that I solve, I see 500 times a year and I can offer help in that problem because I know why that problem is happening to them. Just be valuable.

34:22 – Tools and tactics for inside sales. When trying to get attention, the key is relevance. What is the most relevant piece of information that you have on that person?

37:22 – Tools and tactic for enterprise sales. The principles are the same. Don’t just reach out to one person. Whoever it’s relevant for will respond. The relevance hooks are always different but I always reach out to at least 5 people. Follow up is huge. The second email has double the response rate of initial email.


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About Dom Cappuccilli

Dom Cappuccilli has helped hundreds of entrepreneurs to not only tell a better sales story, but also built many of their sales efforts from the ground up. He combines the power of a trained storyteller with the real world experience of an elite salesperson. In fact, he became an elite salesperson because he was a trained storyteller.

After 10 years as a reporter, author and screenwriter, Dom found his calling when he rewrote the sales story of a fast-growing healthcare company and doubled their revenue in six months. From there, he quickly rose to be a sales leader at unicorn startup ZocDoc – currently valued at $1.8B – before going to Arches Technology where he created and sold an entirely new healthcare technology product to health systems.

During his time in the startup and small business world, Dom met many founders and was amazed that almost all of them were succeeding in spite of their sales effort and strategy, not because of it. The Clean Sell was born soon thereafter and in time since its founding has helped hundreds of entrepreneurs to not only tell a better sales story, but also built many of their sales efforts, processes and teams from the ground up.

LinkedIn Dom Cappuccilli


About The Clean Sell

We help founders & CEOs turn their subject matter expertise into a structured, scalable and simple sales process that fuels their growth.

The Clean Sell is a B2B sales consultancy helping everyone from startups to Fortune 500 companies to create a structured, scalable and simple sales effort in line with best practices. Throughout a company’s lifecycle, there are key inflection points where a lack of sales knowledge and process can sabotage a business that should be thriving. We fill these gaps for our clients.

No matter what stage you’re in, we have the right solution for you.

Facebook TheCleanSell

Twitter TheCleanSell


Related and/or Mentioned on the Show

Whitepaper: The 7-Step Pitch Structure

The Clean Sell Blog


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