BC Startup Sales Podcast – Selling Wellness Software with Dan Kessler (Headspace)

This week, the Bowery Capital team hosted Dan Kessler, VP of Business Development at Headspace, to discuss “Selling Wellness Software.” Headspace is digital service and app that offers hundreds of guided meditations designed to help with everything from stress and anxiety to relationships and sleep. Selling wellness software is a topic that we have not really covered on the podcast. We were excited to talk with Dan around how to think about selling wellness software and other types of products that generally fit the “soft ROI” bill. He was a great guest with a ton of knowledge on the topic having been with the company for a number of years.

Dan Kessler is the VP of Business Development and Partnership at Headspace, a company dedicated to improving health and happiness in the world through meditation. Before joining Headspace, Kessler served as the SVP of Operations and Strategy at Hallmark, co-founded Palindrome Media, and worked in business development for Happy Madison (at Sony Pictures Entertainment). Kessler earned a degree in Physics and English Comparative Literature from Columbia University before receiving an MBA from Stanford University.

Dan and I start the discussion around his background and Headspace in general. In particular, we speak a lot about Headspace and their consumer business which remains large and growing with tens of millions of users. We then talk through how they translate that into business to business success through free and freemium accounts. Selling wellness software is not something that is easy and so Dan and I speak a bit about their compelling narrative and how they framed up the initial pitch for the business. There are a lot of interesting things that we all consider “weird” that they use to frame how Headspace matters and is relevant to any company. Essentially they completely reframed the narrative early on. We also dig in around the difficult selling modality of soft ROI versus hard ROI. Dan gives some interesting points of view on replacement of other products and how you can use brand positioning to win. Dan and I then walk through some of the positive and negative trends that exist in the workplace that has helped their selling model. We talk about some of the unique things around process and systems that Headspace is working on as well as their view of lead qualification.

If you liked “Selling Wellness Software” and want to read more content from the Bowery Capital Team, check out other relevant posts from the Bowery Capital Blog. If you haven’t already, subscribe to the podcast to get all our new content each week!