Winning Strategies from Gridiron Grit to Healthcare Innovation | Jay Kleinman, Ep 05
Episode Summary
Jay Kleinman, a 30-year healthcare sales and business development veteran, discusses how lessons from playing D1 football at Auburn under Pat Dye shaped his approach to building commercial teams for early-stage healthcare companies. He covers segmentation strategy, discovery-based selling, and the transformation of elder care through digital health and telemedicine adoption accelerated by COVID-19.
Pull Quotes
“I expect and know that I can win, but I can't do it by myself. How do I embrace my clients or support teams, whatever, to help me win? Because when I win, they win.”
“I really like to spend more time with my clients talking about the deals that they've won, not the deals that they've lost. Let's talk about the deals you won, why you won them, what was done right, and then how do you exploit that moving forward.”
“Volume is not necessarily what wins in sales anymore. The most calls or the most knocks on the door or the most emails. Your prospects are getting hundreds of touches a day. You got to figure out a way how you're going to differentiate yourself, how are you going to do something that makes your prospect feel special or that you know something about them.”
On founder's disease in early-stage sales
“Everybody already knows the value of your product. All you do is talk about your features and your features and your features. You're not delivering any benefit or value to your prospect, and to that prospect specifically.”
On selling SaaS to IT buyers who serve internal end users
“Sometimes your customer is not your customer, and those are complicated sales, right? And you have to understand that or else you're not going to make the sale.”
Transcript
Hi, welcome to Tales from the Skyland, a podcast about business consulting and venture investing where we talk to people who are getting out there in the world and making this stuff happen today. In the Sky Lounge we have Jay Kleinman. Hi Jay, welcome to the Sky Lounge.
Hey, doing well, great.
Why don't you tell us a little bit about yourself?
Sure, happy to be here, thanks for including me. Jay Kleinman, I'm a longtime business development and sales strategy guy, primarily in the healthcare space. Been doing this about 30 years. Worked for some large organizations like Tenet Healthcare or WPP companies in the communication space. Helped Tenet launch a revenue cycle business about eight years ago, ConforHealth Solutions, that was probably my biggest, most successful funding startup that I ever did. Over the last 10 years, I've really been spending most of my time in early stage companies, venture-backed companies in the healthcare space and analytics and SaaS and in the services side. So I've been there a while, mainly again focused on commercializing businesses, go-to-market strategies in direct sales.
Awesome. Early in your career, did you have any mentors that particularly helped you along the way?
Want to go deeper?
Work With MeRelated Episodes
Founders: These Are the Mistakes You Don't Know You're Going to Make | Steve Walsh, Ep 52
Steve Walsh, an angel investor and startup advisor, shares lessons from 25 years building multi-billion dollar B2B divisions at Cox and Comcast before transitioning to helping early-stage founders. He discusses common founder mistakes, when to raise capital, the importance of customer validation before building product, and how he filters 6,000 conversations down to 69 investments through rigorous vetting and founder education.
Leadership, Resilience, and Sales Mastery | Rich Makover, Ep 16
Rich Makover, a fractional Chief Revenue Officer and executive coach at TechCXO, discusses his journey from Penn State lacrosse player to CPA to sales leadership at Avon and beyond. He shares insights on hiring athletes for sales roles, the importance of resilience over winning, situational coaching methodologies, and his transition to fractional leadership and executive coaching, including his decade-long mentoring program for Penn State lacrosse.
The CEO Is the Salesperson: Why Founders Can't Hand Off the Pitch | Jen Bonnett, Ep 49
Jennifer Bonnett, a longtime tech entrepreneur and former ecosystem builder at ATDC and Invest Atlanta, discusses her transition back into technology through AI experimentation. She shares lessons from building a search engine in 1997, her current work vibe coding consumer apps with Claude, and her philosophy that CEOs must personally sell for at least the first year before delegating. The conversation explores how AI is lowering barriers to entrepreneurship while emphasizing that founders still need strong networks, customer discovery skills, and the discipline to market early.