New episode on the Vibescaling Podcast, Sam Berg! Was cool to get another health tech startup (with Raph Parker being our first), it’s a space I’m less familiar with but Tennr is ripping.
Been awesome doing these and have so many in the hopper (see below).
Some of our previous guests:
Todd Busler, CEO @ Champify - see writeup here
Raphael Parker, CRO @ Mandolin (former founding GTM hire @ Segment) - see writeup here
Kyle Parrish, former VP of Sales @ Figma, see article here
Liam Mulcahy, GTM operating partner @ Kleiner Perkins, see article here
Pat Forquer, CRO @ Legora, see article here
Mike Donohue, CRO @ Maven, see article here
Tomer Chernia, VP of GTM @ Cursor, see article here
Some of our future guests for Season One:
Jack Gashi, VP of Sales @ Avoca (recorded, in edits now)
Eleanor Dorfman, Head of Sales @ Anthropic (recorded, in edits now)
Ghazi Masood, CRO @ Replit (recorded, in edits now)
Jason Miller, VP of Sales @ Unify (recorded, in edits now)
Kyle Norton, CRO @ Owner.com
Jason Gelman, Operating Partner @ Primary Ventures
Evan Cassidy, VP of Sales @ Decagon
Liam Mulcahy is coming on again!
Mike Heller, Partner @ Floodgate (former Dropbox & Clearbit GTM)
Rob Saliterman, VP of Sales @ Harvey
Jaquelyn Goldberg, VP of Sales @ Unframe
& others from our portfolio companies @ vibescaling
And many more in the pipeline - if you know any good leaders who fit this, shoot me a DM on LI or reply to this email. We’ll keep openings rolling and be super open to suggestions for similar guests.
We film in-person in SF & NYC at legit podcast studios and have hired a new post-production agency, so the quality will be high - see below for a snippet in-studio behind the scenes.
Interviewing the awesome Ghazi Masood, CRO @ Replit, in our NYC studio in February
Links To Sections
VibeScaling Episode 8: Sam Berg
Really enjoyed this one with Sam.
Was great getting my food choices in NYC roasted from a fellow Long Islander (albeit, he’s from Brooklyn 😆). Shoutout to Katz’s & Carbone and to my unsophisticated pallet.
Loved how direct and honest Sam was, and it was interesting learning more about how healthcare companies are using tools like Tennr to grow their business (health tech is definitely a space that isn’t in my sweet spot, along with B2C).
Hope you all enjoy!
Sam’s Background
Sam Berg is the VP of Sales at Tennr, one of the fastest-growing companies in the healthcare AI space.
Sam leads Tennr’s sales org during a period of hyper-growth, where he’s laser-focused on building disciplined sales teams while scaling a high-trust sales motion.
Before Tennr, Sam spent nearly 8 years at VTS (formerly Hightower), where he rose from individual contributor to sales leader, helping to scale an enterprise sales org selling into commercial real estate brokers.
Like many other great sales leaders, his career had a seemingly innocuous start: selling tickets to New York Islanders games and building a customer-first sales approach in the process.
Interesting Takeaways
Never Split the Difference is a discovery book, not a negotiation book. Sam expected Chris Voss to teach him how to close. Instead, the biggest unlock was tone, language, and how to extract information without making prospects feel interrogated. It's also a team selling book - eight ears on a call is better than two.
The words you use reveal whether you're a seller or a partner. "Deal" sounds transactional - say "partnership." "Cheap" implies poor quality - say "inexpensive." "Feedback" has a negative connotation - say "advice." Sam flips "cheap" back on competitors intentionally: "Their solution is definitely cheaper than ours."
"Eight Mile yourself" in competitive situations. Proactively address your weaknesses before the competitor does. "I know what they're going to say about us. And if that's the thing that's really important to you, you should go with them. But if this is what matters, here's why we're different."
Coachability is 40% actively seeking coaching, 60% implementing it fast. Being "open to feedback" is table stakes. Sam doesn't care about that. What separates candidates is whether they ask for advice unprompted and then reference it in a follow-up email showing they actually absorbed it.
The only goal on a cold call is to sound confident and not risky. Same script, different delivery. Leaning forward with upward inflection versus laying back with a steady cadence completely changes how you're perceived. Posture and tone matter more than the words.
Test for discipline with one question: "What did you do to prepare for this interview?" If they squirm, they'll squirm on prospect calls. Sam follows up with: "If we were in your book of accounts, why would or wouldn't we be ICP?" That tests critical thinking on top of prep.
Discussed In This Episode
From $8/hour ticket sales to VP of Sales - how early habits compound
Why discipline and curiosity matter more than talent (and how he actually tests for them in interviews)
His sales interview philosophy: preparation over polish
The competency framework he built to promote SDRs into enterprise reps
Why great sellers sound calm by using trust signals
Transparency breaks patterns - how setting negotiation guardrails builds trust
Why he avoids words like "deal" and "feedback" and how language subtly shapes buyer behavior
How to find the real urgency that accelerates enterprise deals
Why creating context beats jumping to discovery
Why competition fuels the best sales teams pushing to out-execute each other
Timestamps
(00:00) Intro, Brooklyn vs. Long Island debate & why food opinions matter more than sales titles
(05:00) From club promoting to ticket sales: getting paid $8/hour and taking “small” sales seriously
(10:00) Early account research hacks & learning willingness-to-pay the hard way
(16:00) “I don’t want to sell glass seats. I want to buy them”: deciding to leave sports for software
(21:00) Breaking into software sales, early career mistakes & choosing the small pond over the big logo
(27:00) Selling outcomes vs. features: the inflection point that changed how he sold forever
(33:00) Transparency as a sales weapon: naming weaknesses, breaking patterns & earning trust
(39:00) Internal vs. external change: what actually creates urgency in enterprise sales
(45:00) From Hightower to Tennr: why vertical, “unsexy” industries are the best place to sell
(50:00) Joining Tennr early: hypergrowth energy, imposter syndrome & “Hamilton-level” intensity
(55:00) Building a sales team from scratch: why discipline and curiosity beat raw talent
(01:01:00) How he interviews sellers: testing preparation, hypotheses & real curiosity
(01:07:00) Tone, cadence, and posture: why great sellers sound calm instead of clever
(01:12:00) Words that kill trust (“deal,” “feedback”) and what to say instead
(01:17:00) Healthy sales competition: winning on execution, not hoping teammates fail
Thanks for tuning in!
If you enjoy it, please give us a rating, review, or follow on Spotify/YouTube/Apple Podcasts - it really helps us grow this.
For those who are new, my name is Chris Balestras, partner @ Vibescaling - a GTM advisory, recruiting, media, and investing firm, working with seed through series C AI-natives to help them grow.
Where to find Vibescaling:
We work with many of the hottest AI-native startups in various capacities, and for those who are interested, shoot me an email at [email protected] or a DM on LI.
🫡 cheers,
Chris