The Words You Use Are Killing Your Trust & What Great Sellers Do Instead W/ Sam Berg, VP of Sales @ Tennr”
Vibescaling Podcast
Breaking into startup software
Sam recounts early software roles, a short startup stint, and choosing a small‑pond opportunity at Hightower.
Sam’s BackgroundSam 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.
Sam builds sales teams and systems that scale by earning trust, not burning it.
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 > 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
About The Vibescaling PodcastThe Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.
Every week, host Chris Balestras, partner @ Vibescaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.
No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.
About Vibescaling
Vibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.
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