Vibescaling Podcast
Vibescaling
The 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 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.
Find us @ https://www.vibescaling.ai/ & https://www.vibescaling.blog/
Every week, host Chris Balestras, partner @ Vibescaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with 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.
Find us @ https://www.vibescaling.ai/ & https://www.vibescaling.blog/
Episodes
Mentioned books
9 snips
Mar 24, 2026 • 1h 8min
How The Best CROs Actually Hire Salespeople w/ Kyle Norton, CRO @ Owner.com
Kyle Norton, CRO of Owner.com and former Shopify/League sales leader, shares hiring and scaling lessons. He debunks charisma-driven hiring, explains why organized operators win, and reveals how early RevOps, enablement, and centralized AI accelerate growth. He also covers rigorous diligence when joining companies and building repeatable sales systems.
18 snips
Mar 17, 2026 • 49min
My #1 Rep Closed $3.5M & Never Sold A Day In Their Life w/ Ghazi Masood, CRO @ Replit
Ghazi Masood, CRO at Replit and former GTM leader at Retool and Auth0, shares hiring and GTM playbooks for AI-native developer tools. He explains why nontraditional sellers can close huge deals, the panel presentation interview test, renaming SEs to Field Engineers, and using Replit to dogfood CPQ and SDR workflows. He also breaks down demand-driven hiring and building distribution as a moat.
27 snips
Mar 10, 2026 • 57min
Why Anthropic is The Hottest Company in AI & & How To Use Claude As A Seller w/ Eleanor Dorfman, Head of Industries @ Anthropic
Eleanor Dorfman, Head of Industries at Anthropic and veteran GTM leader, explains her jungle-gym career path and the persistence that got her into startups. She discusses what makes sellers AI-native, how Claude is used for prototyping and deal work, why “not technical enough” is a lazy critique, and how enterprise-first AI selling looks in practice.
11 snips
Mar 3, 2026 • 23min
11 Traits That Make A Hot Sales Job & How To Avoid Joining A Dud
Clear checklist for picking a career-making sales role. Why joining talent mafias and getting strong inbound tailwind matters. The sweet spot of Series A–C and the importance of a path to $100K+ deals. How selling technical, complex products and validating engineering velocity protects your pipeline. Why AI-native sales leadership and in-person presence speed career momentum.
14 snips
Feb 24, 2026 • 55min
The Art & Science Of Choosing Which Startup To Join & How To Value Your Equity w/ Billy Gallagher, CEO @ Prospect
Billy Gallagher, founder and CEO of Prospect and former Khosla Ventures investor and early Rippling employee, helps startup employees manage private equity. He breaks down quantitative signals like investor quality, headcount, and secondaries. He also covers founder experience, the Series A–C breakout window, tools to research startups, and practical equity mechanics such as options vs RSUs and negotiation priorities.
11 snips
Feb 17, 2026 • 1h 5min
The Best Sales Reps Are Coin Operated & All Roads Lead Back To The Steak Dinner w/ Jack Gashi, VP of Sales @ Avoca
Jack Gashi, VP of Sales at Avoca and veteran sales leader from Yext to Check, shares candid stories from boiler‑room cold calls to building GTM teams. He discusses trust‑first vs fear‑first sales cultures. Conversations hit career disillusionment, why top reps are coin‑operated, the spreadsheet cost of losing talent, and why face‑to‑face steak dinners still close deals.
12 snips
Feb 10, 2026 • 1h 6min
The Words You Use Are Killing Your Trust & What Great Sellers Do Instead W/ Sam Berg, VP of Sales @ Tennr”
Sam Berg, VP of Sales at Tennr who scaled disciplined, trust-first sales teams during hyper-growth, shares sharp takes on sales language, hiring frameworks, and building negotiation guardrails. He breaks down why discipline and curiosity beat polish, how to create urgency without pressure, and which words kill trust — plus simple swaps that keep conversations calm and credible.
14 snips
Feb 3, 2026 • 58min
Why You Should Join Cursor Over OpenAI and Anthropic & How To Avoid Bad Sales Hires W/ Tomer Chernia, VP of GTM @ Cursor
Tomer Chernia, VP of GTM at Cursor and seasoned go-to-market leader, talks hiring mastery and rapid GTM scaling. He explains interactive interview techniques, the “three hows” test, why Cursor competes with big AI firms for talent, and how outbound is becoming signal-driven. Short, practical, and full of sharp hiring and sales process rules.
21 snips
Jan 28, 2026 • 1h 1min
Jack Dorsey Hired Me from My Dorm Room As Employee 100 @ Square | Mike Donahue, CRO @ Maven AGI
Mike Donohue, CRO at Maven AGI and early Square hire, scaled sales teams at Leanplum, PayPal, and Gupshup. He recounts getting hired by Jack Dorsey from his dorm, the athlete mindset in sales, and why sales is a repeatable science. He explains where AI agents drive ROI in customer support, how to hire AI-native GTM teams, and practical tools and playbooks for scaling revenue quickly.
13 snips
Jan 22, 2026 • 1h 2min
How I Built Legora's GTM Motion To A $1B+ Valuation w/ Patrick Forquer, SVP Global Revenue @ Legora
Patrick Forquer, SVP of Global Revenue at Legora, shares insights from his impressive journey in sales, scaling companies like Braze and leading Legora to a billion-dollar valuation. He highlights why selling AI differs from traditional SaaS, emphasizing the importance of deployment and change management in vertical markets. Patrick discusses the accelerated deal velocity and the need for responsiveness in sales. He also reflects on hiring traits for energetic, organized team players and shares how pilots are vital for demonstrating value in immature markets.
