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
May 12, 2026 • 44min
How We Built Profound’s GTM Motion To A $1B+ Valuation w/ Mark Ebert, SVP of Revenue @ Profound
Mark Ebert, SVP of Revenue at Profound and former leader at 6sense and Oracle, shares sharp GTM moves and hiring instincts. He breaks down sales-led enablement, the three-path whiteboard for planning deals, WWII-inspired POC strategy, why he hires reps from scrappy #3 players, and how LLMs are collapsing the B2B funnel and becoming the new ultra customer.
4 snips
May 5, 2026 • 47min
Why "AI for Finance" Is Meaningless & Why Bankers Make the Best Sellers W/ James White @ Rogo
James White, VP of Sales at Rogo and veteran seller of market-data and financial software, shares his journey from CompUSA to building sales teams for finance AI. He discusses why “AI for finance” is too broad, how bankers make elite sellers, Rogo’s GTM Associate program, and why focusing on investment banking and product-led hiring unlocked rapid enterprise adoption.
11 snips
Apr 28, 2026 • 56min
The Old Sales Playbook Is Dead: Hiring + Selling In The AI Era w/ Jacquelyn Goldberg, VP Sales @ Unframe AI
Jacquelyn Goldberg, VP of Sales at Unframe AI and seasoned early-stage GTM lead, talks hiring and selling in the AI era. She covers which industries adopt AI fastest. She explains how to assess candidates, teach discovery, and spot grit. She outlines AI literacy tiers and why pipeline problems are often thinking problems. She also describes what’s actually working in outbound and why the rolodex is the lowest hiring bar.
7 snips
Apr 21, 2026 • 58min
Tell Them the Movie Before They Watch It: Enterprise Sales, Champion Building & the No-Pilot Stance W/ Adam Ali, SVP Revenue @ Rox
Adam Ali, SVP of Worldwide Revenue at Rox and former sales leader at Glean and Rubrik, shares his playbook for scaling enterprise sales. He talks about champion building vs coaching, shadow selling between meetings, the no-pilot stance and EB go/no-go, and his “tell them the movie before they watch it” approach to proofs of value.
Apr 14, 2026 • 52min
Fewer Reps, More Pipeline: How AI-Native GTM Teams Are Doing More With Less w/ Jason Miller, VP Sales @ Unify
Jason Miller, VP of Sales at Unify and former Monday.com sales leader who scaled teams through hypergrowth and IPO. He dives into signal-based selling and bespoke buyer signals. He explains why some data sources are off-limits and how to combine signals, enrichment, and sequencing. He also covers hiring philosophy, building high-leverage reps, and the ideal AI-native GTM toolset.
5 snips
Apr 7, 2026 • 59min
How to Reinvent Yourself & The Athlete Mindset Behind Elite Sales Teams w/ Evan Cassidy @ Decagon
Evan Cassidy, VP of Sales at Decagon who scaled GTM from first sales hire to Series A–D and was a competitive rower. He tells stories of reinvention, breaking into tech after rejection, and building high-speed, team-first sales cultures. He also discusses hiring traits that matter beyond athletics and why joining the AI wave now can compound career advantage.
13 snips
Mar 31, 2026 • 1h 4min
The $1M Salary GTM Role Nobody Qualifies For Yet w/ Jason Gelman, GTM Partner @ Primary VC
Jason Gelman, Go-to-Market Operating Partner at Primary VC who built Market Dev and GTM engineering programs. He discusses Primary’s hands-on portfolio support, a centralized Market Dev outreach advantage, the new go-to-architect role, why AI-native + legacy SaaS fluency will command massive pay, and how full-stack GTM people and P&L-first sales tech will reshape small, highly productive teams.
22 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.
31 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.
40 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.
