Technology

The Crew Podcast

The Crew Podcast interviews GTM leaders and investors at top AI startups and early-stage companies.

Every week, host Chris Balestras, co-founder @ Crew (a GTM recruiting, media, & investing firm for seed through series D 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.withcrew.ai/ & https://www.withcrew.blog/

Latest Episodes:

The $1M Salary GTM Role Nobody Qualifies For Yet w/ Jason Gelman, GTM Partner @ Primary VC Mar 31, 2026

Show notes

Jason Gelman’s Background

Jason Gelman is a Go-to-Market Operating Partner at Primary Venture Partners, one of the largest early-stage VC firm that just closed its $625 million Fund V (the largest to date) a few days ago, bringing total AUM to ~$1.6B.

Before Primary, Jason led Revenue Strategy & Operations at Compass, helping scale the company from ~$100M ARR to $6B through their IPO. He got his start in the New York tech scene after attending law school, where he quickly realized the meritocracy of tech was a better fit for him than the rigid hierarchies of the legal world. He’s never looked back.

At Primary, Jason has built out two core programs for portfolio companies: a Market Development team (centralized BD outreach on behalf of founders) and a Go-to-Market Engineering program (tech stack buildout and systems architecture). He's also leading the development of the firm's investment thesis around go-to-market tech.

Discussed In This Episode

• How Primary's portfolio support model actually works and why "advice-giving" doesn’t cut it

• The Market Dev team's unfair advantage: why outreach from Primary converts better than any vendor pitch

• The Go-to-Market Architect role: why it's different from a GTM Engineer (and why Clay's definition falls short)

• Why a profile with deep experience in legacy SaaS tools + fluency in modern AI will easily earn $500K to $1M+/year

•How to find the rare 3-in-30: RevOps chops + AI fluency + business acumen

• The Full Stack GTM person: one role replacing marketer + SDR + AE

• How the PNL test should filter every sales tech investment and why the old "time savings" ROI story is dead

• Where Salesforce is headed in the next 10 years and why its pricing leverage is finally at risk

• Why Slack might be Salesforce's best asset going forward

• Small teams doing massive revenue: what $1M+ IRR per employee actually looks like

• How to break into VC from a go-to-market background

Timestamps

(00:00) Intro & Jason's Background: From Law School to NYC Tech

(07:15) The Go-to-Market Operating Partner Role: What It Is (and Isn't)

(11:38) How Primary's Portfolio Support Programs Were Built

(16:42) The Market Development Team: Primary's Unfair BD Advantage

(21:26) Go-to-Market Engineering: Building the Stack for Founders

(25:43) The GTM Architect vs. GTM Engineer and Why the Distinction Matters

(30:09) Why This Profile Will Earn $500K–$1M+ and How to Find One

(34:21) The Full Stack GTM Role: One Person Replacing Three

(37:07) Primary's Investment Thesis: The PNL Test for Sales Tech

(42:30) Where Salesforce Is Headed and Why Its Grip Is Finally Slipping

(49:04) Small Teams, Massive Revenue: GTM Efficiency Benchmarks

(55:35) How to Break Into VC from a Sales/GTM Background

About The Vibescaling Podcast

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 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.

Where to Find Vibescaling

LinkedIn: https://www.linkedin.com/company/vibescaling/

YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg

Newsletter: https://www.vibescaling.blog/

Website: https://www.vibescaling.ai/

How The Best CROs Actually Hire Salespeople w/ Kyle Norton, CRO @ Owner.com Mar 24, 2026

Show notes

Kyle Norton is the CRO of Owner.com, the all-in-one online presence platform for independent restaurants: think Shopify Plus meets HubSpot, but built specifically for your neighborhood restaurant that’s your go-to for ordering in on a Thursday night. He's taken Owner from $2.5M ARR to $100M in just under four years, with 2025 growth outpacing 2024.

Before Owner, Kyle spent three years at Shopify where he built out the Point of Sale go-to-market organization and then ran the Canadian market, which is a quarter-billion-dollar business. Prior to Shopify, he was the first-time VP of Sales at League, taking them from 0 to $25M ARR. Kyle started his career in sales in 2008 during the financial crisis (tough timing that forged a great seller) and has been building and rebuilding revenue teams ever since. He was only an individual contributor for 14 months total before moving into leadership, which speaks volumes.

Kyle recently relocated from Toronto to San Francisco, and he'll be the first to tell you the dinner conversations there are on another level. He works basically nonstop, thinks deeply about first principles, and has a well-known polarizing style: intense, hyper-transparent, and deeply opinionated about language and systems.

Discussed In This Episode

• Why case study scores have almost no correlation with rep performance

• The halo effect in hiring: how charisma hijacks your scorecard and what to do instead

• Why "organized operators" consistently outperform charismatic closers at Owner

• The barbell happening in both companies and talent and what it means for your career right now

• Why a VP of Sales title at a mediocre company is a worse bet than first-line manager at a world-class one

• How to do real diligence on a company before joining: who to talk to, what to ask, how to find the dirt

• Why Kyle brings in Rev Ops and Enablement earlier than almost anyone and the exact 80/20 moves to start with

• Centralized vs. decentralized AI strategy and why Owner chose to keep it centralized

• The AI tools giving Owner a real edge: Avira for rep training, Triggers for post-sales, OneMind for AI-native selling

• How Kyle uses Claude Code as a personal chief of staff, from performance reviews, to weekly updates, and more

Timestamps

(00:00) Intro & Kyle's Move from Toronto to SF

(04:00) Starting a Career in Sales During the 2008 Financial Crisis

(10:00) League, Shopify, and the Path to Owner.com

(16:00) What Owner.com Actually Does (and Why Their Model Works)

(22:00) Joining Owner: Talent Assessment, Radical Transparency, and Mutual References

(30:00) Why Case Studies Are Broken (Sort Of)

(38:00) The Halo Effect, Scorecard Hiring, and Why Operators Win

(44:00) The Barbell: Companies, Talent, and Career Selection in 2025

(52:00) How to Actually Diligence a Company Before You Join

(58:00) Hire Rev Ops & Enablement Earlier Than You Think

(01:04:00) Centralized AI Strategy: How Owner Builds, Deploys, and Adopts AI Tools

(01:12:00) Kyle's Personal AI Stack: Claude Code, Open Claude, and Building Your Own Chief of Staff

About The Vibescaling Podcast

The Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.

No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.

About VibescalingVibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.

Where to Find Vibescaling

LinkedIn: https://www.linkedin.com/company/vibescaling/

YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg

Newsletter: https://www.vibescaling.blog/

Website: https://www.vibescaling.ai/

My #1 Rep Closed $3.5M & Never Sold A Day In Their Life w/ Ghazi Masood, CRO @ Replit Mar 17, 2026

Show notes

Ghazi’s Background

Ghazi Masood is the CRO at Replit, one of the most talked-about companies in the AI era, building what they consider to be the only credible end-to-end vibe coding solution for enterprises.

Before Replit, Ghazi was VP of Sales at Retool, where he helped scale one of the most elite GTM teams in developer tooling.

Before that, he spent 4+ years at Auth0, joining early and leading all aspects of revenue growth for the Americas - scaling from $28M to $300M+ in 4 years before Okta acquired Auth0 for $6.5B in 2021.

Ghazi is one of the most respected GTM leaders in the developer tooling and technical products space - it was fun to dive into his philosophy on hiring nontraditional sellers, why most companies staff for aspiration instead of demand, and how the AI era is fundamentally changing the way enterprise sales orgs are built.

Discussed In This Episode

• Why Replit's #1 seller closed $3.5M and had never sold a day in his life and what that actually means for how AI companies should hire

• The "panel presentation" interview format and why Ghazi makes every candidate show what they've built in Replit before they get the job

• Staff demand, not aspiration and the back of the napkin math every sales leader needs to do before hiring their first rep

• Why Ghazi renamed his SEs to "Field Engineers" and rewrote the traditional pre/post-sales model

• The work hard, play hard culture that made Auth0 special and how he's rebuilding it at Replit

• Back channeling done right and why he never calls the references candidates give him

• Why tenure is the most underrated signal in a sales resume right now

• The founders' mistake he sees over and over: hiring a VP of Sales too early

• How Replit is using its own product internally from CPQ tools to SDR call scripts

• Why distribution is the new moat (not technology) and what that means for how you build a GTM org in 2025

Timestamps

(00:00) Intro, What Replit Is Building & Why Ghazi Joined

(04:00) Building the Auth0 Culture: Work Hard, Play Hard & The Off-Sites That Actually Mattered

(12:00) From Auth0 to Retool: What Great GTM Culture Actually Looks Like

(18:00) Why Replit's Best Reps Have Never Sold Anything and How Ghazi Finds Them

(26:00) The Panel Presentation: Ghazi's Highest-Signal Interview Step

(32:00) How AI Is Changing the Sales Org Structure and Why Field Engineers are Replacing SEs

(38:00) Staff Demand, Not Aspiration: The Back of The Napkin Math Every Founder Needs to Do

(44:00) What to Ask in a VP of Sales Interview to Know If the Pipeline Is Real

(50:00) Back Channeling, Tenure & How Ghazi Actually Evaluates Candidates

(56:00) Hiring Senior Sales Leaders Too Early, Distribution Is the Moat & The Advice He Keeps Giving Founders Who Won't Listen

About The Vibescaling Podcast

The Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.

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.

Where to Find Vibescaling

LinkedIn: https://www.linkedin.com/company/vibescaling/

YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg

Newsletter: https://www.vibescaling.blog/

Website: https://www.vibescaling.ai/

Why Anthropic is The Hottest Company in AI & & How To Use Claude As A Seller w/ Eleanor Dorfman, Head of Industries @ Anthropic Mar 10, 2026

Show notes

Eleanor Dorfman is the Head of Industries at Anthropic, where she leads enterprise go-to-market for Claude at the epicenter of the AI revolution.

Before Anthropic, Eleanor built and scaled GTM teams at some of the most talent-dense companies of the last decade. She started her career at Clever (where she turned multiple rejections into an eventual yes through sheer conviction and follow-through), moved to Segment, where she transitioned from customer success into sales and built the expansion motion, and then joined Retool as an early sales leader, helping scale the org through hypergrowth.

She also advises early-stage companies and has worked closely with venture firms like Thrive Capital giving her a front-row seat to how breakout startups are built and how early GTM hires play a mission-critical role in either accelerating or stalling that trajectory.

From public education to developer tooling to AI labs, Eleanor’s career looks less like the traditional “ladder” and more like what she aptly describes as a “jungle gym.”

Discussed In This Episode

• Why careers are a jungle gym, not a ladder and how to pivot on “one foot”• Getting rejected (and rejected again) and why persistence + conviction still win• The moment she realized sales was about energy, not personality

• What makes a seller truly AI-native and how top reps are using Claude today

• How to use Claude Code to build live prototypes (and why you may no longer need your sales engineer)

• Why “not technical enough” is often a lazy hiring critique

• The curiosity test: the one interview question that flipped her from “no” to “yes”

• Why early startup hires require a founder mentality

• The “ego death” principle and how ego hinders hypergrowth

• Why she doesn’t care about “productive capacity” in the AI era

• Learning vs. earning vs. values and the difference between Anthropic vs. other AI-natives

• Why Anthropic is enterprise-first and what that means for sellers

Timestamps

(00:00) From paralegal to public education to startup life

(05:10) Rejected three times by Clever and why she kept coming back

(11:30) Transitioning from customer success into sales at Segment

(16:45) Building the expansion sales motion and falling in love with sales

(24:46) Retool, hypergrowth, and scaling GTM in developer tooling

(29:30) How to break into an AI lab (and what actually gets a recruiter’s attention)

(32:09) Ego death, ownership, and what real commitment looks like

(39:00) The myth of “not technical enough” in early GTM hiring

(42:43) Claude’s personality: designed, not accidental

(44:30) How top reps use Claude Code to build live demos mid-cycle

(45:11) Managing in the AI era: throw out productive capacity, optimize for learning

(52:24) Why Join Anthropic

(58:26) Learning, earning, values and how to play for “the front of the jersey”

About The Vibescaling PodcastThe Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.

No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.

About VibescalingVibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.

Where to Find Vibescaling

LinkedIn: https://www.linkedin.com/company/vibescaling/

YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg

Newsletter: https://www.vibescaling.blog/

Website: https://www.vibescaling.ai/

11 Traits That Make A Hot Sales Job & How To Avoid Joining A Dud Mar 03, 2026

Show notes

This week, Chris goes solo. No guest necessary as he breaks down the answer to the question he’s gotten asked more times than he can count: how do I actually choose the right sales job?

Chris has spent several years navigating this himself, written articles on it, and interviewed enough VPs of Sales and CROs to know what separates career-defining moves from ones that stall your career trajectory without you even realizing it. The result? His 11 traits framework, which is a crystal clearest distillation of what makes a sales role genuinely great.

Discussed In This Episode

• The #1 thing the happiest, most successful people in Chris's network all have in common, and why most people make the mistake of not prioritizing it

• GTM mafias and talent vortexes: why 90% of the time, the people landing the best jobs have a champion on the inside

• Why OpenAI and Anthropic are career insurance, and what that snowball effect actually looks like in action

• The "breakout period" of the Series A through C sweet spot that startup veterans optimize for, and why the AI natives have blown up the old ARR benchmarks

• The inbound tailwind test: if more than 30% of deals are outbound, what that signals about the environment you're walking into

• Why some of Chris's friends joined PLG companies with tons of inbound but still hated the job

• The path-to-enterprise question every seller needs to ask before signing an offer, and why $100K deal size is the minimum bar he'd set

• Selling complex products vs. app layer and why Chris wishes he'd gone more technical earlier

• What "AI native" sales leadership actually looks like vs. the dinosaur playbook

• Why in-person matters in the AI era, and the Keith Rabois framing that explains the feedback loop advantage

• How to do due diligence on engineering shipping velocity before you join, and why it directly affects your close rate as an AE

• Back channeling the right way: who to actually talk to, why VCs don't know what you need to know, and why Repview has its limits

Timestamps

(00:00) Why Chris Is Going Solo For This Episode

(02:22) Trait #1: Join a Mafia or a Talent Vortex

(04:45) Trait #2: Clear Signs of Market Pull Via the Inbound Tailwind Test

(06:15) Trait #3: The Breakout Period Explained: Find the Risk-Reward Sweet Spot

(08:00) Trait #4: Does the Product Have a Path to Enterprise? The $100K Deal Question

(10:30) Trait #5: Why Actual Interest in the Industry and Problem is a Prerequisite to Sell Well

(11:30) Trait #6: Why Technical Sales Compounds Your Career

(13:30) Trait #7: The Ability to Do More Than Just Sell at an Early-Stage Startup

(15:00) Trait #8: Sales Leadership Must Be AI Native (and What That Actually Means)

(17:30) Trait #9: New York and/or SF Presence and the Case for the In-Person Feedback Loop

(19:45) Trait #10: The Engineering Team Needs to Be Shipping Constantly and How to Test Them

(21:30) Trait #11: Back Channel Everything: Who to Talk To and Who to Skip

(23:30) Recap of All 11 Traits & What's Coming Next on Vibescaling

About The Vibescaling Podcast

The Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.

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.

Where to Find Vibescaling

LinkedIn: https://www.linkedin.com/company/vibescaling/

YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg

Newsletter: https://www.vibescaling.blog/

Website: https://www.vibescaling.ai/

The Art & Science Of Choosing Which Startup To Join & How To Value Your Equity w/ Billy Gallagher, CEO @ Prospect Feb 24, 2026

Show notes

Billy’s Background

Billy Gallagher is the founder and CEO of Prospect, a robo-advisor that helps startup employees better manage their private company equity. Think: Wealthfront for startups.

Before Prospect, Billy was on the investing team at Khosla Ventures, where he worked on early-stage deals from seed through Series B, including companies like Stripe, DoorDash, and Instacart. He then joined Rippling as the 34th employee in a generalist "special projects" role, staying for three and a half years as the company scaled to over a thousand people. Between Khosla, Rippling, a Stanford MBA, and a stint covering startups at TechCrunch, he's seen the startup equity problem from literally every seat at the table

The gap he kept seeing between how professional investors managed equity at Khosla vs. how employees fumbled through it at Rippling is exactly what led him to start Prospect.

Timestamps

(00:00) Intro & Billy's path from Khosla Ventures to Rippling to founding Prospect

(03:44) How to evaluate a startup quantitatively: investors, headcount, web traffic

(05:14) Why the lead investor's seniority level matters more than the firm name

(07:14) Tracking investor quality across rounds (and when it's a red flag)

(09:17) The rise of the solo GP and what it signals for employees

(10:18) Second-time founders vs. first-time founders: when experience is an edge

(12:10) The Ramp example: hitting a double, staying hungry, then hitting a grand slam

(13:27) Tools for researching startups: Prospect, Crunchbase, and what to look for

(17:30) Headcount growth as a proxy for business growth

(19:54) Secondary market signals: what they tell you about a company between rounds

(22:14) When a fundraising gap is a red flag vs. a sign of capital efficiency

(24:46) The breakout period: why Series A–C is the best risk-adjusted time to join

(30:23) Qualitative signals: founder vision, speed, and the talent vortex

(32:07) How to spot a fast-moving founder without asking a single question

(34:00) Talking to customers: developing taste for product-market fit

(36:42) Market timing and the Paul Graham test: it should feel almost too late

(39:53) Equity 101: options vs. RSUs and when you'll get each

(41:50) QSBS and early exercise: the tax advantages most employees miss

(43:59) Post-termination exercise windows: why 90 days is no longer acceptable

(47:38) Percent ownership: how to benchmark your equity offer

(49:23)Tender offers and the 20% rule: taking chips off the table without losing upside

(52:24) What Prospect does and how to use it to navigate your equity lifecycle

About The Vibescaling Podcast

The Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.

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.

Where to Find Vibescaling

LinkedIn: https://www.linkedin.com/company/vibescaling/

YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg

Newsletter: https://www.vibescaling.blog/

Website: https://www.vibescaling.ai/

The Best Sales Reps Are Coin Operated & All Roads Lead Back To The Steak Dinner w/ Jack Gashi, VP of Sales @ Avoca Feb 17, 2026

Show notes

Jack's Background

Jack Gashi is VP of Sales at Avoca, an AI-native platform bringing automation to home service businesses. At Avoca, Jack is building the sales organization from scratch as the company scales AI-driven voice and scheduling technology across industries.

Before Avoca, Jack spent several years at Check, a high-growth cybersecurity startup, where he learned what it actually takes to build durable GTM teams. Prior to that, he worked in ad sales at Foursquare during the company’s peak growth years, and even earlier in his career Jack cut his teeth in classic boiler-room sales at Yext, making hundreds of cold calls a day selling into home services.

Through experience across SMB, mid-market, and enterprise sales, Jack knows what it actually takes to build a sales org that works. His philosophy is rep-first and unapologetic: sales is coin-operated, built on trust, and keeps the lights on. He’s a proud Jersey guy, a former Fyre Festival attendee (yes, really), and the first to admit that the best sales conversations still happen face-to-face.

Discussed In This Episode

• Why fear-based sales cultures break down while trust-first cultures actually scale

• Jack’s early career in boiler-room sales (150 cold calls a day) and why that foundation still matters

• How tech sales talent evolved from “falling into it” to Ivy League grads choosing it deliberately

• The “trough of disillusionment” every sales career hits

• Why sales is coin-operated and why pretending money doesn’t matter creates misalignment

• The hidden, spreadsheet-level cost of losing a $2M ARR top rep

• How to spot whether sales is a first-class citizen or a “necessary evil” at a company

• Why PLG works… until it doesn’t

• How real trust gets built (hint: it’s not five-step cadences)

• Why great AEs sell their own job search like a deal

• What sales skills transfer to real life

Timestamps

(00:00) Why fear-driven sales cultures fail — and what actually builds trust

(03:29) Fyre Festival and the danger of believing the outside story

(06:03) 150 cold calls a day at Yext and learning to really sell

(09:28) How tech sales talent has changed — Ivy League grads choosing sales

(15:03) The “trough of disillusionment” in a sales career

(18:19) Stop romanticizing work

(21:26) Sales morale as the beating heart of a company

(23:09) How to tell if a founder truly respects sales

(25:03) The real cost of losing a top rep

(26:11) “All roads lead back to steak dinners” — the limits of PLG

(29:00) Sales as trust transfer, not scripts

(31:02) Why automation and perfect sequencing keep failing

(33:04) Product knowledge as a trust weapon

(36:31) When to leave a good job — why Jack chose Avoca

(44:15) How elite AEs evaluate roles when data doesn’t exist

(46:06) Are the best reps coin-operated?

(53:41) What’s dead in modern sales

About The Vibescaling Podcast

The Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.

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.

Where to Find Vibescaling:

LinkedIn Company Page - https://www.linkedin.com/company/vibescaling/

YouTube -

https://www.youtube.com/@vibescaling

Newsletter -

https://www.vibescaling.blog/

Website -

https://www.vibescaling.ai/

The Words You Use Are Killing Your Trust & What Great Sellers Do Instead W/ Sam Berg, VP of Sales @ Tennr” Feb 10, 2026

Show notes

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.

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.

Where to Find Vibescaling

LinkedIn:

www.linkedin.com

YouTube:

YouTubeVibescaling Podcast

Newsletter:

Chris from vibescalingHome | Vibescaling Blog

Website:

https://www.vibescaling.ai/

Why You Should Join Cursor Over OpenAI and Anthropic & How To Avoid Bad Sales Hires W/ Tomer Chernia, VP of GTM @ Cursor Feb 03, 2026

Show notes

Tomer Chernia is the VP of GTM at Cursor, one of the fastest-growing companies in tech - reportedly going from 0 to $500M+ ARR faster than almost any company in history.

Before Cursor, Tomer spent three years at Vercel where he helped build out the go-to-market motion and developed their GTM efficiency framework. Prior to that, he was at Branch and Segment as early GTM hires.

Tomer got his start in tech at Yahoo, then joined Wildfire pre-acquisition by Google - where he caught the startup bug. He even tried his hand at founding a company before going back to sales.

He's a serious foodie (ask him for SF restaurant recs) and recently got into natural wine.

Discussed In This Episode

• His interview process evolution: from "pitch your product" to discovery sessions + deal reviews

• The "three hows" technique for testing candidate depth until their understanding breaks

• How Cursor went from 8 GTM people to nearly 100 in six months

• Why he chose Cursor over staying at Vercel (the "would you regret it?" test)

• The Cursor vs. OpenAI/Anthropic pitch for candidates - why "born adult" matters

• Why Cursor pays commissions when others don't - the real tradeoffs

• PLG sellers vs. top-down sellers - different strengths, different failure modes

• Why sales morale matters more than most leaders admit - and how quota setting destroys it

• "Buyers are liars" - why your champion isn't always a reliable narrator

• The future of outbound: signal-based, not spray-and-pray

Timestamps

(00:00) Intro & SF Restaurant Recommendations from a Serious Foodie

(04:00) From Humanities Major to Yahoo: How Tomer Fell Into Sales by Accident

(12:00) Wildfire, Google, Founding a Company & Why He Went Back to Sales

(20:00) The Tap on the Shoulder from Cursor: "Would You Regret Saying No?"

(26:00) How to Actually Hire Great Salespeople: Discovery Sessions + Deal Reviews

(32:00) The "Three Hows" - Testing Candidate Depth Until Understanding Breaks

(38:00) Why Sales Morale Matters: Quota Setting & Rep Motivation

(44:00) Cursor's GTM Growth: From 8 People to Nearly 100 in Six Months

(50:00) Why Cursor Over OpenAI or Anthropic: The "Born Adult" Company

(56:00) The Future of Outbound & How to Stand Out as a Candidate

About The Vibescaling Podcast

The Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.

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.

Where to Find Vibescaling:

LinkedIn Company Page -

https://www.linkedin.com/company/vibescaling/

YouTube -

https://www.youtube.com/@vibescaling

Newsletter -

https://www.vibescaling.blog/

Website -

https://www.vibescaling.ai/

Jack Dorsey Hired Me from My Dorm Room As Employee 100 @ Square | Mike Donahue, CRO @ Maven AGI Jan 28, 2026

Show notes

Episode Description:

Mike Donohue is the CRO at Maven AGI, one of the fastest-growing AI agent companies focused on customer support automation.

Before Maven, Mike was SVP of Sales at Gubshup, a messaging AI tool, and spent time at PayPal to give BigCo a spin.

He was an early sales hire at Lean Plum, growing with the company from Series A through Series D and competing head-to-head with Braze during the mobile marketing wars.

Mike's career started unconventionally - while captain of the varsity heavyweight rowing team at Columbia, he ran a dorm business doing room cleaning, dry cleaning, and beverage delivery.

He started using Square to process payments, fell in love with the product, and eventually got hired directly by Jack Dorsey when the company was sub-100 employees.

He's a Philly native who will tell you Tony Luke's beats Pat & Geno's as the best cheesesteak in Philly.

Discussed in this episode:

Why sales is a science, not an art - and why hiring "artists" at scale doesn't work
The interview question that reveals how candidates actually use AI: meh, good, and great answers
How Mike went from running a dorm business at Columbia to getting hired by Jack Dorsey at Square
The athlete mentality in sales and why "the score takes care of itself"
Where AI agents are actually delivering ROI in customer support today
The Braze vs. Lean Plum horse race: what competing from Series A to C taught him about GTM
Why sales dinners are dead and education-first selling is the new playbook
How to stand out when reaching out for a job (hint: it's not just a LinkedIn DM)
Why the best salespeople are building with AI tools like Claude and Windsurf, not just using ChatGPT for interview prep

Episode Timestamps:

(00:00) Intro & Best Philly Cheesesteak: Why Tony Luke's Beats Pat & Geno's

(04:00) Running a Dorm Business at Columbia & Discovering Square

(08:00) Getting Hired by Jack Dorsey When Square Was Sub-100 Employees

(12:00) The Athlete Mentality in Sales: "Score Takes Care of Itself"

(18:00) Why Sales is a Science, Not an Art - Playbooks Beat Artists

(24:00) How to Evaluate AI Usage in Sales Interviews: Meh, Good & Great Answers

(30:00) "I Vibe Coded 80% of My Outbound in Windsurf" - What Impresses Hiring Managers

(38:00) Where AI Agents Are Actually Working in Customer Support

(45:00) The Braze vs Lean Plum Horse Race: Competing from Series A to C

(52:00) Why Sales Dinners Are Dead & Education-First Selling is Winning

(58:00) Maven AGI is Hiring - What Mike Looks For in Candidates

About The Vibescaling Podcast:

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 & SaaS startups) 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, media, & investing firm for seed through series C AI-natives & fast-growing SaaS startups scaling from 0 to $100M ARR.

Where to Find VibeScaling:

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