2D AGO

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

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. 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 Company Page - https://www.linkedin.com/company/vibescaling/ YouTube - https://www.youtube.com/@vibescaling Newsletter - https://www.vibescaling.blog/ Website - https://www.vibescaling.ai/

1h 5m

FEB 10

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

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. Where to Find Vibescaling LinkedIn: www.linkedin.com YouTube: YouTubeVibescaling Podcast Newsletter: Chris from vibescalingHome | Vibescaling Blog Website: https://www.vibescaling.ai/

1h 6m

FEB 3

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

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. 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 Company Page - https://www.linkedin.com/company/vibescaling/ YouTube - https://www.youtube.com/@vibescaling Newsletter - https://www.vibescaling.blog/ Website - https://www.vibescaling.ai/

58 min

JAN 28

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

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 workThe interview question that reveals how candidates actually use AI: meh, good, and great answersHow Mike went from running a dorm business at Columbia to getting hired by Jack Dorsey at SquareThe athlete mentality in sales and why "the score takes care of itself"Where AI agents are actually delivering ROI in customer support todayThe Braze vs. Lean Plum horse race: what competing from Series A to C taught him about GTMWhy sales dinners are dead and education-first selling is the new playbookHow 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: ⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn Company Page⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Newsletter

1h 1m

JAN 22

How I Built Legora's GTM Motion To A $1B+ Valuation w/ Patrick Forquer, SVP Global Revenue @ Legora

Episode Description: Patrick Forquer is the SVP of Global Revenue at Legora, one of the leading players in the AI-native legal tech space, coming off a recent Series C raise to value the company at over a billion dollars. Before Legora, Patrick spent 7 years at Braze (formerly AppBoy) from the early days through IPO, leaving as the AVP of sales. He started his career as a BDR at Yext during the 2008 financial crisis, worked at Intralinks, then moved to Cloud Sherpas, managing their Google Cloud relationship before the Accenture acquisition. He was also CRO at Jacquard, an early generative AI company. Pat is one of the more down-to-earth people I've met in the space; I really enjoyed the conversation + hope you do too. Discussed in this episode: Why selling AI is fundamentally different than selling SaaSThe "last mile problem" in vertical AI and why deployment is where deals are won or lostHow deal velocity has accelerated - buyers are moving faster and expect sellers to keep upWhy MEDDICC is not a sales process and how discovery has evolvedThe false tension between PLG and enterprise salesWhat Chris Degnan's book "Make It Snow" reveals about Snowflake's counterintuitive GTM & why they admire itWhy the best time to be a seller is right nowEpisode Timestamps: (00:00) Intro & Pat's Background (02:30) Meeting His Wife at Memory Motel in Montauk (04:30) His Path: From BDR at Yext to SVP of Global Revenue at Legora (06:50) Selling SaaS vs AI: Why It's the Best Time to Be a Seller (12:00) The Last Mile Problem in Vertical AI Sales (18:00) How Deal Velocity Has Changed with AI (26:00) Discovery, Change Management & Why MEDDICC Isn't a Sales Process (34:00) Chris Degnan's "Make It Snow" and Snowflake's GTM Playbook (42:00) PLG vs Enterprise: The False Tension (55:00) Basketball Talk: Jalen Brunson, the Knicks & NYC Sports (58:00) Creative Ways to Break Through & Get a Response 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: ⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn Company Page⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠Newsletter

1h 2m

JAN 15

How I Broke Into VC From Sales With Liam Mulcahy, Operating Partner @ Kleiner Perkins

Episode Description: Liam Mulcahy is an Operating Partner at Kleiner Perkins, where he leads go-to-market strategy for their portfolio companies from Series A through C. Before Kleiner, Liam was an early member of the GTM ops team at Unusual Ventures where he served as the first sales rep for 26+ portfolio companies simultaneously, building their GTM motions from zero. He cut his teeth at MongoDB pre and post-IPO, where he went from being told "we don't think you can cut it" to becoming a top performer and sales leader. Liam is one of the most thoughtful and intelligent voices on zero-to-one sales, career strategy, and what it actually takes to break into venture capital from an operating background. Discussed in this episode: The cardboard cutout Hail Mary that landed Liam his job at MongoDBWhy you should treat interviewing like a sales dealThe "MBA in sales" - why MongoDB's training was more valuable than business schoolCold calling the Midas List to break into VC without an MBAHow Kleiner Perkins rebuilt their operating team with peak-career subject matter expertsWhy a signed contract is now your best competitive differentiatorThe three rings of outbound: warm network, lukewarm, and ice coldStep-by-step guide to breaking into VC from a sales background"Effort is free" - why some people are stuck in third gearWhat Liam would tell someone who says "I want your job" & how to break into VC from salesEpisode Timestamps: (00:00) Liam's Journey: From D1 Track Athlete to Kleiner Perkins Operating Partner (06:00) Why Advertising Taught Him Sales (Without Realizing It) (10:00) The Tim Ferriss Books That Sparked the Startup Bug (14:00) What Made MongoDB's Interview Process Hard (In A Good Way) (18:00) The Cardboard Cutout That Changed Everything (24:00) Treat Your Interview Like a Deal: Getting Feedback After Rejection (31:00) Dealing With Imposter Syndrome (36:00) "If You're Going to Do Something, Do It Well" - The Flashcard QBR Story (40:00) Why Liam Didn't Want to Be a CRO (45:00) Cold Calling the Midas List to Break Into VC (50:00) How Kleiner Uniquely Positions The VC Operating Model (57:00) Why a Signed Contract is Your Best Competitive Moat (62:00) How to Actually Break Into VC (Step by Step) 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: ⁠⁠⁠Website⁠⁠⁠⁠⁠⁠LinkedIn Company Page⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠Newsletter

1h 9m

JAN 8

From $2M to $950M ARR: How Kyle Parrish Built Figma's Sales Machine - Vibescaling Podcast Episode #3

Episode Description: Kyle Parrish was the third sales hire at Dropbox and the founding sales leader at Figma, where he scaled the business from $2M to $950M in ARR over six and a half years through their IPO. Before Figma, Kyle opened Dropbox's Austin office and hired 150 people in under two years. He's now advising and investing in top AI-native startups. Kyle is one of the most thoughtful go-to-market leaders in the game - his frameworks on PLG-to-enterprise, founder-led sales, and building high-performing teams are pure gold. Also, shout out to our awesome sponsor for this episode, Kondo. Think of it like Superhuman for LinkedIn messages - if you're terminally on LinkedIn like I am and your inbox is becoming unwieldy, give it a try for the first month free using this link - it saves me over an hour a day. Discussed in this episode: How Kyle spotted Figma before anyone else: the three trends that signaled a breakoutWhy PLG companies should consider hiring top-down enterprise sellers, and sometimes not "PLG sellers"The real reason early customers buy: they're betting on the founder and the dream, not the productWhen founders should hire a head of sales vs. starting with individual repsOpening Dropbox Austin: hiring 150 people in under two years and building the GTM hub from scratchThe founder-led sales trap: why pitching too early kills deals"Stay low at the highs, high at the lows": how to survive the emotional roller coaster of startupsWhat most founders get wrong about discovery (and why three boilerplate questions won't cut it)Building your network like a bonsai tree: intentional cultivation over years, not transactional asksWhy the best early-stage sellers are "evangelical" - and what that actually looks likeThe FOMO trap: why comparing yourself to companies on a sugar high will wreck youWhat Kyle would tell his younger self after 15 years in startups: stress out less, the score takes care of itselfEpisode Timestamps: (00:00) Kyle's Journey: From Dropbox's Third Sales Hire to Figma's Sales Leader (06:00) When Should Founders Hire Their First Head of Sales? (12:00) The Hardest Part of Founder-Led Sales Transition (18:00) PLG to Enterprise: Why You Might Want the Top-Down Seller (24:00) Building Dropbox Austin: 150 Hires in Under 2 Years (30:00) How Kyle Spotted Figma Before Anyone Else (The 3 Trends) (36:00) Scaling Figma from $2M to $950M ARR (42:00) "Stay Low at the Highs, High at the Lows" - Surviving the Roller Coaster (48:00) Why Founders Pitch Too Early (The Discovery Trap) (53:00) What Kyle Would Tell His Younger Self 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: ⁠⁠Website⁠⁠⁠⁠LinkedIn Company Page⁠⁠⁠⁠YouTube⁠⁠⁠⁠Newsletter

59 min

12/18/2025

This Week In GTM Episode #2 (Featuring Brendan Short of The Signal) - 12/5/25

Timestamps: (00:00) Intros (04:00) Vercel's AI SDR: Replacing a 10-Person Team with One GTM Engineer (08:00) When Should Founders Hire Their First Salesperson (11:00) "Sales Teams Should Be Indistinguishable from Product Managers" (14:00) What Does "Consultative Selling" Actually Mean? (18:00) The YC Founder GTM Playbook: LinkedIn-First Outbound (20:00) Why LinkedIn Content Beats Cold Email (26:00) Network-Led Growth: Why Warm Intros Still Win (30:00) "Climbing Cringe Mountain" - Why Posting on LinkedIn Works (34:00) Content as a Recruiting Superpower (38:00) Why Is Everyone Calling Sales "GTM" Now? (44:00) Ramp Shut Down Their Outbound Automation Team - Here's Why Episode Description: In this episode of "This Week in GTM," Chris, Cailen, and special guest Brendan Short (The Signal newsletter) break down the tweets they've been texting each other all week and share unfiltered takes on the evolving state of go-to-market. Discussed in this episode: Vercel's viral AI SDR story: why context matters (ACV, target accounts, and what actually scales)The new playbook for when founders should hire their first salesperson Why Stripe and Dropbox hired salespeople who "didn't feel salesy" - and what that actually meansThe death of cold email and the rise of LinkedIn-first outboundHow Brendan landed Slack and Notion as customers through content alone Network-led growth: why your investors and advisors should be your first pipeline source"Everything good is on the other side of cringe" - why founders need to postThe "GTM" rebrand of sales: status play or legitimate evolution?Why Ramp shut down their Outbound Automation Team and what comes nextContent as a recruiting superpower Host Links: Cailen DSa Chris Balestras Brendan Short About 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 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 Company Page - ⁠ / vibescaling ⁠ YouTube - ⁠ / @vibescaling ⁠ Newsletter - GTMBA - ⁠https://www.gtmba.ai/ Website - ⁠https://www.vibescaling.ai/

51 min

12/10/2025

This Week In GTM Episode #1 - 11/27/25

Timestamps: (00:00) Why We Changed Our Name from T2D3 to VibeScaling (12:00) Why Is Everyone Calling Sales "GTM" Now? (17:00) Is Sales an Art or a Science? (22:30) The Viral Giga Story: What to Look For Before Joining a Startup (33:00) How to Evaluate Startup Equity (Shares Outstanding Explained) (35:00) The AI Tools We're Actually Using Right Now (44:00) "Choose Company Over Title" - Is This Advice Actually Useful? (50:00) Easy Mode vs. Hard Mode: The Stripe 250M ARR Debate (55:00) Nepotism in AI Hiring: Why Who You Know Still Matters (57:00) Thanksgiving Food Power Rankings Episode Description: In the inaugural episode of "This Week in GTM," Chris and Cailen riff on the tweets they've been texting each other all week and share unfiltered takes on the state of early-stage sales. Discussed in this episode: Why we rebranded from T2D3 to VibeScaling (and why the old name stopped making sense in AI)The "GTM" rebrand of sales: pretentious or practical?How to evaluate a startup before joining: the science of de-risking your next roleWhy you need to know shares outstanding before accepting an offerThe AI tools we're actually using daily: Gemini, Clay, Nerve, Centralize, GammaMaggie from OpenAI's viral advice and why we push back on "choose company over title"Easy mode vs. hard mode: why joining at $250M ARR is fundamentally different than $0-5MWhy PLG sellers are "picking up money off the floor" and some admit their skills are atrophyingThe uncomfortable truth about nepotism in AI hiringWho you know still matters more than being qualified Host Links: Cailen DSa - LinkedIn - https://www.linkedin.com/in/cailen/ Chris Balestras - LinkedIn - https://www.linkedin.com/in/balestras/ About 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 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 Company Page - / vibescaling YouTube - / @vibescaling Newsletter - GTMBA - https://gtmba.beehiiv.com/ Website - https://www.vibescaling.ai/

1h 2m

12/03/2025

Episode 2: Raphael Parker, CRO @ Mandolin | How He Built Segment's GTM Engine from 0 to $100M

Episode Description: Raph Parker is Head of Revenue at Mandolin, an AI company transforming healthcare operations. Before Mandolin, Raph was the first go-to-market hire at Segment, helping scale the company from seed to its $3.2B acquisition by Twilio. He then served as Chief Growth Officer at New Front Insurance, taking another company from seed to unicorn (with an IPO likely on the horizon). He started his career as a corporate lawyer, then biked around the world for 2 years before stumbling into tech sales. He joined us to talk about the psychology of early-stage selling, how to create social proof when nobody knows you, what to look for in a CEO, and why you should compete at the shallow end of the gene pool. Also, shout out to our awesome sponsors for this episode, Kondo. Think of it like Superhuman for LinkedIn messages - if you're on LinkedIn like I am and your inbox is becoming unwieldy, give it a try for the first month free using this link - it saves me over an hour a day. Discussed in this episode: The three types of founders who start companies - and why you want to find the third bucketWhy "strong ideas, lightly held" is a critical trait in early-stage leadersThe three things you're optimizing for in your career: cash, equity, or career/talent developmentProspect theory for salespeople: how people make decisions on risk vs. reward (and why being rationally beneficial isn't enough)The real motivation behind every buyer: people just want to get promotedHow to use informational asymmetry to "hack" social proof when you only have two customersFlipping the script to start a sales callTurning the intro into something that works in your favor: the "I bet my career on this" framingWhy nobody believes a case study & what to do insteadWhy prospects open up when they realize you talk to way more of their peers than they doPMF in AI is obvious right now - here's what to look for instead"Compete at the shallow end of the gene pool": why the least sexy industries offer the biggest opportunities Episode Highlights: (00:00) From Big Law to BDR: Raph's Unconventional Path into Sales (09:00) How to Evaluate CEOs: The Three Types of Founders (18:00) Prospect Theory: Why Early-Stage Selling is About Risk, Not Features (24:00) Creating Social Proof When You Only Have Two Customers (29:00) The Sales Call Hack: Flipping Informational Asymmetry (33:00) The "Bet My Career On It" Intro That Changes Everything (36:00) Why Nobody Believes Case Studies (And What Prospects Actually Want) (42:00) Hiring Early Sales Reps: The First Class to Greyhound Test (50:00) Distribution vs. Product: Why Great Ideas Fail (58:00) Compete at the Shallow End of the Gene Pool About 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 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 scaling from 0 to $100M ARR. Where to Find VibeScaling: ⁠Website⁠⁠LinkedIn Company Page⁠⁠YouTube⁠⁠Newsletter - GTMBA

1h 6m

10/30/2025

Episode 1: Todd Busler, CEO @ Champify | The 0-1 Sales Playbook & GTM Career Guide

Episode Description: Todd Busler is the CEO of Champify, a sales intelligence platform helping teams build pipeline through champion and user tracking. Before Champify, Todd was a founding AE at Heap, scaling the company from $300K to $40M in ARR over six years. He started his career as one of the first 10 sellers at Square after working as a sales engineer at SAP, and spent time in venture capital at Unusual Ventures leading go-to-market operations. He joined us to talk all things 0 to 1 sales, how to choose your next GTM opp, the pros/cons of VC vs. operator, and plenty of other topics that touch on the intersection of GTM + AI + startups. Discussed in this episode: How to stand out when applying to hot startupsWhy sales engineers might be the better starting point than BDR roles in the AI eraThe two criteria Todd used to pick every companyLearning from mentors without working for themThe real reasons to transition from operator to VC (and why Todd went back to operating)Why templated SDR cadences are dead and how email is becoming "low-cost advertising"The split in modern sales: nerdy clay users running scaled campaigns vs. reps doing highly personalized creative workWhat curiosity actually means in sales interviews The two flavors of curiosity that predict sales success: understanding the competitive landscape + learning business economicsWhat books/podcasts Chris & Todd are reading/listening toHow to be intentional about "what game you want to play" in your career Episode Highlights: (00:00) Standing Out: How to Get Hired at Hot Startups (09:00) Navigating Career Decisions with Intention (18:09) The Transition to Venture Capital at Unusual (26:47) The Future of Sales: AI, Personalization, and Dead Tactics (29:54) Exploring the Path from VC Back to Operating (32:32) The Challenges of 0-1 Sales and Building Pipeline (34:56) Building Champify: Product Insights and GTM Strategy (39:28) Effective Strategies for Booking Meetings in 2025 (42:17) Leveraging AI in Modern Sales Organizations (53:58) Personal Growth, Community, and Tribe Mentality in Business About 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 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. About VibeScaling: VibeScaling is an advisory, recruiting, investing, & media firm for seed through series D AI-natives scaling from 0 to $100M ARR. Where to Find VibeScaling: WebsiteLinkedIn Company PageYouTubeNewsletter - GTMBA

56 min

Vibescaling Podcast

Episodes

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

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

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

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

How I Built Legora's GTM Motion To A $1B+ Valuation w/ Patrick Forquer, SVP Global Revenue @ Legora

How I Broke Into VC From Sales With Liam Mulcahy, Operating Partner @ Kleiner Perkins

From $2M to $950M ARR: How Kyle Parrish Built Figma's Sales Machine - Vibescaling Podcast Episode #3

This Week In GTM Episode #2 (Featuring Brendan Short of The Signal) - 12/5/25

This Week In GTM Episode #1 - 11/27/25

Episode 2: Raphael Parker, CRO @ Mandolin | How He Built Segment's GTM Engine from 0 to $100M

Episode 1: Todd Busler, CEO @ Champify | The 0-1 Sales Playbook & GTM Career Guide

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