Episodes

  • Fewer Reps, More Pipeline: How AI-Native GTM Teams Are Doing More With Less w/ Jason Miller, VP Sales @ Unify

    Fewer Reps, More Pipeline: How AI-Native GTM Teams Are Doing More With Less w/ Jason Miller, VP Sales @ Unify
    Apr 14 2026

    Jason Miller is the VP of Sales at Unify, a signal-based selling platform helping go-to-market teams connect buyer intent to personalized outreach at scale.


    Before Unify, Jason spent just over seven years at Monday.com, joining as one of the first 12 US sales hires when the company was almost entirely PLG and didn't even believe it needed a sales team. He helped build the outbound motion from the ground up, moved into sales leadership, and scaled the company through hypergrowth to IPO.


    Prior to Monday.com, Jason was at Convey (now project44), where he took over the founder-led sales playbook and built out the SDR and AE teams in the scrappiest of environments where you either learn fast or you don't last.


    He came up reading Predictable Revenue, built his career on the belief that inputs always drive outputs, and carries a clear philosophy into every org he joins: hire slow, keep the bar high, and don't confuse quota attainment with talent.


    Timestamps


    (00:00) Cold open: the Mount Rushmore of GTM signals(02:28) Jason's background: falling into sales and finding SaaS(05:30) What makes the Israeli tech scene different from SF and New York(09:35) Crossing the PLG chasm: why he left Monday for a sales-led company(10:19) Why he almost didn't join a go-to-market company (and what changed)(12:07) How to evaluate founders in an interview process(14:14) The dating analogy: finding the right sales culture fit(14:50) The hiring mistake that taught him never to lower the bar(16:52) How to prevent "shiny object" bias in an interview loop(18:56) What top candidates actually do differently (the follow-up problem)(20:24) Asking better questions: layers, active listening, and interview-as-discovery(22:23) The $1M growth hire and the future of the sales team(25:52) The sales tech landscape in 2026: how to cut through the noise(29:04) Ideal stack for a Series B AI-native: CRM, CI, sequencer, signals(30:53) Clay vs. Unify: how to think about using both(33:24) PLG vs. SLG: what really changes when the inbound stops(38:17) The three metrics every AE should track(39:46) Why quota attainment can be misleading(45:13) Cold outbound isn't dead (it just has to be better)(47:45) Roleplay, reps, and why HyperBound might be the most underrated tool(50:05) Methodologies that actually matter: MEDIC, MEDDPICC, Spiced


    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/
    Show More Show Less
    52 mins
  • How to Reinvent Yourself & The Athlete Mindset Behind Elite Sales Teams w/ Evan Cassidy @ Decagon

    How to Reinvent Yourself & The Athlete Mindset Behind Elite Sales Teams w/ Evan Cassidy @ Decagon
    Apr 7 2026

    Evan Cassidy’s Background

    Evan Cassidy is the VP of Sales at Decagon, the leading AI-native customer support platform. He joined as the company's first sales hire when it was doing less than $2M in ARR. Now? Decagon is valued at $4.5B, and Evan has been instrumental to scaling the GTM org along the way from a team of ten through Series A, B, C, and D.


    Before Decagon, Evan held sales leadership roles at Drift and Dropbox (after getting rejected the first time and doing a 10-month stint at Yelp to build his foundation) before reapplying and landing the role.


    Before getting into tech, Evan was a competitive rower: captain of Columbia's heavyweight team, two-time US Under-23 National Team member, and spent time at the Olympic Training Center in Oklahoma City.


    Evan had an unconventional start to his career after not starting full-time work until 25 that included driving across the country to San Francisco with no job, no plan, and not much money.

    His career has been a study in reinvention and in knowing when to throw yourself in the deep end.


    Timestamps


    (00:00) Intro & Evan's story: from rowing to Oklahoma City to San Francisco

    (06:16) Columbia's 100-year rebuild in 2 years and how that shapes Evan’s approach to team building today

    (11:22) What traits replace "former athlete" for candidates who didn't play college sports

    (15:17) Breaking into tech in 2013 and why Dropbox was the target

    (20:06) Getting rejected, going to Yelp, and coming back to get the job 10 months later

    (25:12) Why most people ruin their job search by skipping the inner work

    (28:45) The Never Search Alone approach and the feedback that redirected his career

    (33:00) What "feeling stuck" actually feels like and how one moment with an exec coach shifted things completely

    (40:50) Joining Decagon with a 2- and 3-year-old and under $2M in revenue

    (46:11) The AI bifurcation and why salespeople need to move now

    (51:37) What Decagon's GTM culture looks like and who is actually a good cultural fit

    (57:15) Building a magnetic organization: what it means, why it matters(01:01:30) Where customer support automation goes from here


    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/
    Show More Show Less
    59 mins
  • The $1M Salary GTM Role Nobody Qualifies For Yet w/ Jason Gelman, GTM Partner @ Primary VC

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

    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/
    Show More Show Less
    1 hr and 4 mins
  • How The Best CROs Actually Hire Salespeople w/ Kyle Norton, CRO @ Owner.com

    How The Best CROs Actually Hire Salespeople w/ Kyle Norton, CRO @ Owner.com
    Mar 24 2026
    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 moreTimestamps(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 StaffAbout 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 VibescalingVibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.Where to Find VibescalingLinkedIn: https://www.linkedin.com/company/vibescaling/YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_KhrlxgNewsletter: https://www.vibescaling.blog/Website: https://www.vibescaling.ai/
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    1 hr and 8 mins
  • My #1 Rep Closed $3.5M & Never Sold A Day In Their Life w/ Ghazi Masood, CRO @ Replit

    My #1 Rep Closed $3.5M & Never Sold A Day In Their Life w/ Ghazi Masood, CRO @ Replit
    Mar 17 2026
    Ghazi’s BackgroundGhazi 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 2025Timestamps(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 ListenAbout 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 VibescalingVibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.Where to Find VibescalingLinkedIn: https://www.linkedin.com/company/vibescaling/YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_KhrlxgNewsletter: https://www.vibescaling.blog/Website: https://www.vibescaling.ai/
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    49 mins
  • Why Anthropic is The Hottest Company in AI & & How To Use Claude As A Seller w/ Eleanor Dorfman, Head of Industries @ Anthropic

    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
    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 sellersTimestamps(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.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 VibescalingVibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.Where to Find VibescalingLinkedIn: https://www.linkedin.com/company/vibescaling/YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_KhrlxgNewsletter: https://www.vibescaling.blog/Website: https://www.vibescaling.ai/
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    57 mins
  • 11 Traits That Make A Hot Sales Job & How To Avoid Joining A Dud

    11 Traits That Make A Hot Sales Job & How To Avoid Joining A Dud
    Mar 3 2026
    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 limitsTimestamps(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 VibescalingAbout 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 VibescalingVibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.Where to Find VibescalingLinkedIn: https://www.linkedin.com/company/vibescaling/YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_KhrlxgNewsletter: https://www.vibescaling.blog/Website: https://www.vibescaling.ai/
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    23 mins
  • The Art & Science Of Choosing Which Startup To Join & How To Value Your Equity w/ Billy Gallagher, CEO @ Prospect

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

    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.


    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/
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    55 mins