How The Best Salespeople Are Building Agents in GTM w/ Roy Mathew, Head of Sales @ Gumloop

How The Best Salespeople Are Building Agents in GTM w/ Roy Mathew, Head of Sales @ Gumloop

Roy’s Background Roy Mathew is the Head of Sales at Gumloop, one of the leading AI agent builders helping companies automate workflows across sales, marketing, and IT. Before Gumloop, Roy spent several years at Airtable where he started as a growth lead, pitched the CEO to let him carry a bag, and helped build the sales playbook from scratch. After Airtable he followed his former head of sales to Recurrency, an ERP-adjacent platform selling into distributors and wholesalers. Before all of that, Roy was a special situations options trader, worked on the marketing team at Box, co-founded an automotive technology company called UQuote, and did a stint at Elastic. He's a Harvard undergrad, Wharton MBA, and has one of the more unconventional paths into sales leadership you'll hear. Timestamps: (00:00) Intro & The Sell-Grill-Sell Sandwich: Why Hiring Managers Kill Their Own Pipeline (02:39) Roy's First Call Horror Story: Getting Deal-Reviewed for a VP Role (04:55) From Options Trader to Box to Founding a Company: Roy's Roundabout Path Into Sales (09:47) Joining Airtable as Employee 25: How a Guy Looking Over His Shoulder Changed Everything (11:04) Pitching the CEO: "Let Me Carry the Bag or I'm Just the Spreadsheet Person" (14:46) How to Evaluate an Early-Stage Company: Beyond the Investor Logos (17:58) Why He Chose Gumloop: The Two-Week Interview That Threw His Framework Out the Window (20:17) MCP, Co-Work, and the Agent Era: A Non-Technical Explainer (26:06) The Blank Page Problem: How Gumloop Thinks About Personas vs. Use Cases vs. Industry (31:00) The Pre-Call Agent Stack: Email, Slack, Gong, Granola, and Web Scrapers in One Brief (35:34) The Post-Call Agent Stack: Recap Emails, CRM Updates, Linear Tickets, and Product Feedback (38:03) The Self-Improvement Loop: An Agent That Watches What You Actually Send (42:30) Agents for Sales Leaders: Process Adherence, Pipeline Inspection, and SPICED Monitoring (50:40) GTM Mafias: Why the Slack Mafia Might Be Overhyped (52:21) Blue-Chip-Only Resumes Are a Red Flag: "You Want Someone Dangerous at a Bad Company" (57:15) The Outbound Play That Actually Works: Gumball Machines and Speaking Like a Human (59:35) What Roy Looks For When Hiring at Gumloop Right Now About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew (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 Crew Crew is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups. Where to Find Crew LinkedIn: https://www.linkedin.com/company/vibescaling/https://www.linkedin.com/company/crewgtm [https://www.linkedin.com/company/vibescaling/https://www.linkedin.com/company/crewgtm] YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxghttps://www.youtube.com/@thecrewgtm [https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxghttps://www.youtube.com/@thecrewgtm] Newsletter: https://www.vibescaling.blog/https://www.withcrew.blog/ [https://www.vibescaling.blog/https://www.withcrew.blog/] Website: https://www.withcrew.ai/ [https://www.withcrew.ai/] This episode is brought to you by Salesgraph. Enterprise deals don't usually slip because of effort - they slip because the technical gap didn't get caught in time. A champion goes quiet, an objection never got handled, procurement shows up late. That context lives in your calls, Slack threads, and top reps' heads, and it doesn't transfer when you hire. Salesgraph pulls from your Salesforce, Gong, Granola, docs, and Slack, then writes the things that move deals forward - gap analyses, champion business cases, and pre-call briefs. It's like a company-specific GTM brain. YC-backed, built by founders who lived this at Mintlify. Get a free GTM audit → salesgraph.com/gtm-audit [http://salesgraph.com/gtm-audit]

Every Startup Is Lying to You, So Here's How to Pick the Right One w/ Glenn Rachlin

Glenn Rachlin is the VP of Worldwide Sales at Blockaid, a cybersecurity company protecting the blockchain and crypto ecosystem from malicious attacks. Before Blockaid, Glenn was an early sales hire at Alchemy, the infrastructure layer for crypto, where he helped grow the company from a $500M valuation to $10B and scaled the team from 10 to 130. Prior to his startup chapter, Glenn spent years at AWS during its era of dominance, where he experienced the wild "horse trading" culture of swapping accounts and reps between territories. He cut his teeth earlier at EMC (the classic 1980s sales org with Wolf of Wall Street energy) and IBM (old school, multi-generational, consulting DNA). Glenn is a Long Island native, a Bitcoin maxi who dollar-cost-averages into the ETF, a student of the Hunters and Unicorns podcast lineage, and a member of the Cyber Startups Network VC group. Timestamps (00:00) Intro (01:03) Glenn's Background: IBM → EMC → AWS → Alchemy → Blockaid (02:20) Why He Left AWS After Years at the World's Hottest Company (03:47) Cold-Calling CROs From Podcasts and Forcing Them to Be His Advisors (05:03) Getting Rejected by AWS Twice: The Loop Interview and What It Takes (06:53) Why Big-Company Reps Struggle at Startups (The Two-Sale Problem) (08:06) The "Order Taker" Debate: When Easy Mode Is Actually the Smart Move (09:58) Horse Trading at AWS: Swapping Accounts and Reps Like Sports Trades (12:07) Sales Orgs Glenn Admires Most: Scale AI, Wiz, Datadog, Snowflake (18:09) How to Choose the Right Startup: Founder Pedigree and Backchannel Everything (19:49) Every Startup Is a Complete Shit Show (And That's the Point) (25:28) Assessing Market Pull Before You Join (28:59) The Chainalysis Story: $100M to $8B Because of One Regulation (30:55) AI in Sales: Translating Hebrew in Slack and Vulnerability-Based Prospecting (32:35) Why Israeli Military Intelligence Breeds the Best Startup Founders (39:01) How AI Is Changing the Sales Profile and Quota Expectations (42:30) Why You Can't Hire Slow and Win(46:43) Glenn's Hot Take: If You Didn't Get the Job, You Didn't Try Hard Enough (50:15) What Doesn't Work in Sales Anymore: Remote Is Dying, Cold Calling Is Back (53:07) Bitcoin, Dollar-Cost Averaging, and Where Glenn Puts His Money (54:41) Creative Ways to Get in Front of Anyone (Without Being Weird) About The Crew PodcastThe Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew (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 CrewCrew is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups. Where to Find Crew LinkedIn: https://www.linkedin.com/company/vibescaling/https://www.linkedin.com/company/crewgtm [https://www.linkedin.com/company/vibescaling/https://www.linkedin.com/company/crewgtm] YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxghttps://www.youtube.com/@thecrewgtm [https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxghttps://www.youtube.com/@thecrewgtm] Newsletter: https://www.vibescaling.blog/https://www.withcrew.blog/ [https://www.vibescaling.blog/https://www.withcrew.blog/] Website: https://www.withcrew.ai/ [https://www.withcrew.ai/] This episode is brought to you by Salesgraph. Enterprise deals don't usually slip because of effort - they slip because the technical gap didn't get caught in time. A champion goes quiet, an objection never got handled, procurement shows up late. That context lives in your calls, Slack threads, and top reps' heads, and it doesn't transfer when you hire. Salesgraph pulls from your Salesforce, Gong, Granola, docs, and Slack, then writes the things that move deals forward - gap analyses, champion business cases, and pre-call briefs. It's like a company-specific GTM brain. YC-backed, built by founders who lived this at Mintlify. Get a free GTM audit → salesgraph.com/gtm-audit [http://salesgraph.com/gtm-audit]

How Harvey Scaled GTM to an 11B Valuation w/ Rob Saliterman, VP of Sales @ Harvey

Rob’s Background Rob Saliterman is the VP of Sales at Harvey, the AI platform for legal professionals that's grown from two customers to a $11B valuation in under two years. Before Harvey, Rob spent five years at Stripe leading teams focused on B2B vertical software platforms. Prior to that, he held sales and leadership roles at Snapchat and Google, where he got his start running political advertising sales after a career in government, including time in the White House. Rob got into sales through an unlikely door: Google needed someone who understood politics and could learn digital marketing. He'd never carried a bag before. He has an MBA from Harvard Business School and is one of the few people in AI sales leadership who came up through government and political communications rather than traditional SaaS. Discussed In This Episode Why he cold messaged Harvey's co-founder on LinkedIn after reading an OpenAI portfolio list (and how he got a reply) Hiring a VP of Sales before hiring AEs: why Harvey did it backwards on purpose The interview question that gives the most signal: "Walk me through a big deal: how you created it, converted the champion, and closed it" Selling to lawyers who've never bought software before and why testing for non-technical communication matters more than legal expertise No champion, no deal (except when it's worth it to slog through without one) Why pipe gen is a muscle memory sport and the first thing reps deprioritize when they shouldn't Personalizing demos using a lawyer's own public filings and why lawyers lean in when you give them something to argue with Hiring management consultants alongside AEs to solve the change management objection The managing partner test: why consistency and credibility matter more than polish How Harvey went from five PDFs you could ask questions about to a collaboration platform with 1,000+ customers Timestamps (00:00) Intro (07:45) Rob's Background: White House → Google → Snapchat → Stripe → Harvey (08:40) Why He Cold Messaged Harvey's Co-Founder on LinkedIn (10:24) The Moment He Knew Harvey Was Real: A Lawyer's Outside Counsel Test (12:37) Career Path: How a Government Background Translates to Sales (15:16) The Common Thread Across Google, Stripe, and Harvey: Selling Something New (17:14) Hiring a VP of Sales Before AEs: Why Harvey Did It Backwards (21:05) What Makes a Great Harvey AE: Selling to Non-Technical Buyers (27:18) How the Hiring Profile Changed From 10 Reps to 100 (29:59) Pipe Gen at Harvey: Why the Fundamentals Still Work (34:42) Why Pipe Gen Is the First Thing Reps Deprioritize (36:44) Personalizing Demos With a Lawyer's Own Public Filings (40:05) Rev Ops as an Early Hire: Why Harvey Built Infrastructure From Day One (44:34) No Champion, No Deal (Except When It's Worth Breaking That Rule) (49:49) Change Management as a Sales Differentiator (52:00) The Managing Partner Test: Consistency Over Polish (55:19) Where Harvey's Best AEs Actually Come From (58:32) The "Why Now" Interview Question That Separates Good From Great (01:00:00) Wrap + Where Harvey Is Headed About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew (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 Crew Crew is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups. Where to Find Crew LinkedIn: https://www.linkedin.com/company/vibescaling/ [https://www.linkedin.com/company/vibescaling/] YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg [https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg] Newsletter: https://www.withcrew.blog/ [https://www.withcrew.blog/] Website: https://www.withcrew.ai/ [https://www.withcrew.ai/]

Why The Best Sales Rep You Interview Is Probably Your Worst Hire with Mike Heller, Partner @ Floodgate

Mike’s Background Mike Heller is a Partner at Floodgate, one of the most respected seed-stage venture firms in Silicon Valley known for early bets on companies like Twitch, Lyft, and Twitter. Before Floodgate, Mike spent four and a half years at Clearbit where he joined as the first sales and marketing hire and helped grow the business from just over $1M to nearly $15M ARR. Prior to that, he was an early enterprise seller at Dropbox during the era when it was a "nearly impossible" sell, competing against free bundled solutions from Google and Microsoft while Box was building everything the enterprise buyer wanted. Mike got his start in Singapore running sales for a test prep business, then got pulled into Dropbox's experimental bottoms-up sales motion before it even had a name. After Clearbit he built a GTM advisory practice working with pre-PMF founders, which eventually led him to the investor seat at Floodgate. Discussed In This Episode Why the Dropbox enterprise sale was so hard and why that difficulty bred an elite generation of sellers The "smooth talker" trap: why the most impressive interview candidate is often your worst hire Why founders hire salespeople too early and what they're actually trying to solve The Jason Lemkin "hire two AEs" rule and when it's completely wrong How Mike grew Clearbit from ~$1M to ~$15M as the first GTM hire Why he stopped wanting to be a sales leader, and what he chased instead How giving free feedback on founder sales calls built his advisory business, deal flow, and investor career The two traits Floodgate looks for before writing a check: speed and "super learning" Why the Wayback Machine is an underrated founder diligence tool Where AI is actually showing up in sales and where it's still not touching the core of the job Timestamps (00:00) Intro (01:35) Mike's Background: Singapore → Dropbox → Clearbit → Floodgate (04:09) What Made the Dropbox Sales Culture So Elite (05:02) Why Selling Dropbox Enterprise Was "Nearly Impossible" (06:01) Leaving Dropbox: Choosing Clearbit Over Slack and Segment (09:58) Growing Clearbit From $1M to $15M as First GTM Hire (11:17) Why Mike Stopped Wanting to Be a Sales Leader (12:48) Building an Angel Investing and Advisory Career (14:37) Common Mistakes Founders Make on Discovery Calls (15:43) When Founders Should (and Shouldn't) Hire Their First AE (18:22) Why Hiring Too Early Creates Bad Revenue (20:22) From Advisory to Floodgate: Choosing the VC Path (25:39) Do Operators Make Better Investors? (27:56) The Two Traits That Matter Before Writing a Check: Speed + Super Learning (30:40) The Wayback Machine as a Founder Diligence Tool (32:15) AI in the Sales Tech Landscape: What's Real and What's Not (36:56) Career Advice: Stop Optimizing for Logos, Chase Energy (40:08) The "Smooth Talker" Trap in Sales Hiring (43:55) Should Founding AEs Get More Equity? (48:13) Why You Shouldn't Optimize Your Fundraise Around a GTM-Focused VC (50:19) The Future of Sales: Reps Who Can Ship Code 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/ [https://www.linkedin.com/company/vibescaling/] YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg [https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg] Newsletter: https://www.vibescaling.blog/ [https://www.vibescaling.blog/] Website: https://www.vibescaling.ai/ [https://www.vibescaling.ai/]

How We Built Profound’s GTM Motion To A $1B+ Valuation w/ Mark Ebert, SVP of Revenue @ Profound

Mark’s Background Mark Ebert is SVP of Revenue at Profound, the answer engine optimization platform helping brands win in the new world of AI search. Before Profound, Mark spent nearly nine years at 6sense, joining to build out the East Coast sales team. After an eventful day one, including one AE quitting and the remaining one begging him to stay, Mark went on to help build the company into the ABM category leader. Before 6sense, Mark sold and led enterprise teams at Responsys / Oracle Marketing Cloud during the marketing cloud wars against Salesforce and Adobe. He started his career as a BDR at Experian right out of college, after his dad’s sage advice that since he wasn't going to be a doctor or a banker, he should find a way to get into sales. Mark is based in Boston, a history buff with a soft spot for Revolutionary War battle planning, and probably the most relentlessly optimistic sales leader you'll meet. Discussed In This Episode Why enablement teams shouldn't actually be running enablement and who should instead when product ships daily The two questions every new AE at an AI-native company should be obsessed with answering in week one The "leave them alone on the sales floor" test for spotting a sales leader who's actually a doer vs. a dashboard leader Why he'd rather hire the rep who crushed it at the #3 product company than the rep who hit 150% at the obvious category leader What World War 2 battle planning teaches him about running a POC The "see the movie before it plays" framework and how the best reps whiteboard the 3 most likely deal paths and pre-plan their counter-moves Why the B2B sales funnel is collapsing inside of LLMs (and the data on what 80% of buyers do after they leave ChatGPT) Marketing to your new "ultra customer": the LLM itself The Jolt Effect: why most deals die from fear of screwing up, not fear of cost and how to surface that fear before the buyer does AI tooling the team is leaning on right now (Dust, Granola) and how Mark uses an AI sales bot to grade his team's first calls overnight Timestamps: (00:00) Intro, What Profound Is Building & Why Mark Joined (02:14) From Experian BDR to Oracle Marketing Cloud: Why Mark Left for Sixth Sense (07:36) Why Your Enablement Team Shouldn't Run Enablement (13:38) The Two Questions Every New AE Should Obsess Over in Week One (17:05) The Sales Leader Who Won't Sell Is a Liability: The "Leave Them on the Sales Floor" Test (22:21) The 3-Path Whiteboard: How Great Reps See the Deal Before It Plays (23:24) Confidence vs. Overconfidence: The Hire Mark Worries About (27:09) What World War 2 Teaches Mark About Running B2B Evaluations (29:36) Why Hiring from the #3 Product Beats Hiring from the Category Leader (31:30) The Quota Attainment Question Most Hiring Leaders Read Wrong (33:30) The B2B Funnel Is Collapsing Inside ChatGPT (37:31) Marketing to Your New "Ultra Customer": The LLM Itself (38:38) Rapid Fire: Staying Upbeat, Dust, Granola & The Jolt Effect 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/ [https://www.linkedin.com/company/vibescaling/] YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg [https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg] Newsletter: https://www.vibescaling.blog/ [https://www.vibescaling.blog/] Website: https://www.vibescaling.ai/ [https://www.vibescaling.ai/]