The Crew Podcast (fka The Vibescaling Podcast)

Crew

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/

  1. 6d ago

    Why Product Love Doesn't Actually Close Deals w/ Simran Duggal, VP of Sales @ Juicebox

    Simran Duggal is VP of Sales at Juicebox, an AI-native recruiting platform where she leads GTM across three functions and 18 direct reports. She spent five years at Webflow as one of its early enterprise reps, building an enterprise motion on top of a product-led base, and came up before that in enterprise B2B SaaS. She got there by accident: a founder-track master's at Waterloo (Business, Entrepreneurship & Technology) put her in a room with brilliant early-stage technologists who had no idea how to commercialize, and she realized selling was the craft she wanted to build. In this conversation, she and Chris get into the learnings from scaling PLG into enterprise, the traits she screens for when hiring sellers in the AI era, and why the old sales playbooks no longer apply. Discussed in this episode: Why loving a product and buying it are two different things, and how a pipeline of fans inflates your forecastSelling to users vs. buyers, and to marketers vs. developersThe number one trait she screens sellers for: mental resiliencyHiring "spikes" over generalists to raise the whole team's ceilingScrapping the job title to hire in the AI-native eraThe mock discovery call and the feedback round that actually decides itWhy personalization is about the buyer's problem, not their alma mater, and why the phone call still convertsHow the best talent leaders are becoming business strategistsWhy she believes the universal sales playbook is dead Timestamps: (0:00) Background: from Waterloo's founder track to sales (4:34) Founder mistakes: conviction pointed the wrong way (5:31) Webflow: joining as an early enterprise rep (6:22) Two-engine companies: why she wanted PLG + sales (7:27) The downside of selling on a PLG base (10:30) User vs. buyer: what Webflow got wrong (11:57) Marketers vs. developers: the art of vision casting (15:46) Webflow as a GTM talent factory (19:28) Hiring spikes: elevate everybody, raise the bar (20:58) The number one trait: mental resiliency (23:18) The mock discovery call (24:52) The feedback round that decides it (27:14) Reading a career: running toward vs. away (28:42) Leaving Webflow, betting on AI-native (33:06) Why recruiting: the Juicebox thesis on people (40:24) Talent leaders as business strategists (43:33) Outbound that works: pick up the phone (46:24) The AI tools she can't work without (50:05) The sales advice Simran thinks is dead (51:42) How to actually get Simran’s attention 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: linkedin.com/company/crewgtm YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg Newsletter: withcrew.blog Website: withcrew.ai This episode is brought to you by Dust. AI has made individual GTM work faster. But it hasn't made GTM teams more coordinated. Too much work still happens in silos. One person, one agent, one threat at a time. Dust gives teams of humans and agents a shared workspace to move complex go-to-market work forward using the right model for the job. Think account command centers, RFP deal rooms, and cross-functional launches. Instead of keeping AI work trapped in threads, Dust makes agents part of how your team coordinates makes decisions and drives work. That's multiplayer AI, and that's Dust. Check it out at: https://dust.tt/

  2. Jul 14

    Don't Take the Anthropic Job First w/ Mark Goldberger, VP Sales @ Metaview

    New episode of the Crew Podcast with Mark Goldberger (VP of Sales at Meadowview, the AI-native recruiting platform). Mark's career is the dictionary definition of the non-obvious path: sommelier tasting 5,000 wines a year → bootstrapped a big-data startup in 2009 → 100 job applications with zero callbacks → founding enterprise hire at TripActions/Navan → two and a half years running enterprise at Ramp → now building GTM at Meadowview. Along the way, he brought in ~$100M in revenue for some of the most sought-after companies in tech. This one is for founders deciding when to invest in enterprise, VPs rethinking productivity metrics in the AI era, and reps with a weird résumé trying to break into a company that keeps ignoring their applications. Discussed in this episode: The 80/20 rule of sounding smart with a wine list (from a former somm who tasted 5,000 wines a year)Why breaking into SaaS with a non-traditional background is all about persistence, creativity, and finding an allyThe 1% move: candidates who learn the product and demo it back to youCompany selection as a concentrated VC bet: TAM, founders, and real customer loveWhy enterprise is a conviction test most companies fail at the 90-day markThe pricing tell: if you're only losing on price 10–15% of the time, you're too cheapLogos over margins early, and why ten enterprise logos beat the deal economicsThe MEDDPICC-as-activity method, and the rep who taught Claude to run itWhy in-person sales came back, and why the human is the differentiator when everyone has AIThe ten-second LinkedIn scan: trajectory, job-hopping, and builder DNABreaking in when you don't fit the rubric — earn your way up the mountain"No champion, no deal" applies to hiring as much as sellingToken-maxing vs doing more with lessTimestamps: (00:00) Cold open: the concentrated bet of company selection (03:10) Long Island roots and the wine-sales origin story (05:19) From wine to SaaS: the impetus to switch (06:56) 100 applications, zero callbacks: breaking in without the résumé (08:15) The 1% move: candidates who demo your product back to you (09:30) Company selection as a concentrated VC bet (11:02) What TripActions and Ramp got right: talent density and PMF (14:49) The 180-degree flip: selling SMB vs. enterprise (18:25) The pricing tell: how much resistance is too much (19:10) AI fluency in the field: the rep who taught Claude MEDDPICC (22:26) Pilot data → insights → a Lovable dashboard built by an AE (25:36) The $10M-per-rep quota myth vs. product-market fit (33:39) The ten-second LinkedIn scan: green flags and red flags (37:29) Earn your way up the mountain: double-A before the home runs (39:08) Non-obvious beats obvious: selling travel during a pandemic (41:09) What changes when you're hiring a leader vs. an AE (46:47) No champion, no deal: hiring works like a sales process (49:04) The top GTM teams in the SaaS and AI era (51:07) Favorite quotes: pressure is a privilege, job's not finished (52:52) The art of taking away: brevity in the AI era (55:26) What Meadowview does: agentic recruiting, sourcing, and application review 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/crewgtm/YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_KhrlxgNewsletter: https://www.withcrew.blog/Website: https://www.withcrew.ai/

  3. Jul 7

    How To Pick The Right AI Company To Bet On & Operationalize Champion Building w/ Bryan Cox, VP of Worldwide Sales @ Braintrust

    Bryan Cox is the VP of Worldwide Sales at Braintrust, the eval and observability platform that builders and frontier model providers alike rely on to ship AI agents. Before Braintrust, Bryan spent nearly five years at Grafana, joining at Series A/B and helping build one of the most respected go-to-market motions in developer tooling. Earlier in his career he cut his teeth selling complex cloud and data-center infrastructure, including a stint at Flexera, learning what large strategic "whale-hunting" deals look like in action. A former college tennis player and self-described history major who fell into sales, Bryan treats the work like the craft it is, and is moving his family from Santa Barbara to the Bay Area to get closer to the action. Timestamps: (00:00) Cold open: the one-click "no" that exploded a seven-figure deal (01:22) Welcome to the Crew podcast + sponsors (02:52) From early cloud computing to Flexera's whale-hunting deals (06:02) Why Grafana produced so much elite sales talent (07:23) Choosing Braintrust: going where the highest-value problem is (09:34) Job as craft: loving the technical, hard-to-understand sale (13:31) What separates great reps from good ones on enablement (14:35) Sales as an ultramarathon: balance, burnout, and your "why" (22:05) The motion offense: circling a deal instead of running waterfall (25:08) The seven-figure deal that died, and operationalizing champions (29:41) How to interview a company: TAM, durability, and who's buying (33:10) The 40-call diligence process before joining Braintrust (36:50) Why everyone's moving to voice agents for ramp and enablement (42:25) The AI tool stack and a hot take on too much DIY (44:21) Rapid fire: GTM teams he admires and what he tests for in hiring (46:47) "Why are you in sales?" and the Shrek/onion test (50:44) The most creative way to break into Braintrust (hint: it’s not through Bryan) 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/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Newsletter: https://www.withcrew.blog/ Website: https://www.withcrew.ai/ This episode is brought to you by the following sponsors: Dust AI has made individual GTM work faster. But it hasn't made GTM teams more coordinated. Too much work still happens in silos. One person, one agent, one threat at a time. Dust gives teams of humans and agents a shared workspace to move complex go-to-market work forward using the right model for the job. Think account command centers, RFP deal rooms, and cross-functional launches. Instead of keeping AI work trapped in threads, Dust makes agents part of how your team coordinates makes decisions and drives work. That's multiplayer AI, and that's Dust. Check it out at: https://dust.tt/ Centralize If you work complex enterprise deals, the hard part is an effort, it's visibility. Who we met with on this account? Who's gone quiet? Who's on my team who can open a door that we haven't knocked on yet? Centralize answers all three of those questions. It builds a live stakeholder map for every deal, pulling from Salesforce, email calls, and your team's networks and then telling you where to go next. Teams at LangChain, Decagon, Webflow, and Cognition run on it. Try it on a live deal now at usecentralize.com.

  4. Jul 4

    State of GTM Recruiting @ The AI-Natives w/ Chris Balestras, Co-founder @ Crew

    This week, Chris goes solo. No guest necessary as he shares his reaction to a recent 20VC episode where Chad Peets and Chris Degnan sat down with Harry Stebbings to lay out their view of the GTM recruiting landscape. The two dropped roughly 18 claims about hiring, comp, and what’s actually happening on the front lines. Chris breaks them all down one by one. The result is a state-of-the-union on go-to-market recruiting for anyone trying to land at a Series A through D AI-native company in New York or SF right now. As a co-founder of Crew and a former enterprise seller for seven years, Chris works with nearly every company in the market, and he uses that vantage point to separate the takes he agrees with from the ones he thinks miss the mark. Discussed In This Episode Why the “never hire from Salesforce” take is half right and half wrong, and the three risk vectors Chris actually screens forThe hidden difficulty of selling at a brand-name incumbent, and the real tell that should make you skeptical of a five-year Salesforce repWhy hiring out of security is its own puzzle, and the few orgs still running a hard, direct, technical saleThe clean benchmark Chris is “stealing” for his advising: $1.5M of productivity per rep as the line between hiring faster and overhiringWhy you should always set quotas slightly too low, and the morale death spiral when you set them too highWindfall clauses explained: why companies are capping payouts on $20–30M deals, and why it’s actually a good signWhy raising a huge round tells you almost nothing about whether it’s a good go-to-market opportunityThe forward-deployed engineer debate, and why Chris disagrees that it’s just glorified professional servicesWhy even great operators need an accountability partner, and the personal-trainer analogy for recruitersHow Anthropic is pulling the best reps out of the market, the de-risking logic driving it, and why it looks like Salesforce in 2001The Snowflake hiring mistake that may have let Databricks inflect past themWhy so much VC go-to-market advice is dangerous, and the operating experience most VCs are missingWhy cutting the bottom 10% every year is a fear-based McKinsey relic that doesn’t fit a winning orgEveryone is working harder than ever, and why staying enabled on AI now takes nights and weekendsThe $100M exec packages at the top, and the K-shaped split forming across the marketWhy seat-based pricing is dying, and what consumption means for top-down vs. usage-based sellersWhy industry expertise is overrated, the one exception Chris makes, and why a Rolodex hire is worst of all 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, and 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, and media firm for seed through series C AI-natives and fast-growing SaaS startups.

  5. Jun 30

    Sales Mafias & What Made MongoDB Great w/ Graham Moreno, VP Worldwide GTM @ Parallel

    Graham Moreno is the VP of Worldwide GTM at Parallel Web Systems, where he's building the go-to-market motion for one of the most talked-about AI-native companies in the space. Before Parallel, Graham scaled Windsurf's GTM org from a handful of sellers to a full enterprise machine, serving as President through the company's acquisition by Cognition. Earlier, he spent five years at Grafana Labs building and leading enterprise sales, and came up through the legendary MongoDB sales org, the "Mongo mafia" that's produced a remarkable share of today's best GTM leaders. He got his start, somewhat by accident, at Oracle straight out of college. He's a self-described enablement obsessive, a Delta loyalist, and a believer that the people you work with matter more than the product you're selling. 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/crewgtmYouTube: https://www.youtube.com/@thecrewgtmNewsletter: https://www.withcrew.blog/Website: https://www.withcrew.ai/ This episode is brought to you by the following sponsors: 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 Dust AI has made individual GTM work faster. But it hasn't made GTM teams more coordinated. Too much work still happens in silos. One person, one agent, one threat at a time. Dust gives teams of humans and agents a shared workspace to move complex go-to-market work forward using the right model for the job. Think account command centers, RFP deal rooms, and cross-functional launches. Instead of keeping AI work trapped in threads, Dust makes agents part of how your team coordinates makes decisions and drives work. That's multiplayer AI, and that's Dust. Check it out at: https://dust.tt/ Centralize If you work complex enterprise deals, the hard part is an effort, it's visibility. Who we met with on this account? Who's gone quiet? Who's on my team who can open a door that we haven't knocked on yet? Centralize answers all three of those questions. It builds a live stakeholder map for every deal, pulling from Salesforce, email calls, and your team's networks and then telling you where to go next. Teams at LangChain, Decagon, Webflow, and Cognition run on it. Try it on a live deal now at usecentralize.com.

  6. Jun 23

    How We're Building Granola Into the Most Beloved Product in AI w/ Bardia Shahali, VP Sales @ Granola

    Bardia Shahali is the VP of Sales at Granola, one of the most beloved products in tech right now, where he's turning a product people are obsessed with into a real enterprise GTM motion. He's spent his career betting early on the right companies. He learned to sell as an AE at BlackLine (which went public), moved to San Francisco for Intercom, then joined Teleport as its first sales hire at seed stage and helped take it from $0 to $20M ARR and a $1B valuation. In early 2024 he joined Fireworks at Series A and helped scale it, before landing at Granola. Along the way, he's advised a number of 0-to-1 companies building their first go-to-market engine. He met his wife at Intercom, sold his house and moved his family (plus two dogs) back to SF so he wouldn't miss the AI wave, and talks into Wispr Flow so much his wife says it's "what old people do." He's also a prolific writer on sales and GTM, and once got rejected from his dream MBA program and decided to go build startups instead. Timestamps(00:00) Intro(01:22) Welcome to the Crew Podcast + Sponsor(02:47) Granola: One of the Most Beloved Products in Tech(03:13) The Booth Rejection & Bardia's Career Arc(06:18) Moving Back to SF for the AI Wave(08:03) What Actually Makes Granola Special(10:31) Is the Entry-Level Sales Role Dead?(12:06) Killing the Busywork, Not the Job (Claude Co-Work)(18:29) Build Your GTM Org Around Your Sales Cycle(24:22) Why $100M ARR Doesn't Mean What It Used To(26:42) The Hiring Mistake That Wrecks AI Companies(32:38) The AI Tools Bardia Can't Live Without(35:34) The Steak Dinner Is Dead(40:13) How To Choose the Right Company in AI(45:23) Founder-Market Fit, Market Pull & TAM(48:10) Interviewing for Mindset Over Mechanics(49:39) The Outreach That Stood Out(52:10) The GTM Orgs Bardia Admires (Figma & Cursor)(54:11) The "Order Taker" Debate(57:27) Why 90% of AI Unicorns Are in SF(01:00:56) Granola's Roadmap & What's Next 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/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Newsletter: https://www.withcrew.blog/ Website: 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

  7. Jun 16

    How To Hire Sales Reps Like a Moneyball GM W/ Navid Zolfaghari, Chief Sales Officer @ Zapier

    Navid's Background Navid Zolfaghari is the Chief Sales Officer at Zapier, where he's leading the push to move one of PLG's most iconic companies up-market into the enterprise. Before Zapier, Navid spent six years at Branch, joining at roughly $500K in revenue and helping scale it to ~$100M. He then went to Metronome to go deeper on usage-based pricing. Early in his career, he was at a retail analytics startup and before that he co-founded a company focused on micro-location data and beacons. Navid got his start at Wildfire, which he joined at ~20 people and watched grow to 400 people before it was acquired by Google. He spent a couple of years at Google post-acquisition, which was plenty long enough to learn that the big-company lifestyle wasn't for him. He's also a poker player, a Miami Heat loyalist, and shamelessly pours his milk before cereal (yes, we think it’s crazy too). Timestamps (00:00) Intro & Why Navid Made the Trip from Redwood City (11:16) Navid's Background: Two-Time Founder to GTM Leader at Wildfire, Branch, Metronome & Zapier (13:07) The Google Acquisition Story & Knowing Big Company Life Wasn't for Him (15:00) What Zapier Actually Is Now: Agents, MCP & the Evolution Beyond Hand-Rolled Zaps (15:35) AI Fluency at Zapier: The Four-Tier Rubric & Why "I Use ChatGPT" Is Now Unacceptable (21:34) The War Council: An AI Advisory Board the Entire Exec Team Uses (23:38) How Zapier Fits Into the MCP & Claude Co-Work Era (34:43) Most Common Personas & the Rise of the "Head of AI Transformation" (36:22) The Unified Value System: How One AE Replaced an Entire Sales Value Engineering Function (38:36) Tools You'd Have to Rip From His Cold Dead Hands (42:03) The Blueprint for Excellence: Startup Fit, Business Athleticism & Purposeful Drive (53:57) Love to Win vs. Hate to Lose: How He Evaluates Competitive Drive (01:05:28) The Consultant Mindset: What's Actually Changed in the Sales Archetype 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 YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxghttps://www.youtube.com/@thecrewgtm Newsletter: https://www.vibescaling.blog/https://www.withcrew.blog/ Website: 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

  8. Jun 9

    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 YouTube: https://www.youtube.com/@thecrewgtm Newsletter: https://www.withcrew.blog/ Website: 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

Ratings & Reviews

5
out of 5
8 Ratings

About

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/

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