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

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 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/crewgtm [https://www.linkedin.com/company/crewgtm] YouTube: https://www.youtube.com/@thecrewgtm [https://www.youtube.com/@thecrewgtm] Newsletter: https://www.withcrew.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 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 [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 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/@thecrewgtm [https://www.youtube.com/@thecrewgtm] Newsletter: https://www.withcrew.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/]