Why 'Contrarian' Candidates Can Be Red Flags

In this episode of Run the Numbers, CJ Gustafson sits down with Sam Jacobs, Founder and CEO of Pavilion, the global community for GTM leaders. Sam shares how getting fired multiple times as a CRO led him to build a business rooted in belonging — one that monetized members first, prioritized intimacy over growth, and turned a Slack group into a multimillion-dollar company. He and CJ unpack the mechanics of community: the tradeoffs between exclusivity and expansion, why venture capital doesn’t always fit human-centered businesses, and how Pavilion balances pricing, curation, and access. They also explore the evolution of the GTM function — from the myth of the plug-and-play VP of Sales to how AI is reshaping RevOps, forecasting, and leadership. Finally, Sam reflects on building durable value beyond personal brand and what it really takes to scale trust as a product.

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LINKS:

Sam Jacobs on LinkedIn: https://www.linkedin.com/in/samfjacobs/

Company: https://www.joinpavilion.com/

CJ on X (@cjgustafson222): https://x.com/cjgustafson222

Mostly metrics: https://www.mostlymetrics.com

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TIMESTAMPS:

00:00:00 Preview and Intro

00:03:05 Sponsors – Mercury, RightRev, and Tipalti

00:06:50 Pavilion, Community, and Go-to-Market Leadership

00:10:28 Career Tenure and Executive Turnover

00:12:55 Compensation Structure and Equity Negotiation

00:14:31 Building Wealth Through Equity

00:16:30 Sponsors – Aleph, Fidelity Private Shares, and Metronome

00:19:36 Managing Wealth, Lifestyle, and Longevity in Leadership

00:22:58 Founding Pavilion to Empower Operators

00:25:13 Taking Roles for Learning, Titles, and Leverage

00:28:47 Contrarian Executives, Team Dynamics, and Leadership Lessons

00:30:36 What Makes a Great VP of Sales

00:33:23 Revenue, Profitability, and Misaligned Incentives

00:35:08 Quota Setting, Forecasting, and Spreadsheet Pitfalls

00:39:07 AI in Sales and the Myth of the AI SDR

00:40:32 The Future of Playbooks in the Age of AI

00:43:38 The Dangers of AI and the Need for Humans in the Loop

00:45:27 Monetizing Pavilion – Memberships, Sponsors, and Pricing Strategy

00:49:30 Building Higher-Margin Community Businesses

00:57:46 Building a Personal Brand with Long-Term Value

01:01:52 Closing Credits and Outro

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SPONSORS:

Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.com

RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.

Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.

Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run

Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

#RunTheNumbersPodcast #Finance #CommunityBuilding #Leadership #GoToMarket

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