Village Global Podcast

Jeff Cobourn leads finance, business operations, and strategy at Gusto, where he's spent nearly nine years building out the company's financial infrastructure. Rohit Divate recently joined Tide as VP of Finance after seven years in corporate finance and strategy at Gusto.Somrat Niyogi, General Partner at Recall Capital and Village Global Network Investor, sits down with Jeff and Rohit to unpack how AI has rewired the finance function from the inside out. They trace the shift from spreadsheets and BI tools to Claude Code as the default daily workflow, including how board decks that once took two weeks and five people now come together as pull requests against an HTML file. The conversation moves through what finance skills and attributes still matter in an AI-native world, whether teams will shrink or simply cover more ground, and how roles like BI, investor relations, and data visualization are starting to merge. Jeff and Rohit also get into the practical mechanics of the shift: how Gusto scores AI fluency across the entire company, how they're budgeting for token spend the way they once budgeted for headcount, and where the real build-versus-buy tension is playing out across ERP, FP&A software, and internal tools. They close with predictions on what's dead, what's dying, and what the first hire at a finance team in 2026 should actually look like.Thanks for listening. If you like what you hear, please review us on your favorite podcast platform. Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal. Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

Sherwood Callaway is the founder and CEO of Sazabi, an AI-native observability platform, and a repeat YC founder. He previously worked as an early infrastructure engineer at Brex, where he built the systems that kept one of the fastest-growing fintechs in the world running.Village Global Luminary LP Lindsay Pettingill sits down with Sherwood for a conversation that moves from his unconventional path into engineering to the contrarian bets behind Sazabi. They dig into why Sherwood believes logs alone can replace metrics and traces, why dashboards mostly serve anxiety rather than insight, and what a world of self-healing software could actually look like. Along the way, Sherwood reflects on the 40-page manifesto that became Sazabi's founding thesis, the angel investor strategy that brought over 100 founders and technical leaders onto his cap table, and the maximalist, Blade Runner-inspired brand built around a name pulled from a 1980s anime. The episode closes on a more personal note, touching on his orthopedic surgeon father's late-career turn toward vibe coding and his sister Hadley's stint at Sazabi as its first non-technical hire before business school.Thanks for listening. If you like what you hear, please review us on your favorite podcast platform. Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal. Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

Moe Katib, founder and CEO of One and enterprise integrations expert, builds infrastructure to give AI agents authenticated, reliable access to apps. He discusses why trust matters more than speed or scale, the decision to open source integrations, running his email through an agent, and the identity and verification challenges that make agentic software fragile.

Alex Jekowsky, co-founder and CEO of Cents and Forbes 30 Under 30, built the software, hardware, and payments stack used by thousands of laundromats. He discusses breaking into a written-off market, winning customers with creative outreach and simple $299 pricing, scaling via distributors and an acquisition, and why agentic AI matters for small operators.

Reid Hoffman, co-founder of LinkedIn and venture investor who scales startups; Aaron Levie, Box CEO known for SaaS strategy and AI agents. They debate how agents can expand SaaS value and which software categories will rise or fall. They discuss whether models or platforms capture value, where startups should attack incumbents, and why enterprise adoption of AI is slower than hype suggests.

Somrat Niyogi sits down with two of the most experienced comms operators in tech: Kelly Boynton, Head of Communications at Gusto, and Paul Loeffler, former SVP of Communications and Brand at BILL.Kelly spent 15 years across agency and in-house roles before Gusto, including at Facebook, Instagram, Intuit, Navan, and DocuSign. Before BILL, Paul led integrated communications at Gusto and was at Atlassian pre-IPO, helping scale it as a public company.They cover what founders get wrong about launches and PR, when an agency is worth it (and when it is not), why your story should be about value rather than valuation, why reporters write about trends rather than companies, why 95% of stealth companies should not be in stealth, and the comms playbook for breaking through the noise.Thanks for listening. If you like what you hear, please review us on your favorite podcast platform.Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

Deon is the co-founder and CEO of Espa Labs. His previous company, Forethought, was a TechCrunch Disrupt winner in 2018, scaled to roughly a billion customer interactions a month, and was recently acquired by Zendesk, where Deon now serves as advisor.Village Global GP Anne Dwane sits down with Deon to talk about the launch and the journey that brought him here. They cover what he learned scaling Forethought through the GPT-1 to GPT-4 era, why the Iron Man Jarvis vision is finally within reach for everyone (not just Silicon Valley), the three pillars of Espa, why the model labs have perverse incentives that leave the door open for a new app-layer winner, the surprising network effect that emerges when one Espa starts talking to another, and where personal productivity AI is heading over the next five to ten years.Thanks for listening — if you like what you hear, please review us on your favorite podcast platform.Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

Jake Saper, General Partner at Emergence and developer of the AI-native services thesis, explains why many pre-AI SaaS firms are at risk. He discusses shifting from selling seats to selling outcomes. He covers disappearing and emerging moats, Mirage Product-Market Fit, the three metrics AINS founders should track, and where the biggest opportunities lie.

Nick Mehta, former CEO of Gainsight who led a $1.1B exit and helped define customer success. He recounts how cheap meetups and community-building birthed a category, selling into a role that barely existed, quirky early sales wins like the Box music-video deal, facing Salesforce staking claim, and the three pillars for creating a category: community, authority, and culture.

Dara Ladjevardian, CEO and cofounder of Delphi who builds interactive digital minds, reflects on recreating his grandfather’s mind with GPT-3 and why he chose LLMs. He discusses trust, avoiding clone culture, product pivots, scaling expertise, and a vision where digital minds amplify human presence while keeping people central.