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Welcome to another episode of Outlier Briefings. Marty Kausas, CEO and co-founder of Pylon, joins Merritt Hummer, Partner at Bain Capital Ventures to discuss how Pylon is taking on Zendesk, why B2B customer support is fundamentally different from B2C, and what it really means to build an AI-first company from day one. Pylon is competing against companies 100x its size, and this conversation is packed with practical lessons for founders, SaaS operators, and anyone building in AI or B2B. Timestamps: 00:00 – The Loneliness of Startup Founders 00:38 – Meet Pylon: The AI Customer Support Platform for B2B 01:08 – From Airbnb Engineer to Startup Founder 01:19 – Competing With Zendesk: Entering a Crowded SaaS Market 01:38 – The Multi-Product Strategy That Won Over Investors 02:37 – The Future of B2B Support: Conversational & Multifunctional 03:03 - The CEO Trek & AI-Native Culture 03:54 – Building the “Zendesk Killer” With Startup Speed 04:40 - “Happy Grinders” - Speed as a Startup’s Only Advantage 05:20 – 1,500 Customers, $51M Raised — And Still Grinding __ Website: BCV: https://baincapitalventures.com/ Pylon: https://www.usepylon.com/ __ X: Marty Kausas: https://x.com/marty_kausas Pylon: https://x.com/usepylon Merritt Hummer: https://x.com/merritthummer Bain Capital Ventures: https://x.com/BainCapVC __ LinkedIn: Marty Kausas: / martykausas Pylon: / usepylon Merritt Hummer: / merritt-hummer-aa187712 Bain Capital Ventures: / bain-capital-ventures