Ep 25: 2 Co-Founders, 5 Dead Ideas, Then Pylon w/ Marty Kausas, CEO @ Pylon

For 40 years, the safe bet in enterprise software was Zendesk or Salesforce. Marty Kausas, founder of Pylon, thinks picking either for customer support today might now get you fired.

Before Pylon worked, Marty spent 2 years cycling through 2 co-founder breakups and 5 dead ideas. Today, Pylon has 5x'd revenue two years running, raised a $31M Series B from a16z and Bain Capital, and migrated 150+ customers off legacy support platforms. We cover the "happy grinder" culture, why B2B support is a completely different problem than consumer, the per-seat vs outcome pricing debate, and why Marty thinks buying Zendesk is now the risky move.

This episode is brought to you by Stifel Bank — trusted banking and venture debt partner for Sierra Ventures' portfolio. Learn more at stifel.com.

Chapters:(0:00) Cold open and intro(2:02) Meet Marty and Pylon(3:06) Co-founder breakups and 5 dead ideas(10:13) Salesforce → Support Force(13:29) LinkedIn as 80% of Pylon's pipeline(22:05) Why B2B support isn't ticket deflection(28:33) Not Sierra, not Decagon(32:34) The context layer(39:34) Shipping 40% faster as a compound startup(55:12) Why you might get fired for buying Zendesk

Where to find Marty Kausas:- LinkedIn: linkedin.com/in/mkausas- Pylon: usepylon.com