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Milin Desai is the CEO at Sentry, an application monitoring tool for developers. Sentry has recently passed two key milestones: 100K customers and over $100M in ARR. Before Sentry, Milin was a GM at VMware and scaled their cloud networking into a billion-dollar business. Prior to stepping into leadership roles, Milin was a PM at Riverbed and a software engineer at Veritas. — In today’s episode, we discuss: • The key ingredients of Sentry’s success • Sentry’s developer-centric approach • Lessons on pricing, packaging, and product from VMware • Being an external CEO at a startup • Forging successful relationships with founders — Referenced: • Building for the Fortune 500,000: https://blog.sentry.io/building-for-t... • Carl Eschenbach: / carl-eschenbach-980543 • Chris Jennings: / chriskjennings • David Cramer: / dmcramer • FRC’s product market fit framework: https://pmf.firstround.com/ • Martin Casado: / martincasado • Pat Gelsinger: / patgelsinger • Raghu Raghuram: / raghuraghuram • Riverbed: https://www.riverbed.com/ • Sentry: https://sentry.io/ • Todd Bazakas: / todd-bazakas-b5a2533 • Veritas: https://www.veritas.com/ • VMware: https://www.vmware.com/ — Where to find Milin Desai: • LinkedIn: / milin-desai-464757 • Twitter/X: / virtualmilin — Where to find Brett Berson: • LinkedIn: / brett-berson-9986094 • Twitter/X: / brettberson — Where to find First Round Capital: • Website: https://firstround.com/ • First Round Review: https://review.firstround.com/ • Twitter/X: / firstround • YouTube: / @firstroundcapital • This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:03) Joining Sentry as an external CEO (06:27) The CEO/founder relationship (09:37) Lessons from VMware (13:04) What PMs did differently at VMware (18:04) Becoming the need, not the want (20:53) Scaling Sentry (23:07) Building for the “Fortune 500,000” (27:02) Open versus closed source product (30:43) The key ingredients to Sentry’s success (36:21) How Milin updated his playbook at Sentry (38:49) Focus on packaging, not pricing (40:29) “Build for the many, not the few” (41:53) Sentry’s B2D model (45:10) The second product mindset (51:03) Contrarian take on building for enterprise (52:50) Several people who influenced Milin