Lessons from Sentry on scaling DevTools and finding product market fit (again) | Milin Desai (Sentry, VMware, Riverbed)

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.

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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

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Referenced:

• Building for the Fortune 500,000: https://blog.sentry.io/building-for-the-fortune-500-000/
• Carl Eschenbach: https://www.linkedin.com/in/carl-eschenbach-980543/
• Chris Jennings: https://www.linkedin.com/in/chriskjennings/
• David Cramer: https://www.linkedin.com/in/dmcramer/
• FRC’s product market fit framework: https://pmf.firstround.com/
• Martin Casado: https://www.linkedin.com/in/martincasado/
• Pat Gelsinger: https://www.linkedin.com/in/patgelsinger/
• Raghu Raghuram: https://www.linkedin.com/in/raghuraghuram/
• Riverbed: https://www.riverbed.com/
• Sentry: https://sentry.io/
• Todd Bazakas: https://www.linkedin.com/in/todd-bazakas-b5a2533/
• Veritas: https://www.veritas.com/
• VMware: https://www.vmware.com/

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Where to find Milin Desai:

• LinkedIn: https://www.linkedin.com/in/milin-desai-464757/
• Twitter/X: https://twitter.com/virtualmilin

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Where to find Brett Berson:

• LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
• Twitter/X: https://twitter.com/brettberson

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Where to find First Round Capital:

• Website: https://firstround.com/
• First Round Review: https://review.firstround.com/
• Twitter/X: https://twitter.com/firstround
• YouTube: https://www.youtube.com/@FirstRoundCapital
• This podcast on all platforms: https://review.firstround.com/podcast

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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