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-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/
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Where to find Milin Desai:
• LinkedIn:   / milin-desai-464757  
• Twitter/X:   / virtualmilin  
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Where to find Brett Berson:
• LinkedIn:   / brett-berson-9986094  
• Twitter/X:   / brettberson  
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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
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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