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

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-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/


—
Where to find Milin Desai:

LinkedIn: https://www.linkedin.com/in/milin-desai-464757/


Twitter/X: https://twitter.com/virtualmilin


—
Where to find Brett Berson:

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/


Twitter/X: https://twitter.com/brettberson


—
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


—
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