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Reinforcing consensus-driven culture, deploying the “inverse Conway maneuver” & the unique principles behind Two Sigma’s engineering culture

with Matt Greenwood

February 6, 2024
Reinforcing consensus-driven culture, deploying the “inverse Conway maneuver” & the unique principles behind Two Sigma’s engineering culture
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Matt is Chief Innovation Officer and Head of Investment Management Engineering at Two Sigma. He joined Two Sigma in 2003 and since then has led a number of company-wide efforts in both engineering and modeling. Matt is also an Advisor at Two Sigma Ventures and works closely with the business’ portfolio companies as a board member and advisor.

Matt began his career at Bell Labs and later moved to IBM Research, where he was responsible for a number of early efforts in tablet computing and distributed computing. In 2000, Matt was lead developer and manager for Entrisphere, Inc., where he helped create a product providing access equipment for broadband service providers. Matt earned a BA and MA in Math from Oxford University, and a Master’s degree in Theoretical Physics from the Weizmann Institute of Science in Israel. He also holds a PhD in Mathematics from Columbia University, where he taught for many years.

"We came to New York in 2003, nothing was happening in New York. Silicon Alley, as they called it back then was just kaput. Then one day, I was browsing Craigslist, because that's what you did in 2003, and there was a little ad, ‘Hedge fund, looking for excellent engineers.’ So I was like, 'All right, maybe.' I said to my wife, 'This is either the sketchiest thing ever or the best decision of my life. It's one of those two things.' On Craigslist, there's no other way you can be, right? And it was probably the best decision of my life.”

<cite>- Matt Greenwood    </cite>

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  • Matt’s eng leadership journey & discovering Two Sigma on Craigslist (3:34)
  • Key moments of Two Sigma’s evolution as an org that sparked excitement (7:26)
  • Lessons learned on keeping your work exciting by focusing on “human problems” (10:25)
  • Create a culture of investing in people’s growth across longer timelines (12:22)
  • How Sigma Two intentionally structures its R&D org (15:18)
  • An unexpected way to prepare for scaling your org - intentional relationship-building strategies for your first-line managers (18:10)
  • Frameworks for deploying the inverse Conway maneuver (20:56)
  • The right people / conversations for small & large reorgs (23:30)
  • Consensus-driven culture at 1000+, approaches to create buy-in & ownership with organizational change (26:02)
  • Two Sigma’s approach to full-bodied problem solving (30:26)
  • Rapid fire questions (34:06)


  • Whalefall - A scientifically accurate thriller from Daniel Kraus about a scuba diver who’s been swallowed by an eighty-foot, sixty-ton sperm whale and has only one hour to escape before his oxygen runs out.

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

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