Insight Partner's Nick Sinai named Eagle Award winner at gala

Nick Sinai can trace the launch of his career as a leader in government technology delivery to the 2008 financial crisis.

Sinai and his new wife had taken a red-eye flight to Italy for their honeymoon that September. Upon landing, Sinai learned about the collapse of Lehman Brothers from a newspaper headline. He’d been working at Lehman’s venture arm for about nine months and upon his return, he had to look elsewhere for work.

He was hired at the Federal Communications Commission to work on the National Broadband plan, an ambitious effort to incentivize the development of high-speed internet across the U.S. while transitioning to faster mobile technologies.

“That was my first exposure to policymaking as a grown-up, and it was tremendously exciting,” Sinai said, now a senior advisor with the investment firm Insight Partners. Their portfolio includes companies such as Exiger, PluralSight and HawkEye 360.

That experience connected him with a new generation of government techies who were starting to focus on then-novel concepts like agile development and user-centered design. He joined the White House Office of Science and Technology Policy under Chief Technology Officer Aneesh Chopra as an advisor and served as deputy CTO under Chopra’s successors Todd Park and Megan Smith.

Before long, the Healthcare.gov debacle saw a lot of the staff of OSTP detailed to the rescue effort. Sinai stayed at OSTP, but some of the programs he sponsored supplied personnel needed to get Healthcare.gov on track — and helped supply a proof of concept for in-house digital innovation groups like 18F and the U.S. Digital Service.

The experience and knowledge gained at OSTP also provided fodder for the 2022 book Hack Your Bureaucracy, co-written by Sinai and former Veterans Affairs CTO Marina Nitze.

The tactics in the book are “fundamentally about understanding the organization and understanding people and processes and why things are the way they are before you go try and disrupt them and change them,” Sinai said. “Some people think ‘hack’ is a pejorative term, but we really see it as a way to improve government, and it starts with understanding the problem space and understanding the end users.”

Today Sinai works as an venture capitalist, but that description doesn’t cover his impact on the federal technology community. 

“He has a deep understanding of the policymaking process …  he has the judgment of an investor focused on early-stage companies capable of identifying sparks that might scale to deliver meaningful impact, and he is a talented operator who can see the kindling of promising ideas all the way through implementation,” Chopra told Nextgov/FCW. 

A former colleague, Erie Meyer, now chief technologist at the Consumer Finance Protection Bureau, said that Sinai is “one of the first lifelines I call when I have a hard problem.”

“Nick is smart, tough and kind,” Meyer said. “I’ve learned a lot from him, but my favorite thing is the discipline of how to learn a lot from people. He’s constantly cultivating community, helping people stretch and asking sharp questions.”