Gil Shklarski

Background

Gil Shklarski is a General Partner at Operator Partners, a self-funded venture firm he co-founded in 2020 with Nat Turner, Zach Weinberg, and Amit Avner ¹². He is based in New York ³.

Shklarski spent 10 years in the Israeli Defense Forces (IDF), where he developed high-performance, mission-critical systems as a researcher, consultant, and R&D group manager in elite technology units within Israel’s Ministry of Defense ⁴⁵. He holds a PhD in computer science in the field of scientific computing from Tel Aviv University ³⁵.

After completing his PhD, Shklarski worked at Microsoft, where he built large-scale data processing systems including infrastructure for Microsoft Maps ⁴⁵. He then joined Facebook, where he worked on data pipelines for fraud detection and identifying bad actors on the platform ⁴⁵.

In September 2012, Shklarski joined Flatiron Health as the second engineer ⁴⁵. He served as CTO for nine years, growing the technology organization from two people to over 350 professionals spanning engineering, DevOps, IT, security, product design, and data science ³⁵. Flatiron Health was acquired by Roche for $1.9 billion in 2018, and Shklarski continued as CTO through and after the acquisition ³⁶.

In September 2023, Shklarski joined Thirty Madison as CTO, leading the technology organization delivering virtual-first specialty healthcare ⁷. He is also a Scientific Co-Founder and Board Observer at NeuraLight, an AI-driven neurology startup he invested in early and formally joined in November 2021 ⁶⁸.

Stated Thesis

Operator Partners publicly describes its approach as “operators funding operators,” investing exclusively with the partners’ own capital and no outside LPs ¹². The fund writes $250K-$1M checks at pre-seed, seed, and Series A stages, does not lead rounds or take board seats, and offers on-demand operational support ²⁹.

Shklarski’s personal focus areas span infrastructure, developer tooling, corporate IT, cybersecurity, employee productivity, and digital health ³. His background positions him as the fund’s technical and healthcare domain expert. VCSheet lists his sector focus as devtools, enterprise, cybersecurity, future of work, and health ¹⁰.

Inferred Thesis

Based on 11 verified investments in the portfolio table below, the following patterns emerge. Note: Shklarski’s total investment count across angel and Operator Partners activity is likely higher, so these percentages should be treated as directional only.

Sector breakdown (11 verified investments): - Healthtech / Digital Health: 4 of 11 (36%) — NeuraLight, Nym Health, Nirvana Health, Assured Allies - Cybersecurity / Infrastructure Security: 3 of 11 (27%) — Canonic Security, Otterize, Immuta - Enterprise / Compliance: 2 of 11 (18%) — RightBound, Thoropass - Fintech: 1 of 11 (9%) — Cardless - AI / Legal Tech: 1 of 11 (9%) — Crosby

Stage distribution (11 verified investments): - Seed: 9 of 11 (82%) — Cardless, Nym Health, NeuraLight, Nirvana Health, Immuta, Thoropass, Canonic Security, Otterize, Crosby - Series A: 2 of 11 (18%) — RightBound, Assured Allies

Geographic patterns: Portfolio includes a significant proportion of Israeli-founded companies (NeuraLight, Nym Health, Canonic Security, Otterize, RightBound, Assured Allies — 6 of 11, 55%), reflecting Shklarski’s Israeli background and the fund’s Tel Aviv connection through partner Amit Avner ¹.

Co-investor patterns: Shklarski frequently co-invests with Operator Partners co-founders Nat Turner and Zach Weinberg, as confirmed in the RightBound Series A ¹¹. The fund co-invests alongside established lead investors including Sequoia Capital, First Round Capital, Index Ventures, and Innovation Endeavors ^11121315.

Founder profile patterns: Strong tilt toward technical founders tackling complex data and infrastructure problems, particularly in healthcare and security. The healthcare concentration (36%) is notably higher than Operator Partners’ overall portfolio mix, consistent with Shklarski’s Flatiron Health background.

Notable gap: Despite the stated focus on “employee productivity” and “future of work,” no verified investments in that category were found in this sample.

Portfolio

This table represents Shklarski’s individually attributed investments, combining angel activity prior to Operator Partners and investments made through the fund. Many entries use approximate years based on company founding or funding announcement dates. Operator Partners as a firm has invested in 144+ companies ¹⁶, but individual partner attribution is limited in public data.

Two additional companies (Canopy Care and an unnamed Israeli startup) were referenced in aggregator profiles but could not be verified with sufficient detail for inclusion.

In Their Own Words

“Engineering would never be the bottleneck for creativity in how we build a business.” — Gil Shklarski, Enigma interview, 2018 ⁴

“Never be afraid to hire people who are smarter than you. Rather, do the opposite.” — Gil Shklarski, Enigma interview, 2018 ⁴

“Cancer kills more people than Al-Qaeda. With this mission, you feel less helpless.” — Gil Shklarski, Enigma interview, 2018 ⁴

“Your goal is basically…to be opportunistically lazy. You want to automate yourself out.” — Gil Shklarski, Enigma interview, 2018 ⁴

“As you scale, one team turns into many, and each one needs to run on its own and feel good about making decisions locally without parental supervision.” — Gil Shklarski, First Round Review ¹⁷

“When I make decisions this way, I always say, ‘Okay, this is where we ended up. Here is your 24 hour freakout window, during which we can revisit the decision.’” — Gil Shklarski, First Round Review ¹⁷

“Having been an early investor in NeuraLight from the start, I’ve been impressed with the quality of people the company has brought on and the velocity in tech, clinical, and commercial discovery they’ve had in the last year. I decided to join as an integral part of the team because I truly believe the team and technology have the potential to transform the lives of people with neurological disorders.” — Gil Shklarski, NeuraLight press release, November 2021 ⁸

“I’m excited about the impact Thirty Madison has already delivered for patients…massive opportunity ahead to scale specialty-level healthcare.” — Gil Shklarski, Thirty Madison press release, September 2023 ⁷

What Founders Say

“Adding Gil to our team is one of those rare inflection points that will change the trajectory of our company for years to come. Gil is not only one of the most brilliant operators we’ve worked with, but one of the most dedicated and thoughtful ones, and having Gil’s expertise in the digital health space will be invaluable as we drive forward into 2022.” — Dr. Micha Breakstone, CEO and Co-Founder of NeuraLight, November 2021 ⁸

“Gil joins Thirty Madison with deep understanding of engineering management and high-performing teams tackling complex technology challenges.” — Steve Gutentag, CEO of Thirty Madison, September 2023 ⁷

No additional independently sourced founder testimonials from portfolio company founders were found. The quotes above are from NeuraLight (where Shklarski is Scientific Co-Founder, not purely an investor) and Thirty Madison (where he was hired as CTO, not an investor relationship).

Sources