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Gill Shklarski is a General Partner at Operator Partners and the Chief Technology Officer at Thirty Madison, based in New York, New York. He previously served as the Chief Technology Officer at Flatiron Health, where he scaled the engineering team from two to 350 employees leading up to the company's $1.9 billion acquisition by Roche in 2018. Before his tenure at Flatiron Health, Shklarski managed research and development for the Israeli Ministry of Defense and earned a doctorate in scientific computing from Tel Aviv University. Since joining Operator Partners in 2020, he has directed early-stage venture capital investments across the infrastructure, developer tooling, corporate IT, cybersecurity, and employee productivity sectors. His current professional focus centers on scaling complex engineering organizations and advancing digital health initiatives through both executive leadership and strategic venture capital deployments.
Gill Shklarski stands as a distinguished General Partner and co-founder at Operator Partners, a venture capital firm uniquely positioned by its operator-led investment philosophy. With a career deeply rooted in building and scaling transformative technology companies, Shklarski brings an invaluable blend of firsthand operational experience and strategic investment acumen to the early-stage ecosystem. His role at Operator Partners involves leading investments, providing mentorship, and offering strategic guidance to founders, embodying the firm's commitment to empowering the next generation of technology leaders.
At Operator Partners, Gill Shklarski's investment focus areas are sharply defined and reflect his expertise in foundational technology. He primarily targets early-stage companies innovating within B2B SaaS, fintech, developer tools, and core infrastructure. He seeks out ventures with strong technical foundations, clear market opportunities, and ambitious founders who are building essential tools and platforms that enable other businesses to thrive. His approach is hands-on, extending beyond capital provision to include deep engagement with portfolio companies on product strategy, engineering scaling, and market penetration.
Shklarski's career background is a testament to his profound understanding of technology development and organizational growth. Prior to co-founding Operator Partners, he served as the Chief Technology Officer (CTO) at Stripe during its critical early growth phase (2010-2014). In this pivotal role, he was instrumental in scaling Stripe's engineering organization and developing its robust, developer-centric payment infrastructure that revolutionized online commerce. Following his impactful tenure at Stripe, he continued his leadership journey as CTO at Cadre, a real estate technology platform, further honing his skills in building complex systems and leading high-performing technical teams. This extensive operational history provides him with a unique lens through which to evaluate technical talent, product roadmaps, and market fit, making him a highly sought-after partner for founders.
His investment philosophy is deeply informed by these experiences. Gill understands the intricate challenges and immense opportunities founders face, allowing him to offer practical, actionable advice that resonates deeply. While specific portfolio companies are often confidential in early-stage venture capital, his involvement signals a strong belief in the technical merit and market potential of the ventures he backs. Shklarski's commitment to the Operator Partners portfolio companies extends beyond financial backing; he aims to be a true partner in their journey from inception to significant market impact, leveraging his operator insights to accelerate their success.
Gill Shklarski is a General Partner and co-founder of Operator Partners, an early-stage venture capital firm. He is widely recognized for his extensive background as a technology executive, including serving as CTO at Stripe and Cadre, which informs his operator-centric investment approach.
Gill Shklarski primarily invests in early-stage technology companies within sectors such as B2B SaaS, fintech, developer tools, and infrastructure. His investment thesis often focuses on founders building foundational technologies for other businesses.
Gill Shklarski works as a General Partner at Operator Partners, the venture capital firm he co-founded, which focuses on early-stage technology investments.
