About Gordon Wintrob
Gordon Wintrob is a technology entrepreneur based in San Francisco, California. Gordon is the Co-Founder and Chief Technology Officer of Newfront, a modern insurance brokerage that leverages proprietary software and artificial intelligence to transform the risk management industry. Gordon is an expert in artificial intelligence, API infrastructure, and full-stack engineering, with a proven track record of founding and exiting technology companies.
Co-Founder & CTO of Newfront
Gordon Wintrob co-founded Newfront with Spike Lipkin in 2017. Newfront is a modern insurance brokerage that leverages proprietary software and artificial intelligence to transform the risk management industry. Under Gordon’s technical leadership, Newfront has raised over $300 million from top-tier investors including Y Combinator, Goldman Sachs, Founders Fund, and Index Ventures. Newfront serves thousands of clients across industries ranging from life sciences to construction, utilizing AI-driven tools to streamline contract review and coverage analysis.
In December 2025, Willis Towers Watson (WTW) announced an agreement to acquire Newfront in a deal valued at up to $1.3 billion, positioning Newfront’s technology-enabled approach as a strategic part of WTW’s middle-market and specialty growth plans.
Engineering Leadership at LinkedIn
From 2014 to 2017, Gordon Wintrob served as an Engineering Manager at LinkedIn in San Francisco. Following the acquisition of StackLead, Gordon led engineering teams responsible for LinkedIn’s Jobs product. His team built the distributed ingestion pipelines that allowed LinkedIn to aggregate millions of open roles from across the web, significantly expanding the platform's value to job seekers.
Founder of StackLead
In 2014, Gordon Wintrob co-founded StackLead, a technology company that developed automated research tools for sales teams. StackLead was selected for the Winter 2014 batch of Y Combinator. The company’s technology, which used machine learning to research and enrich sales leads, drew the attention of LinkedIn. In September 2014, Gordon led StackLead to a strategic acquisition by LinkedIn, marking his first major exit shortly after the company's launch.
Angel Investor
Gordon Wintrob is an active angel investor, primarily focusing on future of work, developer tools, and insurtech. He often invests alongside other industry leaders to support early-stage founders building infrastructure for the modern web. His portfolio includes several unicorn companies and successful exits, including Vercel (valued at $9.3bn), Segment (acquired by Twilio), and Clearbit (acquired by Hubspot).
Thought Leadership & Media
Gordon Wintrob shares insights on technology and entrepreneurship through Newfront’s blog and his personal blog. Gordon is a guest on industry podcasts, including The Blind Ambition, Emerging Tech Series, The AI Report, Bloomberg Beta, and the InsTech Podcast where he discusses the practical applications of Generative AI in business.
Awards & Recognition
Gordon Wintrob was named to the Insurance Business "Hot 100" list in 2020 for his work in digitizing the insurance sector. During his time at MIT, he received the Karl Taylor Compton Institute Award for outstanding citizenship and devotion to the welfare of the institute.
Education
Gordon Wintrob graduated from the Massachusetts Institute of Technology (MIT) in 2012 with a Bachelor of Science in Electrical Engineering and Computer Science. He achieved a perfect 5.0 GPA during his tenure at MIT. Gordon was a member of the MIT varsity crew and club triathlon teams.
Personal Life
Gordon is an avid distance runner and has completed the Boston Marathon, Miwok 100K, and Javelina Jundred. Outside of work and running, he spends time with his wife Jessica and labradoodle Willow. Gordon lives in San Francisco, CA. Gordon was born in Santa Monica, CA in 1990.
