The Quietest $3B Tech Company You’ve Never Heard Of

The AI Report Live

This week on The AI Report, Liam Lawson sits down with Gordon Wintrob, co-founder and CTO of Newfront, to talk about bringing AI into one of the slowest-moving industries: insurance.

Gordon shares how Newfront is redesigning the broker experience with automation and AI—from parsing 200-page policies in seconds to helping HR teams save weeks of work. They discuss building AI tools that clients actually trust, how to manage risk in regulated industries, and why embedding AI into company culture matters as much as the code.

Also in this episode:

• Why insurance is one of the last big frontiers for tech

• What makes a good AI use case in complex workflows

• The story behind Benji, Newfront’s internal AI assistant

• How to foster internal adoption from hiring to hackathons

• What regulation and SOC 2 mean for AI innovation

This is a real look at what happens when AI goes beyond chatbots and into core business infrastructure.

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Chapters:

(00:00) Reimagining the Insurance Stack

(01:06) Why Insurance Feels So Behind

(02:41) How Brokers Work and Where AI Fits

(05:08) Founding Newfront With Future Tech in Mind

(06:59) Automating Contract Review at Scale

(08:49) Working With Startups and Industry Giants

(10:19) What It’s Like Serving Diverse Client Profiles

(12:17) Making Room for Value-Add Conversations

(13:28) Key AI Tools: Benji, Gap Analysis, and More

(15:29) Why Products Succeed or Fail in Legacy Fields

(16:39) Creating a Culture of Technical Curiosity

(18:25) From Engineering to Recruiting: AI in the Org

(19:30) Equity, Values, and Ownership at Scale

(21:50) What Keeps Traditional Brokerages Behind

(23:43) AI as a Signal of Operator Leverage

(25:22) Who Newfront Builds For

(25:56) Staying Compliant While Moving Fast

(28:39) Managing Data Risk in a Privacy-Critical Industry

(29:01) Vendor Security and SOC 2 in AI Development

(30:25) Expanding AI Beyond the Frontend

(31:58) CTO Strategy and Time Allocation

(32:54) Staying Up-to-Date in a Fast-Shifting Landscape

(34:42) Building With Purpose in a Legacy System

(36:11) Connect With Gordon