Matthew Wolf

Matthew Wolf is the Head of Underwriting AI Innovation at The Guardian Life Insurance Company of America (Guardian). In this role, he leads Guardian's Underwriting Design Lab, where he helps reimagine the life and disability insurance purchase and underwriting experience through the deployment of AI and machine learning technologies.

Previously, Matthew served as the founding Head of Product & Actuary at Dayforward, where he bridged software development and insurance product design to launch the company's innovative life product and lead the development of its proprietary technology platform. In that role, he drove digital conversion and automated customer journeys while overseeing pricing, regulatory filings, accelerated underwriting, and reinsurance strategy.

Earlier in his career, Matthew led actuarial product development and data analytics teams at Haven Life, MassMutual's digital life insurance business, and held actuarial positions at Zurich North America and AXA Equitable.

A Fellow of the Society of Actuaries with 20 years of industry experience, Matthew combines hands-on insurtech leadership with deep technical insurance expertise to drive transformation at scale.