our team

Behind the Seams

Builders from Google, Life.io, Liberty Mutual, and Redesign Health—now channeling that energy into Overalls, where responsible Gen‑AI meets real-world relief. We're turning cutting-edge tech into everyday wins: helping our users navigate chaos, reclaim time, and breathe easier.

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The Dreamers

Who We Are.

Jon Cooper

Co-Founder and CEO

Serial insurtech entrepreneur; founded & scaled Life.io (acquired 2021); ex‑Chief of Staff TriZetto (sale $2.7B); strategy roles at Oliver Wyman, CodeRyte & Wellcare; Wharton MBA.

David Pass

Co-Founder and Head of Revenue

Former Vice President in Jefferies’ Healthcare Investment-Banking Group, where he advised on $25 B+ in M&A and financing deals. Incubated Overalls inside Redesign Health before taking the reins on GTM and partnerships. B.A. Economics, Vanderbilt University.

Alison Stewart

Co-Founder and COO

Insurance veteran with 15 years in P&C and Group Benefits; led ops strategy at Liberty Mutual and Lincoln Financial Group; innovated across brokerage and carrier operations.

Mike Calhoun

VP of Engineering

Ex‑CTO Life.io; senior engineering leader at Stitch Fix & Invoca; 15+ years scaling SaaS & data platforms; B.S. Computer Science, St. John’s University.

Board & Advisors

Laurie Ann Goldman

Former CEO of Avon and Spanx & Tupperware; brand‑building powerhouse.

John Geyer

Ex‑MetLife Chief Innovation Officer; EY Executive‑in‑Residence.

Missy Krasner

Founding team Google Health; Venture Chair, Redesign Health.

Pina Albo

CEO Hamilton Insurance Group; 25‑year Munich Re leader.

Advisors

Ashley Alexander

CPO, Front

Kelly Battelle

CPO, GumGum

Jim Galli

Consultant

Menaka Chang

Fractional People People Leader

Vinay Gidwaney

CProdO, OneDigitl

Emily Couey

Lead Consultant, Build Hr

Cindy Gordon

CHRO and Consultant

Kara grenier

CPO and Advisor

Matt Hoffman

Partner and Talent, M13

Mindy Honcoop

HR Advisor, Agile in HR

Bob Lehto

VP People, Discreet Lab

Stephen Liptrap

Former CEO, LifeWorks

Lori McAdams

Intermin CPO, SeatGeek

Stacey Nordwall

Head of EZ, Pyn

Anthony Onesto

CPO, Suzy

Aviad Pinkovezky

President, First Connect

Byron Revels

VP Partners, Origon

Anthony Rotoli

Co-Founder, Speak_

Heather Robertt

HR Consultant

Yann Sauvignon

Head of Sales, Lumos

Caitlin Schlakman

VP People, Motive

Dawn Sharifan

CPO, Positively Selfish

Karen Shine

Wellbeing Professional

Jessica Yuen

HR Advisor and Founder

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