Life keeps happening. He built a company to handle it.
There's a startup in New York called Overalls. Its tagline reads: "$#it happens." Enterprise HR departments loved it. Former Spanx CEO Laurie Ann Goldman - who taught Jon Cooper that how you communicate matters as much as what you say - would be proud.
Cooper co-founded Overalls in August 2021, roughly the same month he exited his previous company. Not a gap year. Not a strategic pause. Just: sold one, started another. That's not impatience. That's pattern recognition. He had already spent nearly a decade inside the insurance and benefits industry and knew exactly which problems nobody was solving.
"A majority of people dread dealing with insurance issues and don't think about insurance until it's too late. We want to demystify insurance and focus attention on what matters most to people - saving time, celebrating important milestones and planning for the future."
- Jon Cooper, Co-founder & CEO, OverallsThe product is called LifeConcierge. It combines AI-augmented technology with real human specialists who handle the daily chaos that employees bring to work inside their heads - childcare coordination, passport renewals, medical billing disputes, pet emergencies, estate planning, home repairs. The kind of problems you spend three hours on hold trying to fix while pretending to be in a meeting.
Overalls measures results in hours, not features. Users unlock approximately 3.2 hours per week. Twelve percent improvement in team output within a quarter. Eighty-plus NPS - higher than what Apple typically scores with its own customers, and Apple fans wait in line overnight for phones.
In 2026, Fast Company ranked Overalls #7 in the Workplace category of its World's Most Innovative Companies list. The "Small and Mighty" recognition acknowledged what happens when a lean team of roughly 110 people achieves outsized impact. Cooper would probably say the outsized impact was always the plan.
"The job of a leader is to enable its people to perform at their highest level."
- Jon CooperBefore Overalls, there was Life.io. Cooper founded it in 2012 - a behavioral insurance customer engagement platform built on social psychology and behavioral economics. He ran it for nine years and sold it to Zinnia in 2021. Then he took what he'd learned about how people actually interact with insurance (reluctantly, late, usually after something went wrong) and applied it to the employer benefits market at scale.
The career path before Life.io tells you something about how Cooper approaches complexity. He started in strategy consulting at Oliver Wyman. Moved into corporate development and operations at WellCare. Joined TriZetto as Chief of Staff, where he played a key role during the company's $2.7 billion acquisition by Cognizant. Then he spent time at CodeRyte before deciding to build something from scratch.
He graduated from the University of Pennsylvania and holds an MBA from Wharton. He speaks English, French, and Spanish. His morning routine: espresso, cold showers, and sunlight. The man runs a company that helps employees manage stress while apparently stress-testing himself with ice water before 8am.