JC

Jon Cooper

Co-Founder & CEO at Overalls
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Jon Cooper is a serial entrepreneur and change agent specializing in employee benefits,insurtech, and healthtech. As the Founder and CEO of Overalls, he's redefining employee well-being with Overalls LifeConcierge™, a solution that simplifies life's complexities. His career milestones include founding Life.io, a disruptive platform in the insurance sector acquired in 2021, and strategic roles at TriZetto, Wellcare and Oliver Wyman. An MBA from The Wharton School and a BA from the University of Pennsylvania round out his credentials.

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  • Overalls CEO Advocates for Proactive Stress Prevention in the Workplace
    Jon emphasizes that workplace stress persists due to life stressors impacting work hours. Overalls' data shows employees lose 2.3 hours per stress incident. He advocates for shifting from stress management to prevention, using tools like Overalls’ LifeConcierge™. HR should lead with leadership support, treating stress as a business issue. Third-party experts can provide tactical help, addressing life disruptions directly.
  • Empathy and Creativity: The Future of Human-Centered AI
    Jon emphasizes empathy in AI design, especially in customer-facing tools, raising ethical questions about AI's role in personal relationships. He highlights AI's potential in creativity, from art to content creation, and stresses collaboration over replacement. Jon believes in "keeping humans at the center as AI evolves," ensuring technology serves people, not just business goals.
  • 2025 CEO Outlook: Navigating Talent Wars and AI Integration
    Jon highlights the competitive hiring landscape and AI's evolving role as key 2025 challenges. He emphasizes, "Companies must offer inclusive benefits and view AI as an enabler, not a threat." Flexibility in work arrangements and innovative health benefits will be crucial. Leaders should prepare for legislative shifts and potential crises to ensure organizational resilience and growth.
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