Jon Cooper of Overalls Inc.: Evolving Leadership Strategies for a Flexible Workplace

Jon was founder and CEO of Life.io, a pioneer insurtech that successfully recast digital customer engagement for life insurance. Jon’s insurance expertise was developed during strategic roles from Chief of Staff to Strategy and Operations at TriZetto, Oliver Wyman, CodeRyte and Wellcare.

Jon dreams of teaching his family French and moving for a year to the south of France.

We are thrilled to have you join us today, welcome to ValiantCEO Magazine’s exclusive interview! Let’s start off with a little introduction. Tell our readers a bit about yourself and your company

Jon Cooper: Thank you for the opportunity to share our story with ValiantCEO! I’m Jon Cooper, Founder and CEO of Overalls Inc., where we focus on simplifying life for employees so they can stay productive and reduce stress. Some might call me a serial entrepreneur with experience in employee benefits, insurtech, and healthtech, but what I’m really passionate about is tackling life’s everyday complexities to improve well-being. After experiencing the toll of life’s challenges firsthand, Overalls LifeConcierge™ was born as a unique support solution designed to help employees navigate life’s issues and frustrations.

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8 Trends Will Redefine The Workplace And Your Career In 2025

As we move into 2025, the workplace landscape is evolving rapidly, and the challenges that employers and employees face are more dynamic than ever. Business leaders on the front lines are making predictions about the future of the workplace. Among those predictions are the death of return-to-work policies and that AI will replace full-time careers for some employees. Now, predictions are coming in about what trends will redefine the workplace in the coming year.

Eight Trends Will Redefine The Workplace In 2025

I spoke with Jon Cooper, CEO and co-founder of Overalls, a modern employee benefits offering. He looked in his crystal ball and told me by email that eight key trends will redefine the workplace and your career in the coming year.

1. A competitive hiring landscape driven by economic growth. “As the economy strengthens, businesses will face heightened competition for top talent,” Cooper says. “This will push companies to re-imagine and expand their benefits offerings, emphasizing flexibility and inclusivity to attract and retain employees in a fiercely competitive market.”

2. Inclusive benefits for a diverse workforce. Cooper believes the era of exclusionary, one-size-fits-all benefits is fading. “Companies will prioritize simpler, more inclusive solutions tailored to the needs of diverse teams, ensuring employees at all levels feel supported and valued,” he claims.

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Ten to Watch in 2025: Stephen Chen, Boldin

Stephen Chen wants to get financial planning into the hands of 100 million people—and working with advisors will help him get to that goal.  

He has spent the last decade growing his consumer-focused financial planning startup Boldin—previously called ‘NewRetirement.’ Almost 400,000 consumers have accessed the platform, which provides tools for analyzing their financial wellness or building personal financial plans.

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Boldin Financial Planner Review: Financial Freedom Made Easier

I recently had dinner with Steve Chen, founder of Boldin, in San Francisco, and I’m excited to deepen my partnership with his company. Since first writing about Boldin (formerly NewRetirement) in 2020, I’ve seen how much the platform has evolved and expanded its offerings.

The world needs a financial planning tool that takes a holistic approach to wealth management. As someone with real estate investments, alternative investments, private investments, and two young children who may attend college one day, I’ve found Boldin excellent for managing a complicated net worth beyond just stocks and bonds.

Recently, I was also grappling with questions about what qualifies as income versus capital gains when withdrawing from a 401(k), IRA, Roth IRA, and taxable brokerage accounts in retirement. At 47, I’m 13 years away from traditional retirement, and I’m focused on creating a tax-efficient withdrawal strategy to maximize my funds. Boldin offers the tools and guidance to address these complex, yet essential, questions.

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Axiom Cloud Introduces Enhanced Compliance Reporting to Help Grocery Retailers and Cold Storage Operators Meet Critical EPA and CARB Requirements

AI-powered solution now streamlines required reporting for Automatic Leak Detection (ALD) ahead of January 1, 2026 EPA deadline

SAN JOSE, Calif., Dec. 4, 2024 /PRNewswire/ -- Axiom Cloud, a leader in AI-powered refrigeration management solutions, today announced the launch of Enhanced Compliance Reporting within its AI-powered Early Leak Detection module. This new feature helps grocery retailers and cold storage facilities become "audit-ready" before the EPA begins enforcement of the AIM Act on January 1, 2026. By generating reports for ALD systems and leak events that are required for recordkeeping and self-reporting on an ongoing basis, Axiom helps its customers achieve compliance with EPA regulations and existing CARB requirements.

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