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.
Company: Overalls Inc
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.
How has your approach to leadership evolved to meet the changing expectations of today’s workforce, especially regarding remote and hybrid work?
Jon Cooper: In its simplest form, the job of a leader is to enable its people to perform at their highest level. With more than three quarters (77%) of employees burnt out it is clear employees need help. People are juggling complex jobs with complex lives, from caregivers to managing health conditions, or working multiple jobs – the stress of everyday life is affecting people’s ability to perform at the highest level.
At Overalls, we responded to this need by introducing Overalls LifeConcierge™, providing employees with support for life’s daily frustrations and complex tasks, ultimately reducing stress and improving productivity. By taking a proactive approach to help employees manage both work and personal responsibilities, we clear the roadblocks that stand in the way of employee productivity while creating a more supportive work environment where people feel valued. This flexible, understanding approach aligns with the needs of today’s workforce, allowing us to stay responsive to the changing expectations around remote and hybrid work.
What specific strategies have you implemented to foster Diversity, Equity, and Inclusion (DEI) within your organization?
Jon Cooper: As the workforce has become more diverse, so have the myriad of life experiences, situations, and challenges employees face. Traditional employee benefits were for a different era, when the workforce was more homogenous and their needs more predictable, and by default are exclusionary. As workforce diversity has increased, this has created a situation where traditional point-solutions benefits (e.g., caregiving benefit or medical navigation) only address the needs of a small fraction of the workforce, while excluding the needs of other employees. As a result, in an attempt to address the needs of the entire workforce, companies have been in a vicious cycle of introducing an ever growing list of point-solutions (e.g., fertility, financial wellness, commuter benefits, work from home benefits, student loan forgiveness, etc) leading to a patchwork of point-solutions that are expensive, difficult to manage, and still exclude many of the needs employees face.
In contrast, Overalls by default is designed to be inclusive. The LifeCconcierge™ solution is akin to having a team of personal assistants and experts in domains such as healthcare, law, personal finances, travel, and more, working to solve whatever problem arises for your employees. This combination of breadth and depth allows us to equitably support the diverse and complex needs facing a truly diverse workforce.
How do you keep your team engaged and motivated in a workplace culture that increasingly values flexibility and work-life balance?
Jon Cooper: We believe that people do their best work when they have the flexibility and support to be productive and feel valued, in a working environment where growth and development are encouraged. For this reason, all of our team members have access to Overalls, as well as the flexibility to work from home or from one of our offices, and to enjoy our flexible vacation policy. This works for Overalls in part because we have a very stringent hiring process, where we carefully recruit for self-driven candidates with a growth mindset, who are motivated by our company mission.
Our simple but profound company mission is to simplify life for our users. Many companies say this, but at Overalls, our mission is deeply woven into the DNA of our company culture. Beyond highlighting our mission statement in our employee handbook and on the walls of our office, we celebrate our mission daily with our entire workforce by constantly reminding us of the challenges employees face and celebrating the successes our LifeConcierges achieve by resolving these problems. At one point or another, every employee will shadow a LifeConcierge, and whether you’re in our marketing, accounting, or operations department, you’re responsible for supporting our LifeConcierges and our users. For example, just last week, we had a user traveling to Paris for work where he needed help resolving an issue between his bank and the local Parisian bank. Since I speak French and have a lot of experience dealing with the French services industry. I teamed up with our LifeConcierge to sort out this issue for our end users. Keeping everyone connected to our users and the company mission is highly motivating.
What do you see as the biggest challenges in preparing for the future workforce, and how are you addressing them?
Jon Cooper: One of the biggest challenges we see in preparing for the future workforce is the need for rapid reskilling, especially as AI and other technologies continue to reshape how work is done. As this accelerates, it will be essential for employees to adapt to new tools and processes. At Overalls, we brought on AI experts to train our team and are simultaneously equipping our existing staff with the skills to incorporate these tools into their daily work. This approach not only ensures our team is prepared for the future but also helps us remain competitive in a fast-evolving industry. By investing in the growth of our workforce and focusing on adaptability, we’re building a workforce that’s ready to meet the challenges of tomorrow.
How has the shift toward digital and remote collaboration affected your company culture, and what adjustments have you made to maintain a strong, cohesive team?
Jon Cooper: We value autonomy and a growth mindset in all of the people we bring to Overalls. The shift toward digital and remote collaboration has underscored the importance of fostering a supportive culture that bridges the gap between work and personal life. At Overalls, we recognize that life’s challenges don’t stop when employees work remotely, so we implemented Overalls LifeConcierge™ to support our team with personal tasks and reduce stress. This initiative allows employees to stay focused and productive, no matter where they are working.
To maintain cohesion, we also emphasize continuous feedback and communication, ensuring that every team member feels connected and supported, even in a remote setting. By integrating flexible, people-centric solutions and prioritizing well-being, we’ve been able to create an inclusive culture that supports each employee, keeping our team strong, engaged, and unified with the flexibility to work wherever suits them best.
