Investing In Your Employees: Jon Cooper Of Overalls On The Benefits of Offering Continuous Professional Development (CPD) Initiatives For Employees
An Interview With Chad Silverstein
Loyalty — Employees are more likely to stay with a company when they feel like they’re developing new skills and the company is invested in their growth.
Investing in team development has become increasingly crucial for forward-thinking companies, who understand that their greatest assets are their people. From implementing innovative training programs and wellness initiatives to cultivating a supportive work environment, these strategic investments play a vital role in enhancing employee satisfaction and retention. As the business landscape evolves, mastering effective methods to support and retain employees is pivotal for achieving long-term success. I had the pleasure of interviewing Jon Cooper.
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 to reduce stress and improve productivity in the workplace. 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. When not working, Jon enjoys family time, skiing, and is trilingual.
Thank you for joining us. To start, could you share a little about yourself, and how you got started?
I love creating new things and building companies. As a result, I’ve really found my sweet spot on solving problems at the intersection of employee benefits, insurtech, and healthtech. As with many great company concepts, the idea for Overalls came from a personal experience. After a frustrating week dealing with a flood in my basement, I was reminded of the massive but largely hidden toll life’s day-to-day complexities take on people. This was more evident in the aftermath of the COVID19 pandemic, where the line between home and office became increasingly blurred. With 3 out of 4 employees struggling financially, 55% of employees managing a chronic condition, 1/3rd caring for young children at home, 18% acting as a caregiver for a parent our spouse, and 12% working multiple jobs, and major weather events and natural disasters occurring on average more than once a week, it’s no surprise that employees are incredibly stressed out and stretched thin. It became clear to me that this gap in support needed to be addressed.
What was your biggest challenge in those early days?
Starting Overalls meant breaking into a space that didn’t fully exist yet. Our biggest challenge was helping employers see this new category of LIFE (Life’s Issues, Frustrations, and Events) benefits as essential rather than just a “nice-to-have”. We like to say, “it may not be your fault, but it is your problem.” and we had to show the market how supporting employees in their personal lives directly not only improves morale but also was a major driver of productivity. It took time to get buy-in from decision-makers.
Was there anything specific that inspired you to prioritize CPD initiatives in your company?
We have been lucky enough to see great demand and growth for our solution, requiring us to scale rapidly. CPD has been instrumental in allowing us to recruit and train the talent we need to support our clients and their employees across the myriad of areas where Overalls helps employees. It is this great win-win. It allows us to deliver better quality product, while also improving the job experience for our team, and ensuring we not only attract great talent, but continue to invest in their development.
Can you explain why this is important for the success of a business?
First and foremost, CPD should be just as much an investment in upleveling the business and its performance as it is about investing in your people. If the business is not benefiting from CPD, that is a signal that either the quality or the focus of the CPD is inadequate. Beyond that, investing in employees’ continuous development is crucial because when people feel valued and supported, it shows in the quality of their work. At Overalls, we prioritize personal well-being and development as part of our core mission, and that philosophy extends into how we support our team.
Can you please share with us, and briefly explain the first major initiative you started that directly benefited your employees?
One of our first initiatives was the implementation of Overalls LifeConcierge™ for our own team. Anyone who manages a team sees just how much stress and time life’s curveballs causes their people. We wanted our employees to experience the benefits firsthand, whether it was through managing day-to-day hassles or tackling complex personal tasks that would otherwise detract from their productivity. Our team loves the support, and it has allowed us to improve our productivity, while making sure we’re building a product that our team loves.
Do you have an example of a situation where you didn’t get the result you were looking for, and tell us what happened as a result?
One of my favorite quotes is, “the obstacle is the way,” coined by Marcus Aurelius nearly 2000 years ago. Today, we might call it “failing fast” — trying, learning, and iterating until reaching the desired outcome. For any truly innovative company, this process is essential.
As a startup pioneering a new category of benefits, there was no playbook to follow. We had to test and refine almost every aspect of our solution. For example, as Overalls grew, our early team could no longer meet the increasing demands. To scale, we ran a series of rapid experiments, testing various strategies. Ultimately, this led to our unique model: partnering with former executives and professionals — like attorneys, CPAs, and nurse practitioners — who are now stay-at-home parents. This approach allows us to deliver deep expertise, scale quickly, and maintain a flexible workforce. This spirit of experimentation is central to true innovation.
What has been the most impactful CPD initiative you’ve seen other companies offer, and how did it inspire or influence your own approach?
While it is evident that personal challenges affect work performance and productivity, traditionally, many companies prioritize benefits and CPD focused on work-specific tasks. Some of our early clients recognized that if they wanted to achieve different results, they would need to think differently, and adopted Overalls to help their employees outside of work with life stressors. This required strong leaders to have conviction to lead their organization to try something new.
What challenges might companies face when implementing these initiatives, and how can they overcome them?
The biggest challenge is balancing breadth with depth. Many CPD initiatives fail because they’re either too narrow, and not applicable to enough employees to truly matter, or too general to be effective. At Overalls, we’ve made it a priority to develop our concierge model by combining experts and generalists to be truly inclusive and valuable to all employees, while giving employees support that feels tailored to their lives, which can be a game-changer.
Could you please list the “Top Five Benefits of Offering Continuous Professional Development (CPD) Initiatives For Employees”? Can you explain what you mean?
- Increased Productivity — When employees are continuously learning, they bring fresh skills and ideas, directly impacting their output and efficiency.
- Loyalty — Employees are more likely to stay with a company when they feel like they’re developing new skills and the company is invested in their growth.
- Enhanced Job Satisfaction — Learning opportunities contribute to a sense of purpose and satisfaction in the workplace.
- Improved Adaptability — Organizations that foster a growth mindset and support employees with CPDs are better able to adapt to changing work demands
- Positive Company Culture — Investing in people’s growth fosters a supportive, growth-oriented workplace culture.
How do you measure the success and ROI of these CPD initiatives?
Sometimes measuring ROI of CPD initiatives can be difficult and intangible. For this reason, we designed Overalls LifeConcierge differently. Each time an employee uses Overalls to help with a life hassle, we ask them to quantify how much time this saved them at work. This allows our clients to directly measure exactly what the impact is of Overalls on employee productivity. Beyond that, we also track employee satisfaction, productivity, and retention rates.
Looking forward, how do you see the role of CPD evolving in the next 5–10 years?
While CPD has always been important, we are entering an era where CPD will be more important than ever, as AI completely reshapes our economy and how work gets done within organizations. This will require significant reskilling of the workforce to learn how to use AI, and to adapt to a new way of working.
What advice would you give to business leaders who are hesitating to make these changes?
First and foremost, you have every right to be hesitant. There are too many CPD initiatives that over-promise and under-deliver. Companies should be very strategic about their CPD initiatives to ensure that they are not only valuable to the employee, but also advancing a business strategy, and designed in a manner that will foster employee loyalty and productivity. It is always smart to pilot initiatives first and ensure they are achieving the desired effect before rolling out more widely. If you get this right, it will be evident that CPD is a major strategic advantage to your business.
Can you share any upcoming initiatives or plans you have for further investing in your employees?
AI is a major area of professional development where we are currently focused. We have brought on a number of experts in this area while at the same time training our existing team on these emerging technologies. In parallel, as we develop new AI tooling and agents for our LifeConcierge, we are continuously training the concierge team on how to incorporate these tools into their work.
How can our readers follow your work?
Readers can follow Overalls at www.getoveralls.com as well as on LinkedIn.
This was great. Thank you so much for the time you spent sharing with us.
About the Interviewer: Chad Silverstein, a seasoned entrepreneur with over two decades of experience as the Founder and CEO of multiple companies. He launched Choice Recovery, Inc., a healthcare collection agency, while going to The Ohio State University, His team earned national recognition, twice being ranked as the #1 business to work for in Central Ohio. In 2018, Chad launched [re]start, a career development platform connecting thousands of individuals in collections with meaningful employment opportunities, He sold Choice Recovery on his 25th anniversary and in 2023, sold the majority interest in [re]start so he can focus his transition to Built to Lead as an Executive Leadership Coach. Learn more at www.chadsilverstein.com
Investing In Your Employees: Jon Cooper Of Overalls On The Benefits of Offering Continuous… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.