30 Smartest Companies to watch 2019


At PayFlex, we make it simple to plan, save, and pay for personal well-being

PayFlex was founded in 1987 to support pre-tax heath care accounts. PayFlex pioneered the first platform that combines benefit financial accounts, wellness and eligibility management all in one place. Through innovation and technology, PayFlex offers unique account-based and financial wellness solutions with an obsession on the consumer experience.

In dialogue with Michael DiSimone, President and CEO

What is your company’s unique selling point?

PayFlex’s purpose is “To make it simple to plan, save, and pay for personal well-being.” Through this purpose every product and service we deliver to consumers seeks to simplify their experience with saving and paying for health care. Today, we have a unique value proposition to optimize the value of each dollar our members are saving and paying for health care through exclusive discounts.

How do you differentiate PayFlex in the market?

We own, operate, and develop our entire core product and digital suite on a streamlined technology platform. This allows us to efficiently develop, enhance, and innovate around the entire benefit offering. Many of our competitors boast strength in one product or another, but few have a fully integrated offering at the highest security rating in the industry. We set the gold standard for security, with an ‘A’ security rating from SecurityScorecard, which we know is top of mind and critically important to our clients, members and channel partners.

Do your product offerings encourage innovation for the consumer through versatility, usability, and efficiency?

Versatility, usability, and efficiency are table stakes for our core product offerings. We operatewith an agile methodology that accelerates the design and continued development of our product and services. As part of our standard practice, we continually invest in innovative technology solutions, which help us fuel ideation, research, and development that is focused on delivering a superior consumer experience.

What is your risk tolerance?

We not only have an appetite for risk, we consider it a ‘starter course.’ PayFlex fosters a culture of innovation and regularly nurtures it. 

We encourage experimentation and promote a “fail fast” culture. Yet, we are calculated risk takers. On one hand, we push ourselves to test and learn in a safe environment. And on the other hand, in practice, we are noted leaders in security and compliance for the benefit of our clients and members.

What are the factors that make your brand one of the SMARTEST?

In addition to our unique value proposition to make it simple to plan, save, and pay for personal well-being, we know our clients, and we regularly channel their voice in every aspect of our business. It is their voice that helps to feed our system of product development and innovation driven by out-of-the box thinking and experimentation.

We’re on a mission to fully realize and reinvent the value our brand has to offer by exceeding the expectations of our customers with unprecedented and non-traditional relevant, timely, and meaningful financial well-being solutions.

Share with us some of your case studies that demonstrate your proficiency.

We have excelled in customizing and integrating our portfolio into large channel providers. We have a strong background in offering our core suite so many larger entities looking to gain entrance into our space often seek help and support. 

An example is the partnership that PayFlex recently formed with an East Coast provider that offers a customizable benefits enrollment and administration platform. This partnership enables employers to choose among top providers, like PayFlex, that offer the products, integration and ease of enrollment for their employees. PayFlex is offered on this providers platform because of our knowledge, standard processing, and expert project management allows for this partnership to be fully implemented and functional in just a few months. Our technology is a proprietary platform that enables a channel partner to white-label and seamlessly integrate for a holistic solution including single sign on for members to perform their financial transactions.

Which are the moments when you felt “puffed up with pride”?

The moments that fuel us are when we get unsolicited praise from our clients and members.  For example, our recent digital enhancements we launched – an HSA calculator and a bar code scanner for eligible health care products within the PayFlex Mobile® app – have received high praise.

Our HSA calculator imports our members’ relevant data from their online PayFlex account to make it easy for the member to simulate how their money can grow over time. The calculator illustrates how much tax savings can be realized, how yearly compounding and continual contributions can grow an HSA balance, and how investing in mutual funds can further accelerate the amount of savings that can be realized to pay for future health care expenses.

The launch received accolades, like “These types of enhancements are making positive impacts to our clients, and they are taking notice” and “I just wanted to tell you that I’m playing around with this new HSA calculator, and it’s AWESOME!  I’m definitely going to be using this in our retirement workshops and additional training we provide. As you know, we’re really passionate about financial wellness, and we’re looking for ways to educate and motivate our employees to take the actions they need to be financially secure now and in retirement.” Receiving these comments makes us proud knowing we are providing relevant and tangible tools for our clients and their members.

An in-app bar code scanner is planned to launch next and will allow members to scan products on store shelves or in their home to determine if they are eligible to purchase through their Health Savings Account or Flexible Spending Account. We’re taking the guesswork out of the equation for the member.

We take great pride in building convenient support tools that help educate our members and provide more value for the dollars they spend on health care. Providing a simplified and optimized user experience on our digital platforms is one of our guiding principles, and we’re pleased to continue releasing new features to meet our customers’ needs.

Is your organization pursuing growth and new business/market development with as much passion as it does operational efficiency?

This is an area where we’ve hit the igniter switch. We see the opportunity to reinvent how and who we serve with our core capabilities. As an example, there’s an incredible opportunity to help people improve their total financial health picture that is both meaningful and tangible and fits into their daily life. We’re investing heavily in both intellectual and technological properties to pursue truly disruptive consumer solutions beyond our current market today.

About Michael DiSimone

As the President and CEO of PayFlex, Mike leads the organization’s strategy and operations across its portfolio of health care financial services. He’s leading PayFlex into its next chapter delivering personalized health care solutions to educate, guide and support PayFlex members on their path to financial well-being. Mike is most passionate about helping people achieve their health ambitions, optimizing their health care dollars and delivering an exceptional service experience to each member. Prior to leading PayFlex, Mike served as the VP, Global Business Solutions for Human Resources at Aetna, where he led employee service delivery functions, serving 50,000 employees globally. Responsibilities in this role included Employee Relations, HR Policy & Compliance, M&A, HR Finance, HR Analytics, and strategy. At the same time, Mike served as Head of HR for the Global Finance organization and the Global Operations & Technology organization.

Mike holds a BBA in accounting and an MBA in finance from Pace University, and he completed executive education programs in General Management and Leadership at Columbia Business School. Mike and his family enjoy spending time together, going to the theatre, and participating in a variety of community events.

“There’s an incredible opportunity to help people improve their total financial health picture that is both meaningful and tangible and fits into their daily life.”

“We’re passionate about what we do and help consumers achieve financial stability through education, digital resources and an intuitive member website.”