Fortune 500 life insurance company MassMutual has a storied past: In business for nearly 175 years, the organization predated the Civil War and survived through massive and rapid evolution in the American business landscape. Today, MassMutual employs about 6,200 U.S. employees and offers a range of financial products and services.
The organization’s capacity to thrive over such an expansive timeframe speaks to its embrace of continuous improvement and adaptability, particularly in the HR space, says Cindy Ryan, MassMutual’s head of HR. While the function has a deep willingness to respond to change, it has long done so through the lens of organizational purpose, she says, an approach that has been pivotal to its ability to sustain HR innovation—and was critical to Ryan’s own decision to join MassMutual in 2024.
Ryan, who spent more than two decades at Cigna, recently spoke with HR Executive about what continues to fuel MassMutual’s HR innovation.
Ryan: The move to MassMutual was an opportunity to work for a mutual company that is centered around its purpose—to help people secure their future and protect the ones they love.
To me, being in a company where I could continue to evolve an HR strategy aligned to the business strategy—built around this strong purpose—was very compelling to me.
HR Executive: Given MassMutual’s rich history, what are both the challenges and opportunities of pursuing HR innovation at an organization with such an established legacy?
Ryan: Like any company, it’s important we continue to ensure we’re staying abreast of all the key trends in the marketplace and balancing business needs with employee needs. One of the misnomers about well-established companies is that they’re rooted in their ways. Yet, I would argue that well-established, well-performing companies have had to continually innovate and find new ways of doing things to stay relevant. That speaks to the company’s longevity and its ability to be successful in multiple business cycles over a period of many years.
In the HR space, I don’t view that as a challenge, but rather an opportunity in terms of our ability to try different things and be a thought leader in a variety of HR areas. Benefits and wellness are where we have been and continue to be a thought leader before other employers.
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HR Executive: When it comes to benefits, how can HR balance the needs of incoming, younger workers with those of other generations?
Ryan: The benefits lever is one of the most important ways to do that. The way we’ve approached it is by listening to our employees through surveys and focus groups. [It’s important to have] benefits programs that allow for personalization and individualization—offering a broad range of unique benefits to meet people at all life stages. For example, we have a “wellbeing wallet,” which our employees value and utilize: We give each employee a set amount of money annually they can use for specific wellness needs—physical, mental and financial. They can choose how to use it. Since implementing the wellbeing wallet in 2023, we have paid out over $5 million via this benefit. It’s a great example of how different generations are using our benefits for their specific health and wellness needs; Gen Z employees, for example, tend to use it in different ways than older generations. Having that wide range of diverse benefits is appealing to a multigenerational workforce.
HR Executive: What do HR leaders need to keep on their radar as the new presidential administration goes forward?
Ryan: HR leaders need to continue to keep an eye on what’s happening in the external environment, understand their workforce dynamics and stay true to their company’s purpose, mission and business strategy—and find the right balance of all these factors.
HR Executive: What big-picture impact do you hope your career has had on the organizations you’ve worked with?
Ryan: I’ve been very fortunate in my career to have had leaders invest in me and provide me with great development experiences. And they often saw things in me when I didn’t see them myself. They had confidence in me and provided me with opportunities, stretch assignments and coaching, which gave me a strong foundation upon which to build my career. What I have done and continue to do is pay it forward by coaching and providing cross-functional experiences to people in my organization and across the companies I’ve worked with. I hope my legacy is the number of people who say I contributed to their development and had confidence in them, when they may not have seen it within themselves.
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