While ‘Always Be Closing’ is the sales world’s most famous mantra, a different motto has guided the tech sales career of Carolee Gearhart, Gympass’ Chief Revenue Officer: Always Be Learning.
“I love libraries and technology is a career where there are always new books in the library,” Gearhart says. “There are always so many interesting things happening in this career and there’s always something new to learn.”
This devotion to development shaped her professional trajectory, taking her from smiling and dialing to leading international revenue teams at a high-growth corporate wellness company. It continues to shape how she leads her team, her approach to customers, how she manages talent acquisition, and grows a global company that has already driven more than 250 million visits to Gympass’ fitness and wellbeing partners all over the world.
Career Development
Her journey to the c-suite started with selling telecommunications gear in the ’90s. After a few years slinging routers, hubs and networking equipment, she decided “I want to be building the plan for how we’re doing this. So I went into consulting [at Deloitte], where I decided, no, I actually want to be building the business we’re consulting on, I want to own this progress.”
This led her to the role of Vice President of Global Channels at Peoplesoft, after which she took a multi-year career break to care for a grandfather with Alzheimer’s and grandmother in a wheelchair. This caregiving experience left her with a lasting passion for expanding workplace accessibility that informs how she leads teams to this day.
Gearhart re-entered the workforce at SAP before leading sales teams at Adaptive Insights, GE, and Google. As Google’s Global Channel Chief & Vice President for Global SMB Sales, she handled an $11 billion sales quota and drove triple digit growth. Finally, in 2022, she decided she was ready for her next challenge. That’s when Gympass entered her world.
Why Gympass
There are two things Gearhart needs to see before taking a new position: a personal connection to and passion for the work and a product-market fit. Gympass delivers on both.
Gympass’ goal is to make wellbeing universal. The corporate wellness platform gives employees access to a global network of more than 50,000 gyms, classes, trainers, and wellbeing apps through a monthly subscription. 14,000+ companies (and counting) use Gympass to improve their employees’ work-life wellness and foster happier, healthier, and more productive workforces. Companies that offer Gympass see as much as 40% better retention rates, reducing costly turnover. They can also reduce their total healthcare costs by up to 18% when employees regularly use the benefit, as the company’s research shows Gympass users are three times more physically active than other employees.
The world that emerged from the pandemic aligns with Gympass’ value proposition. Its service — which is flexible, customizable, accessible anywhere, and fosters wellness — meets the needs of our times, Gearhart says. It empowers HR departments to support a newly distributed and often hybrid workforce at a time when only one in four workers think their company cares about their wellbeing, which can drive talent out the door. It simultaneously provides employees with the tools they need to take care of their physical and mental wellbeing, a rising priority for the vast majority – 83% – of workers who believe wellbeing is as important as their salary.
On the personal level, it’s important to her “to sell something where I feel like I’m materially making the world a better place. I’m making people’s quality of life better,” she says. “Gympass had that opportunity in a way that nowhere else I’ve ever been has had. Not only that, Gympass is a company that really lives the mission it is selling, which makes it extremely special.”
The impact she facilitates in this role is exemplified in a client video submitted to Gympass.
“It was an employee who was blind, and he was at the gym with the trainer, which they had set up through Gympass,” she says. “This gentleman shared how impactful it was for him to be able to be in a gym environment where he could work out. That never happened before. And the HR person was saying how this personally touched her, how it’s really changed her to be able to see us serving an employee who had been underserved before. I think that is so meaningful.”
Leading by Example
Dedicated time with her team, facilitating growth, and fostering diversity are core tenets of Gearhart’s leadership philosophy.
Deciding when and how she will connect with her team members is a foundational part of her annual calendar planning. This includes a monthly People Manager call with every manager at any level in her department. In addition to providing a time to connect, she uses it as a venue for internal and external speakers. She recently gave an employee with fading eyesight the floor to give a talk on improving accessibility in the workplace for low-vision workers, and is bringing in a Stanford professor to discuss visibility language.
“It’s the responsibility of every leader to ask: How do we make this a place where folks don’t just feel accommodated, but that they belong? How do we make that effort without being asked?” Gearhart says. “How do I help create an environment that looks more like the communities that we want to serve?”
Cultivating this culture requires a team that will ask questions alongside her, constantly challenging each other to improve. When hiring, Gearhart looks for “culture adds, not culture fits” to ensure she is constantly drawing new ideas and perspectives into the team.
To ensure everyone is managed equitably in a fast-growing, international team, her department leverages frequent development conversations based on predetermined, merit-based criteria.
Driving Bottom-Line Growth
As with every aspect of her work, Gearhart’s approach to increasing Gympass’ impact starts by asking herself questions: “How do we reach more people with the value we offer? How do we speed the time-to-value for them?”
The company’s impact is already growing at an exponential rate. It surpassed a quarter of a billion check-ins to its network partners early this year. The milestone arrived just 18 months after announcing 100 million total check-ins, a growth rate ten times faster today than the company’s first nine years.
The company achieved pandemic-era growth by expanding its services beyond gyms. It incorporated a variety of wellness apps — such as Calm, Stronger U and Strava — and recently announced partnerships with Thrive Global and Headspace.
“We’re looking at how we can help our customers build a more holistic view of well-being,” she says. “That includes not just physical well-being, but also financial and emotional well-being. How can we help people make better choices and live better lives?”
