I must engage with clients and frontline team members to help Benenden Health expand.
The CEO of Benenden Health, Tom Woolgrove, leads an organization that serves more members than any other healthcare provider in the UK.
As a former amateur player in both rugby union and league, it’s fitting that Tom Woolgrove, the head of Benenden Health, describes leadership as closely resembling a contact sport.
With over three decades of experience in the financial industry, Woolgrove has cultivated a unique leadership style that draws from a diverse set of skills. This led him to take charge of the not-for-profit healthcare organization in October, which serves nearly 900,000 members.
“Visibility is key; being present with your customers and frontline staff is essential to grasp how the business functions,” Woolgrove emphasizes. “Avoid isolating yourself, as this approach will yield greater success.”
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Operating primarily out of St Albans, Woolgrove dedicates most of his workweek to Benenden Health’s York headquarters or its main hospital in Benenden, Kent, which was originally a tuberculosis sanatorium. The organization is poised to commemorate its 120th year in 2025.
“There’s a tangible history and commitment to a member-focused ethos in many mutuals, especially one established as long ago as ours,” he states.
“This history is a strength; we bear the responsibility of safeguarding it and ensuring our presence for another century.”
Benenden Health’s primary hospital is located in Kent, with members gaining access to over 500 facilities for diagnostics and more than 40 for treatments.
“The goal is to evolve and expand. Past success doesn’t guarantee future advancements.”
As he completes six months as CEO, Woolgrove expresses his focus on “continuous improvement rather than drastic changes.”
“Our member demographic is shifting,” he points out. “Attracting new members, potentially from different backgrounds, is key. It’s about harmonizing our rich history with a forward-looking perspective.”
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Woolgrove’s impressive background encompasses his roles as CEO of Premium Credit, CTO at the Bank of Ireland, and managing director of UK Personal Lines at Direct Line Group and Halifax Insurance. He also held the presidency of the Chartered Insurance Institute.
“In various organizations, I’ve had to adjust my leadership style to effectively deliver results,” he acknowledges. His visible leadership approach was particularly emphasized during his time at Halifax.
“Successful retailers often maintain a connection to their frontline staff, who are deeply aware of customer needs. This engagement has greatly informed my understanding of what our members seek.”
Benenden Health actively participates in various community events across the UK.
“Mutual organizations operate commercially like any other business. Our success metrics may differ, but fundamentally, we must remain commercially viable as stewards of our members’ contributions.”
Woolgrove aims to elevate the Benenden brand’s visibility amidst larger competitors, asserting that its membership plan is “an excellent and competitively priced option.”
“Companies can provide the same rate, around £15.50 per month for their employees, granting them access to around-the-clock GP services, diagnostic testing, and treatments.”
“We do not underwrite claims medically, and premiums remain stable, embodying the mutual principle of affordable healthcare for everyone.”
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Inclusivity is a cornerstone of Benenden Health’s Diversity, Equity, and Inclusion (DE&I) initiatives, which were established prior to Woolgrove’s tenure. He plans to enhance inclusivity in the workplace further, contrasting with trends in the US government under President Donald Trump.
“The UK is predominantly a diverse and inclusive nation, while it seems the US has become increasingly divided,” Woolgrove observes.
“Although we don’t operate in the US, companies with US branches are facing interesting dynamics. Being inclusive and catering to a diverse member base is central to our mutuality.”
Benenden Health’s CEO is steering an organization dedicated to enhancing its DE&I strategies.
“Fostering a diverse and inclusive workforce means ensuring everyone feels connected and invested in the organization.”
Woolgrove references a guiding principle from his time at Direct Line: ‘Encourage all staff to express themselves at work.’ “We aimed to create an environment where individuals could be themselves without feeling the need to tone down their personality,” he shares.
“Maximizing our colleagues’ potential is essential, as we should also embody the diversity of our membership within the organization.”
With digital sales representing 80% of new business at Benenden, the organization, which employs 800 people, aspires to reach 1 million members.
“This focus is about propelling the organization to operate swiftly while identifying opportunities,” notes Woolgrove. “One key challenge lies in enhancing visibility and awareness to reinforce our position as challengers in the market.”
Understanding leadership
I almost enlisted in the army, where I gathered that effective leadership often revolves around serving and empowering those below you.
Tom Woolgrove, seen here at Benenden’s primary hospital in Kent, exemplifies ‘visible leadership’.
My initial industry role was with Halifax Bank of Scotland. Andy Hornby, despite mixed reviews, taught the importance of maintaining visibility across all branches and truly understanding operational challenges. He effectively used those insights to implement meaningful changes, focused on enhancing customer experiences.
The organization had a relatively flat structure, emphasizing empowerment within business units, a principle that continues to resonate with me today.
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