Benenden Health makes COO Appointment

Jon Cawley has been appointed as Chief Operating Officer for the affordable private healthcare provider.

07 August 2025, by Megan Anderson.

Not-for-profit, affordable healthcare provider Benenden Health has appointed Jon Cawley as its Chief Operating Officer. Cawley becomes responsible for the effectiveness of its operations and York HQ employees in delivering services to its 870,000-strong membership.

Cawley joins the private healthcare provider with significant insurance industry experience, having previously held positions as Head of Claims at NFU Mutual, Head of Claims at Towergate Insurance and two Director roles at Zurich Insurance. Cawley previously held the role of Head of Claims Operations for NHS Resolution.

In his new role, Cawley will be responsible for driving the operational strategy for the delivery of Benenden Health’s services to members and its member-facing teams who make up a significant part of 400+ employees at its Holgate Park Drive. York HQ, as well as joining the Society's senior executive team and reporting to the CEO.

Commenting on his new role, Cawley stated, "I am delighted to be joining Benenden Health’s well respected, multi award-winning team. 

"Benenden Health’s values, inclusive approach and clear focus on prioritising our members needs align perfectly with my own aims and experience. I have enjoyed developing innovative, market leading customer experiences across a broad spectrum of customer needs from Motability customers to large corporates and more recently, NHS patients.

"It feels a very natural step to move into the COO role at Benenden Health where I am looking forward to spending time with my team, our members and key partners."

Chief Executive Officer Tom Woolgrove added, "At Benenden Health, the role of Chief Operating Officer is pivotal in ensuring the seamless delivery of our services, driving operational excellence, and therefore maintaining our excellent industry standard for our members.

"Jon not only brings with him a wealth of leadership experience across operations, strategy, and the broader insurance sector, he brings healthcare and change expertise that will be instrumental for our continued growth.

"On behalf of everyone at Benenden Health, we are delighted to welcome Jon to the team and look forward to the positive impact his leadership will have on our members, colleagues, and the wider organisation."