WTW adds two senior outsourcing sales leaders in North America

NEW YORK, UNITED STATES — WTW has strengthened its North America outsourcing sales team with two senior hires — Alex Holderness as Strategic Account Executive and Tim Oliver as Strategic Sales Executive. 

According to a press release, both join from Alight: Holderness from its multinational client portfolio management practice, Oliver from its healthcare navigation solutions business. 

WTW, a global advisory, broking, and solutions firm operating across 140 countries, places both executives within its Health, Wealth and Career Outsourcing business — a team serving large, complex organizations.

Holderness returns to WTW with 30-plus years experience

Holderness brings more than 30 years in consulting, sales, and product development, including prior roles at WTW in its Employee Experience business before moving to Alight.

At Alight, he managed a multinational client portfolio — providing both enterprise client relationship depth and competitive market perspective.

Rehiring a former WTW employee who then spent time at direct competitor Alight gives the firm both institutional knowledge continuity and fresh competitive intelligence on rival benefits outsourcing offerings.

“Alex brings a unique combination of deep WTW experience and recent market perspective, and we are thrilled to welcome him back to the firm,” said Jill Knoke, Head of North America Outsourcing at WTW.

Oliver brings healthcare and total rewards sales depth

Oliver brings more than 30 years across benefits administration, healthcare navigation, and total rewards strategy — all central to WTW’s outsourcing proposition.

Before Alight, Oliver held senior sales roles at Conduent and Buck Consultants across large-enterprise benefits outsourcing and complex solution sales.

Recruiting two executives from the same competitor — Alight — signals an intentional talent strategy targeting practitioners with direct knowledge of rival client relationships and market positioning.

“Tim’s proven track record in complex sales, along with his strong client focus, will further strengthen our ability to deliver differentiated solutions and drive sustained growth,” said Jill Knoke, Head of North America Outsourcing at WTW.

The benefits outsourcing market in North America has seen growing enterprise demand for integrated Health, Wealth and Career administration solutions as large employers consolidate benefits management under single-provider platforms. 

WTW competes in this market against Alight, Conduent, Fidelity, and other large-scale benefits administrators — companies where both new hires spent decades building client relationships before joining WTW. 

For WTW, the two hires deepen its bench of senior outsourcing sales practitioners as the firm targets larger, more complex employer mandates across health, retirement, and total rewards administration.