Tom Cox - When - The AI Workforce Transitions Platform

Tom Cox

Channel Sales Manager

Tom Cox is Channel Sales Manager at When, where he focuses on building strategic partnerships with TPAs, Health Plans, and COBRA administrators to modernize workforce transitions through AI-powered solutions. With over 20 years of experience in benefits administration technology, Tom has built a career architecting and scaling channel sales programs that drive revenue and accelerate market penetration. His background includes leadership roles at WEX Health, Alegeus, and other healthcare technology companies. Tom specializes in translating complex technology into clear business value and is passionate about how AI is transforming HR functions, benefits technology, and the employee benefits experience.

Insight

May 21, 2026

The Captive Blind Spot at the Exit Door

Tom Cox](/content/explore/blog/captive-insurance-blind-spot-at-exits/index.html)

Insight

May 19, 2026

Benefits Consultants, the 2027 Renewal Math Is Already Brutal. Here Are the Two Levers That Actually Move the Number.

Tom Cox](/content/explore/blog/levers-brokers-can-pull-during-renewals/index.html)

News

Apr 8, 2026

P&A Group Partners with When to Deliver Healthcare Transition Support for Employer Clients

Tom Cox](/content/explore/blog/p-a-group-partners-with-when/index.html)

Insight

Mar 17, 2026

AI in Employee Benefits: From Chatbot Curiosity to the Most Important Decision Your Departing Employees Will Ever Make

Tom Cox](/content/explore/blog/ai-in-employee-benefits/index.html)

Insight

Mar 2, 2026

COBRA Is a Known Underwriting Problem. When Is the Solution Carriers Haven't Had.

Tom Cox](/content/explore/blog/cobra-is-a-known-underwriting-problem/index.html)

Insight

Jan 20, 2026

How Self-Funded TPAs Can Help Clients Reduce COBRA Claims Exposure

Tom Cox](/content/explore/blog/how-self-funded-tpas-can-help-clients-reduce-cobra-claims-exposure/index.html)

Insight

Jan 20, 2026

COBRA Is Your Most Underleveraged Service Line — How Benefits TPAs Can Change That

Tom Cox](/content/explore/blog/cobra-is-your-most-underleveraged-service-line-%E2%80%94-how-benefits-tpas-can-change-that/index.html)