The Hidden Cost of Offboarding - Andrew Hamilton

The Hidden Cost of Offboarding: Why the Employee Exit Matters More Than Most Leaders Think Most organizations obsess over the employee experience while people are inside the business. Then someone leaves, and the strategy often disappears. That disconnect can create more than a poor final impression. It can expose the organization to unnecessary cost, risk, and reputational damage. In this episode of the People/AI Strategy Forum, Sam Reeve, CEO of CompTeam, speaks with Andrew Hamilton, CEO and Co-Founder of When, about why offboarding should be treated as a strategic business issue rather than an administrative afterthought. Andrew explains how traditional COBRA practices can leave former employees navigating complex healthcare decisions with limited support, while employers may continue carrying significant claims exposure after those employees have left the organization. The conversation explores how organizations can rethink benefits transitions, severance support, and the end of the employee lifecycle to create better outcomes for both employees and the business. Sam and Andrew discuss: • Why the employee experience should extend beyond the final day of employment • How COBRA can create unexpected financial exposure for employers • Why traditional COBRA subsidies may not always be the most effective way to support departing employees • How AI can help individuals compare healthcare options and make more informed decisions • Why human guidance remains important in complex benefits decisions • How portable benefits may become more important as careers shift between traditional employment, independent work, and the gig economy • Why HR, finance, and benefits leaders should view offboarding as part of broader workforce and risk strategy The core message is simple: the employment relationship may end, but the financial, cultural, and reputational impact of that exit can continue. For CEOs, CFOs, CHROs, and benefits leaders, improving the exit experience is not only about supporting people. It is also about making smarter business decisions. Learn more about When: https://forwhen.com If your organization is rethinking employee experience, benefits strategy, workforce costs, or how to better align people decisions with business performance, CompTeam can help. Learn more about CompTeam and schedule a conversation with Sam Reeve: https://compteam.net If you enjoyed this episode, follow the People/AI Strategy Forum on your preferred podcast platform and join the conversation!  About the People/AI Strategy Forum The People/AI Strategy Forum explores how leaders navigate the intersection of people strategy, leadership, and artificial intelligence. Hosted by Sam Reeve, Founder & CEO of CompTeam, the Forum features conversations with executives, practitioners, and experts shaping the future of work. Learn more about CompTeam and the People/AI Strategy Forum at compteam.net.