Shannon Schafer is VP of Sales at Healthpilot, where she leads the sales, customer experience, and operations teams that guide people through one of the most consequential and least understood decisions of their working lives: the transition into Medicare. Her teams have helped thousands of beneficiaries navigate aging in, retiree coverage changes, and carrier disruptions — giving her a direct view into where employees get stuck, what they get wrong, and what the fallout looks like for the HR teams supporting them. With a career spanning insurtech sales and service leadership, Shannon brings a practical perspective on how employers can support Medicare-eligible employees and retirees without adding burden to their benefits teams.