When Names Kelli Paull as Vice President of Customer Success

[CHICAGO, IL] — August 3, 2026 — When™ (forwhen.com), the workforce transitions platform redefining how employers manage coverage changes, announced today that Kelli Paull has joined the company as Vice President of Customer Success. In the newly created role, Paull will own the post-sale relationship for When’s growing base of employer customers and lead the company’s customer success organization.

When turns the layoffs, exits, and retirements that quietly drive up healthcare costs into savings. When someone leaves a company or ages into Medicare, When intercepts them before they default to COBRA or become high-cost utilizers on the group plan, using an intelligent marketplace platform and licensed, non-commissioned advisors to guide them to individual health insurance plans that genuinely fit their needs and budget. The result for employers: fewer people on COBRA, fewer high-cost claims, reduced COBRA liability, and protected brand reputation—all while delivering an exceptional employee experience for when it matters most.

Paull joins on the back of accelerating enterprise momentum. When is winning larger, more complex employer engagements in a category propelled by record layoff volume, accelerating ICHRA adoption among large employers, and a Medicare-eligible workforce that is the largest it has ever been. As the company scales from dozens to hundreds of employer customers, Paull will define the customer journey, build the team behind it, and connect platform adoption to the outcomes employers care about most: lower COBRA opt-in rates, reduced claims exposure, and measurable ROI.

Reporting to Chief Revenue Officer Brook West, Paull will lead When’s customer success organization—overseeing onboarding, retention, and expansion across the employer customer base and serving as a key voice of the customer in shaping When’s product direction and overall experience.

Paull brings more than a decade of customer success leadership in B2B SaaS technology. She joins When from Outbound AI, where she served as Vice President of Customer Experience. Previously, she served as Vice President of Customer Success at Shyft, a workforce technology company serving Fortune 500 employers. Over a six-year tenure following the company’s Series A funding, she built and scaled the customer success organization to support the company’s growing customer base. Earlier in her career she held customer experience and customer success leadership roles at Valant and business development and sales enablement roles at Merge Healthcare, now Merative. She holds degrees from Montana State University and Seattle University and is based in the Seattle area.

“I’ve had the privilege of working alongside Kelli before, and there is no one I trust more to build this function. Kelli builds customer success teams that genuinely delight customers while driving the retention and expansion that a company like ours runs on. As we scale from dozens to hundreds of employer customers, she brings the rare combination of executive presence, commercial discipline, and a builder’s mentality that this moment demands. I couldn’t be more excited to have her on the team.”

Brook West, Chief Revenue Officer, When

“When exists to make one of the most stressful transitions in a person’s life dramatically easier, while delivering real, measurable value to the employers we serve. As we grow, keeping that promise to every customer is everything—and that’s exactly why bringing on a customer success leader of Kelli’s caliber is such an important milestone for us. Kelli shares our conviction that doing right by employees and delivering hard ROI to employers aren’t in tension; they’re the same win. We’re thrilled to welcome her.”

Andy Hamilton, Co-founder & Chief Executive Officer, When

“What drew me to When is the chance to build a world-class customer success organization from the ground up—defining the experience customers should expect from the first sales conversation, through implementation and go-live, across every renewal, and beyond. Great customer success is about anticipating what customers need and consistently raising the bar for them, and I’m energized to do exactly that here. My approach is simple: be confident yet humble, gather all inputs big and small, and take swift action in the best interest of all. When’s clients are navigating one of the most important moments in their people’s working lives, and when we get that experience right, those customers become our strongest advocates.”

Kelli Paull, Vice President of Customer Success, When

About When

When™ is the workforce transitions platform redefining how employers manage coverage changes. The layoffs, exits, and retirements that quietly drive up healthcare costs, When turns into savings. When someone leaves or ages into Medicare, When intercepts them before they default to COBRA or become high-cost utilizers on the group plan; its intelligent marketplace platform and licensed, non-commissioned advisors guide them to individual health insurance plans that genuinely fit their needs and budget. With fewer people on COBRA, employers experience fewer high-cost claims, reduced COBRA liability, and protected brand reputation—all while providing an exceptional employee experience for when it matters most. To learn more, visit forwhen.com.

Media Contact

Colin Koerin

colin.koerin@forwhen.com