# Head of Insurance Operations at When

- Company: When
- What the company does: When Insurance is a technology platform that helps individuals and employers navigate health insurance options during transitions such as job loss or retirement. Backed by Purple Arch Ventures.
- Company website: https://forwhen.com
- Type: Startups
- Level: Principal and up
- Location: United States
- Work setup: Remote
- Posted: 2026-09-17
- Apply by: 2026-11-01
- Apply: https://jobs.ashbyhq.com/when/17b4a4bb-449b-4fe0-a0b4-7f3a662e3ab7
- Page: https://www.1752.vc/careers/jobs/when-head-of-insurance-operations/

## About the role

Every year, tens of millions of Americans go through a coverage transition: a layoff, a resignation, a move into retirement, a 65th birthday while still working. It is one of the most consequential financial decisions a person makes, and it usually arrives as a twenty-page packet during the worst week of their professional life. Nobody owns it. COBRA makes the event compliant; it does not make it managed. That gap is expensive for employers and genuinely hard on people.

## What they're looking for

- Required
- • 10+ years in licensed insurance service operations, with at least 5 years leading teams
- • Health insurance producer licensure held currently or previously, as the foundation for the regulatory judgment this role requires. This is not a selling role
- • Experience scaling a licensed contact center through multiple Medicare AEP or ACA open enrollment cycles
- • Experience managing outsourced, partner, or 1099 agent capacity alongside an internal team
- • Working fluency in Medicare marketing and compliance rules and in ACA individual market and ICHRA enrollment mechanics

Tags: Agency Operations