# Director, Member Services 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: USA
- Work setup: Remote
- Pay: $150K to $170K base salary per year (USD)
- Posted: 2026-11-06
- Apply by: 2026-12-21
- Apply: https://jobs.ashbyhq.com/when/0aa7968b-507d-4caf-9588-ae2aeb9338e1?utm_source=1752vc&utm_medium=careers
- Page: https://www.1752.vc/careers/jobs/when-director-member-services-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. Found on 1752vc Careers, the job board for startup and VC roles.

## What they're looking for

- 8+ years in customer support or contact center operations, including 4+ years leading teams
- Strong technical skills: hands-on with Zendesk or a similar platform, workflow automation, and reporting tools, and comfortable using AI-assisted support tools
- Highly analytical: comfortable defining KPIs, building dashboards, and turning performance data into operating decisions
- Experience in health care, digital health, health insurance, benefits, or another health-related setting
- Experience with capacity planning for volume that changes through the year

Tags: Agency Operations

Source: 1752vc Careers, https://www.1752.vc/careers/jobs/when-director-member-services-operations/