Director, Member Services Operations

The posting, as When wrote it

The Opportunity

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.

When is the enterprise platform for guided health insurance decisions at every qualifying life event. Through When Choice, When Medicare, and When ICHRA, we combine an intelligent decision-support experience with licensed, non-commissioned agents so every person understands their real options and lands somewhere good. We have supported more than one million employees and managed over 204,000 qualifying events for Fortune 50 and Fortune 500 employers, reducing COBRA enrollment by up to 80% while improving the experience for the people leaving. Doing right by employees and taking cost out are usually opposing forces. Here they are the same action.

Role Overview

We are hiring a Director, Member Services Operations: an operational expert who executes and scales member services through tools, data, and automation while delivering a superior member experience. You will lead the Member Services team: the licensed agents who guide members through coverage transitions, ICHRA enrollment, and Medicare decisions, along with specialists in enrollment, licensing, and other key roles as we grow.

This is a hands-on role on a team that runs today, and scale is the focus. You will manage quality and capacity, build the processes, tools, and automation that let the team handle more volume without losing quality, and use data to make decisions as volume grows.

How We Staff the Agency

When’s internal agent team is lean by design. We do not intend to build a large in-house contact center. A handful of full-time licensed agents carry our core member experience, set the quality bar, and handle our most complex situations. Everything above that baseline, including open enrollment peaks, large client launches, reductions in force, Medicare, and new ICHRA volume, is met through our agency and potentially via overflow agency partners and 1099 contract agents.

Capacity planning, partner management, and quality control across a blended workforce are therefore central to this role. Success is not measured by the size of the team you build. It is measured by whether members get excellent, compliant guidance regardless of who is on the other end of the call.

Responsibilities

Lead the existing team

• Manage When’s full-time licensed agents, including scheduling, coaching, and performance management.
• Own the member experience across phone, email, and chat, including outreach cadence, scripts, escalation paths, and enrollment workflows.
• Run quality assurance and training: c

[…]
e that measurement toward product instrumentation rather than manual compilation.

• Partner with leadership on how Member Services scales as volume and products grow.

Qualifications

Required

• 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.
• Experience managing outsourced, partner, or 1099 agent capacity alongside an internal team.
• Excellent communication, high emotional intelligence, and the ability to make complex health insurance topics simple.
• Effective in an early-stage environment: strategic when it matters, hands-on by default.

Strongly preferred

• Familiarity with HubSpot and business intelligence tools such as Metabase.
• Experience standing up a quality assurance program from scratch rather than inheriting one.
• Bachelor’s degree or equivalent relevant experience.

Reporting and Team

This position reports to When’s Co-Founder. You will lead the Member Services team and, as When grows and scales, build it out with roles such as an enrollment specialist, a licensing specialist, and other key roles. You will work closely with Customer Success, which owns the employer relationship. The Agency function owns the employee and member relationship, and the two work in close partnership.

Compensation, Location, and Travel

We offer a competitive salary ($150,000 to $170,000), we pay 100% of your health insurance, stock options and more. This role is remote, with minimal travel for company and occasional client meetings.