Head of Insurance 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 Head of Insurance Operations to lead the licensed agency function at When: the agents who guide members through coverage transitions, ICHRA enrollment, and Medicare decisions, and the operating infrastructure that makes that guidance possible.

This is an execute and build role on top of a working team. You will inherit a small team of licensed agents and an operation that runs today, and you will design what comes next: the enrollment function at When, the in-house, partner and contractor capacity model, and the compliance discipline that keeps our guidance defensible in every state including licensing and certifications.

How We Staff the Agency

When’s internal agent team is small by design and will stay that way. 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 support experience across phone, email, and chat, including outreach cadence, scripts, escalation paths, and enrollment workflows.
• Run quality assurance and training: call a

[…]
t 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.
• Familiarity with agency licensing and carrier appointment operations, including NIPR or Sircon workflows.
• Highly analytical: comfortable defining KPIs, building dashboards, and turning performance data into operating decisions.
• Experience hiring into a function you are building, including writing the role, making the case, and ramping the person.
• 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

• Background at an FMO, BGA, carrier direct-to-consumer or individual market service organization, or a licensed agency operating at national scale.
• Experience with coverage transitions, COBRA or Medicare, qualifying life events, or employee benefits administration.
• Familiarity with Zendesk, 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 inherit a small team of full-time licensed agents and build a management layer beneath you over the first year. The Agency function owns the employee and member relationship; our Customer Success organization owns the employer relationship, and the two work in close partnership.

Compensation, Location, and Travel

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