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 and email review, scorecards, calibration, and onboarding for every agent, internal or contracted.
• Serve as the escalation point on complex member situations, providing guidance and judgment rather than taking the queue.
• Lead and continuously improve the member support process across technical issues, platform troubleshooting, and non-technical member questions.
• Build the team around you
• Own the hiring strategy and sequencing for the Agency function, including the business case and timing for each role.
• Recruit and develop the agency team and identify gaps in capacity, planning, and enrollment.
• Decide internal versus partner versus contractor for every increment of capacity, and defend that decision on cost, quality, and risk.
• Own partner and contractor capacity
• Own the overflow agency partner relationship end to end: scoping, commercial terms, onboarding, service levels, escalation, and performance review.
• Build and manage the 1099 contract agent network, including sourcing, licensing verification, training, ramp, and seasonal activation. Evaluate BPOs and external agents for capacity planning.
• Hold partner and contractor agents to the same quality and compliance standard as internal staff, with the monitoring to prove it.
• Forecast capacity against open enrollment, Medicare AEP, January 1 ICHRA effective dates, client launches, and reduction-in-force events, and secure committed partner capacity ahead of each.
• Licensing, appointments, and compliance
• Maintain the agency’s 50-state licensure in good standing, including renewals, continuing education, and agent certification cycles.
• Manage carrier appointments, adding carriers as member volume grows in a state and keeping appointment records current.
• Ensure certifications, licensing and appointments are maintained and up to date, work with our principal agent to do so as needed.
• Ensure agent guidance meets CMS Medicare marketing requirements, state producer conduct rules, ACA and ICHRA requirements, and our privacy obligations, supported by a reviewed and versioned guidance library.
• Performance and reporting
• Own the agency KPI framework: speed to answer, abandonment, response time, first-contact resolution, quality, CSAT, productivity, enrollment completion, and COBRA participation rate.
• Own client service level commitments and response time reporting, and act as the approval gate on any service level proposed in a client contract.
• Own application, enrollment, and carrier commission tracking, including reconciliation and revenue forecasting, until the enrollment and commissions analyst is in seat.
• Supply Customer Success with member engagement and COBRA deflection data on a fixed cadence, and drive that measurement toward product instrumentation rather than manual compilation.
• Cross-functional partnership
• Partner with Customer Success on the boundary between the employer and member relationship, including client onboarding requirements, service levels, business review data, and escalation routing.
• Partner with Product and Technology on agent tooling, contact center and CRM workflows, automation, and the digital-to-human handoff.
• Partner with Customer Success and Finance on commission revenue, partner and contractor cost, and the funding and reimbursement workflows that touch member support.

Qualifications

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.
• 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.