Insurance Operations Leader, Licensed Agency (Remote)

When; United States; Remote; USD 180,000 - 260,000; Full time

Benefits offered by this job

Health insurance

Stock options

Job summary

When is the enterprise platform for guided health insurance decisions at every qualifying life event. We are hiring a Head of Insurance Operations to lead the licensed agency function, guide Medicare and ICHRA enrollment, and design scalable capacity and compliance models.

You will inherit a small team of licensed agents, manage partnerships, and build the in-house and contractor capacity framework to support growth and regulatory defensibility across states.

Qualifications

• 10+ years in licensed insurance service operations with leadership experience.
• Health insurance producer licensure as the foundation for regulatory judgment.
• Experience scaling a licensed contact center through Medicare AEP or ACA cycles.
• Experience managing outsourced, partner, or 1099 capacity alongside internal teams.
• Fluent in Medicare marketing rules and ACA ICHRA enrollment mechanics.
• Familiarity with agency licensing and carrier appointment operations.
• Strong ability to define KPIs, build dashboards, and drive decisions.
• Experience hiring into a function you are building; ramping and onboarding.
• Excellent communication and high emotional intelligence.
• Comfortable operating in an early-stage environment.

Responsibilities

• Lead the existing licensed agent team including scheduling, coaching, and performance.
• Own member support experience across phone, email, and chat with escalation paths and enrollment workflows.
• Run QA and training, including call/email review, scorecards, calibration, and onboarding.
• Serve as escalation point on complex member situations; provide guidance and judgment.
• Improve member support processes for technical issues and platform troubleshooting.
• Own hiring strategy and sequencing for the Agency function; build the team over time.
• Recruit and develop agency and contractor capacity; define internal versus partner vs contractor.
• Own overflow agency partner relationships end-to-end; terms and performance reviews.
• Forecast capacity for enrollment periods and secure partner capacity in advance.
• Maintain licensure across states and ensure compliance with regulations.
• Manage carrier appointments and keep records current; ensure certifications stay up to date.

Skills

Insurance operations

Licensure

Contact center scaling

Contractor management

Medicare & ACA knowledge

Licensing & appointments

KPIs & dashboards

Hiring

Communication

Startup mindset

Education

Bachelor’s degree or equivalent

Tools

Zendesk

HubSpot

Metabase

Job description

When is the enterprise platform for guided health insurance decisions at every qualifying life event. We are hiring a Head of Insurance Operations to lead the licensed agency function, guide Medicare and ICHRA enrollment, and design scalable capacity and compliance models.

You will inherit a small team of licensed agents, manage partnerships, and build the in-house and contractor capacity framework to support growth and regulatory defensibility across states.