Contract Licensed Insurance Agent

*Resident insurance license in Iowa, Minnesota, Washington, Oregon, South Carolina or Florida*

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

As a Licensed Insurance Agent, you will conduct needs assessments, present plan options, discuss enrollment options across ACA Marketplace and Medicare product lines.

Our call center will be staffed from 9am to 6pm CT, Monday through Friday.

Key Responsibilities

• Handle inbound phone contacts from individuals navigating a loss-of-coverage Special Enrollment Period (SEP) or annual enrollment window

• Conduct thorough needs assessments to determine eligibility for ACA Marketplace plans, Medicare Advantage, Medicare Supplement, or Part D coverage

• Present and compare plan options clearly, ensuring the individual understands benefits, premiums, deductibles, and network considerations

• Document all interactions and enrollment outcomes in the designated CRM platform

• Meet or exceed individual service level, quality, and productivity metrics

• Maintain active licensure in all required states throughout the engagement

• Stay current on plan offerings, carrier guidelines, CMS regulations, and SEP eligibility rules

• Collaborate with non-licensed support staff receiving warm transfers and handing off pre-qualified contacts

Required Qualifications

• Active health insurance producer license in good standing (resident license required in one of these states: Iowa, Minnesota, Washington, Oregon, South Carolina or Florida

• Not currently captive with another insurance agency or carrier

• Minimum 2 years experience selling individual health insurance, ACA Marketplace plans, or Medicare products

• Demonstrated experience conducting enrollment conversations via phone

• Strong working knowledge of ACA subsidy calculations, SEP qualifying events, and Medicare eligibility rules

• Ability to work independently in a remote environment with minimal supervision

• Reliable high-speed internet connection and a quiet, dedicated workspace

• Proficiency with CRM tools and web-based enrollment platforms

Preferred Qualifications

• Active licensure in multiple states

• Experience in a high-volume inbound call center environment

• AHIP Medicare certification (current year preferred)

• Bilingual (English/Spanish) a plus

Contractor Terms

• This engagement is offered on a 1099 independent contractor basis

• You are responsible for your own taxes, benefits, and licensure maintenance costs

• Minimum hours per week will be 20 hours

• This engagement does not constitute an offer of employment and confers no employee benefits

We are an equal opportunity employer. Licensure verification will be conducted prior to contract execution.