Health Insurance Enrollment Counselor (Remote, Part-Time)

About the Organization

Ask Ariana is an organization that offers free help getting access to affordable healthcare to folks across California.

About the Role

We’re looking for people who love the idea of helping folks to find the health plan that meets their individual needs. This is a part-time, W-2, 100% remote role (anywhere in California).

The work involves:

• Explaining the details of Covered California health insurance plans
• Taking scheduled phone calls from current and prospective clients
• Understanding people’s healthcare and emotional needs
• Communicating complex information in a clear and friendly way
• Taking accurate notes and updating client records
• Lots of regular communication with team members via Slack

Compensation starts at $20/hour during Summer training and shifts to $23/hour upon completion of training in Fall.

Timeline

July: Applications close. Ask Ariana team reviews applications and interviews candidates.

Early August: Candidates will be offered positions. Licensure coursework and on-the-job training begins.

August and September: candidates can expect to be paid $20/hr for 5 hrs/wk of on-the-job training with us, and should plan to work on their licensure coursework for 15/hrs/wk concurrently. Expect to be engaged in 20/hrs/wk total of both unpaid studying and paid training during August and September.

October: if you’ve completed the 50 hours of coursework, 40 hours of on the job training, and are a good fit for the job, we’ll bump you to $23/hr and you can expect approximately 20-30 hrs/wk of work clear through the end of January!

If you’re a great fit, we’re open to hiring someone for a part-time, year-round position 🙂

Job Duties and Responsibilities

Enrollment Duties Can be done between 8am and 7pm any day of the week. At least 15 weekday hours of availability are required during Open Enrollment period October-January

• Conduct client enrollments and renewal appointments over the phone (each call requires a 60-minute commitment)
  • Educate clients on financial assistance (APTC)
  • Educate clients on the different metal tiers of health plans
  • Explain the costs and co-pays of basic medical visits
  • Use available resources to navigate complex issues and questions
  • Compassionately listen to the client's health needs and history to guide them to the correct plan and carrier
• Submit applications through the Covered California enrollment portal with accuracy and attention to detail
• Troubleshoot client's access to their Covered California online account
• Process online payments, as needed

Admin Duties: Admin tasks can be done any time throughout the day, preferably between 9am and 6pm M-F

• Create profiles using a CRM
• Create detailed notes about client interactions using a CRM
• Navigate a cloud-based help desk platform to send and receive emails, texts, and calls
• Send emails, calls, and texts for a variety of tasks daily
• Respond to inbound inquiries in a timely manner including calls, texts, and emails
• Upload a variety of documents to the Covered California portal on clients’ behalf
• Call the Covered California Agent Hotline and health insurance company hotlines to troubleshoot a wide range of issues on clients’ behalf
• Hand-write birthday cards and thank-you notes

Requirements

• Located in California
• Available at least 4 weekdays, with some evening/weekend availability
• Correspond with the team using Slack throughout the day
• High emotional intelligence
• Personable over the phone
• Excellent writing skills
• Analytical skills
• Computer literacy
• Highly organized, timely, and self-motivated
• Attend a weekly team meeting via Google Meet
• Reliable internet connection
• California Insurance Agent License (see below for License Support Program details)

Perks

• Build your own schedule (15 - 30 hours/week)
• Remote work
• Supportive and collaborative team
• Feel-good work (our clients are so grateful!)
• Annual company retreat
• Queer supportive space
• Neurodivergent supportive space

How to Apply

To apply for a position at Ask Ariana, please fill out this form: application form 2026

Licensing Support Program

If you don’t already have the California Life and Health Insurance license, we are setting up a program to help qualified applicants get licensed. Here’s how it works:

• If you are selected as a License Candidate after our interview process, you will be offered a spot in our self-directed licensing support program.
• We’ll pay for your coursework! In exchange, we expect that you’ll complete 50 hours of coursework from August till early September (about 15/hrs/wk, unpaid), and then study for and take the licensing exam by the end of September.
• We want agents to be ready to hit the ground running for the start of our busy season on October 1.
• You can also anticipate 5hrs/wk of paid on the job training during August and September. Please consider this candidate position to be a 20hr/wk commitment for the majority of August and September.
• After you complete the coursework, you will need to pass an in-person proctored exam and a fingerprint check in order to obtain the license. You’ll need to register and pay for those things on your own (approximately $400).
• If you complete these steps and successfully receive your California Health Insurance Agent License, you’ll receive a $500 bonus and we’ll reimburse you for the exam/fingerprinting cost.
• In sum, if you complete the course and get licensed, you’ll finish September with your entire licensure paid for by Ask Ariana (except for your hours spent on coursework and studying).

Important things to understand about the licensing support program:

• While we pay for the coursework, you’ll need to pay for the exam itself; only do this if you are confident you’ll pass. We do not offer reimbursement for failed exams.
• If you pass our interview process and pass the exam, you’ll get the bonus & reimbursement regardless of whether we make you an offer…or whether you accept it.

• Build your own schedule (15 - 30 hours/week)
• Remote work
• Supportive and collaborative team
• Feel-good work (our clients are so grateful!)
• Annual company retreat
• Queer supportive space
• Neurodivergent supportive space
• 401(k) matching
• Paid sick time
• Bonus for completion of Open Enrollment

Spanish-language skills are a huge plus!