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Remote Open Enrollment Jobs in Chicago, IL (NOW HIRING)

Harmony Health Plans Inc

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Licensed Health Agents - 1099 Remote | Leads Provided

Chicago, IL · Remote

$5.0K - $25K/mo

... remote - work from anywhere - You own your book - every customer you enroll is yours to keep What ... Open Enrollment runs November 1 - January 15. The weekly advance is an advance - subject to ...

Allied

Associate Client Executive

Chicago, IL · On-site +1

$72K - $75K/yr

Act as a client-facing representative, providing support during open enrollments, independently ... Remote Here at Allied, we believe that great talent can thrive from anywhere. Our remote friendly ...

Allied

Benefits Eligibility Specialist

Chicago, IL · On-site +1

$20 - $21/hr

Processes changes, renewals, and open enrollment in all eligibility technology platforms ... Remote Here at Allied, we believe that great talent can thrive from anywhere. Our remote friendly ...

Embarc Advisors

People Operations Manager

Chicago, IL · Remote

Coordinates open enrollment, benefits changes, and leave administration in partnership with the PEO ... remote work environment, supported by structured operations (EOS) to keep us aligned and ...

Embarc Advisors

People Operations Manager

Chicago, IL · Remote

Remote (applicants residing in Mountain and Central time zones are preferred) The People Operations ... Coordinates open enrollment, benefits changes, and leave administration in partnership with the PEO.

Aeroflow

HRIS Analyst

Chicago, IL · Remote

Aeroflow Health - HRIS Analyst Remote Opportunity Aeroflow Health is a national leader in home ... Configure and support annual Open Enrollment, benefit life events, testing, and troubleshooting.

Aoglobelife

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Remote Customer Sales Rep Entry Level (No Experience Welcome to Apply)

Chicago, IL · Remote

$60K - $80K/yr

... enrollment * Maintain accurate customer records within company systems * Follow up with clients ... Are open to learning and receiving coaching Candidates with experience in customer service, retail ...

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All JobsOpen Enrollment JobsRemote Open Enrollment JobsRemote Open Enrollment Jobs in Chicago, IL

Remote Open Enrollment information

See Chicago, IL salary details

$27.8K

$79.7K

$121K

How much do remote open enrollment jobs pay per year?

As of Aug 26, 2026, the average yearly pay for remote open enrollment in Chicago, IL is $79,722.00, according to ZipRecruiter salary data. Most workers in this role earn between $42,200.00 and $120,000.00 per year, depending on experience, location, and employer.

What is the difference between Remote Open Enrollment vs Remote Benefits Coordinator?

AspectRemote Open EnrollmentRemote Benefits Coordinator
Required CredentialsKnowledge of benefits plans, HR policiesCertifications like CEBS or CBP often preferred
Work EnvironmentPrimarily administrative, online platformsCustomer service, communication with employees
Employer & Industry UsageUsed during open enrollment periods in HR/benefits departmentsPart of HR teams managing employee benefits year-round
Search & Comparison IntentFocuses on open enrollment processes and schedulingInvolves ongoing benefits administration and support

Remote Open Enrollment roles focus on managing benefits enrollment periods, while Remote Benefits Coordinators handle ongoing benefits administration and employee support. Both roles require knowledge of benefits plans, but their scope and timing differ significantly.

What are the most commonly searched types of Open Enrollment jobs in Chicago, IL?

The most popular types of Open Enrollment jobs in Chicago, IL are:

What are popular job titles related to Remote Open Enrollment jobs in Chicago, IL?

For Remote Open Enrollment jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Remote Open Enrollment jobs in Chicago, IL look for?

The top searched job categories for Remote Open Enrollment jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Remote Open Enrollment jobs?

Cities near Chicago, IL with the most Remote Open Enrollment job openings:

Remote Open Enrollment jobs near you
Infographic showing various Remote Open Enrollment job openings in Chicago, IL as of August 2026, with employment types broken down into 80% Full Time, 18% Part Time, and 2% Temporary. Highlights an 100% Remote job distribution, with an average salary of $79,722 per year, or $38.3 per hour.

Licensed Health Insurance Agent -- Remote, $24/Hr + OT + Commission

Thrive Health Benefits

Chicago, IL • Remote

$768 - $1.3K/wk

Temporary

Re-posted 4 days ago

Job description

$24 an hour. Overtime on top during Open Enrollment. Commission on every enrollment, paid weekly. We're hiring remote ACA sales agents — helping families find health coverage they can actually afford, and getting paid properly to do it. This is a seasonal W-2 role (a real paycheck, taxes handled — not 1099). You can start as early as September 1, and Open Enrollment runs November 1 through January 15 — so it's a four-and-a-half-month paid season, not a six-week gig.

What you'll earn

  • Start as early as September 1 — $24/hour base, about 32 hours a week through training and ramp-up (roughly $768 a week)
  • Open Enrollment runs November 1 through January 15 — 50 hours a week, with overtime at $36/hour past 40, or about $1,320 a week in base pay alone + commissions on top of that
  • A note on overtime: overtime rules vary by state. Your overtime eligibility and the hours threshold that triggers it follow the law where you live, and we'll confirm exactly how it applies to you before your first shift.
  • That's roughly $21,000 in base pay from September 1 through January 15, before a dollar of commission
  • Commission on every enrollment, paid weekly, climbing the more you write
  • Extra income from ancillary products and referrals
  • A strong producer can clear $28,000+ across the full September–January season (illustrative, based on consistent production)

Earn before Open Enrollment even starts

  • $300 for every agent you bring. Know a licensed agent? A friend, a former co-worker, anyone. Bring them to our hiring webinar. If they're hired and both of you finish through Open Enrollment, you earn $300 per agent — refer three and that's $900 on top of everything else you make.

What you'll do

  • Work 100% remote, from home
  • Help inbound callers and live transfers enroll in ACA Marketplace plans — no cold calling; we bring you the leads
  • Follow proven, compliant scripts with full training and support

What you need

  • Active E&O insurance and resident/non-resident licenses in FL, TX, and GA
  • Don't have all three yet? Apply anyway. Pass the interview and you'll receive a conditional offer with exact steps to get licensed — and we reimburse up to $375, based on the licenses you obtain. (Paid after you're licensed, not upfront.)
  • Already licensed in FL/TX/GA? You can start right away
  • A reliable computer and a wired Ethernet connection

Heads up — Open Enrollment is an intense, fixed sprint: November 1 through January 15 is 50 hours across 6 days, with no vacation during the window. Eleven weeks, all in.

Ready? Apply now — the earlier you're set up, the sooner you start earning.

Base pay of $24/hour is guaranteed for hours worked. Overtime is paid at $36/hour where state law provides for it; overtime rules and thresholds vary by state. Commission, bonus, and total season figures are illustrative, based on individual performance, and not guaranteed.

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