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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 25, 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.

WFH Remote Health Insurance Agents - $24/hr + OT + Comm & bonus

Thrive Health Benefits

Chicago, IL • Remote

$768 - $1.3K/wk

Temporary

Re-posted 3 days ago

Job description

Already a licensed health insurance agent? Our required states are TX, FL, & GA. You don't need all three state licenses to get started — just your resident license to apply. We'll walk you through getting licensed in FL, TX, and GA and reimburse you for it. The pay is $24/hour, with overtime during Open Enrollment, plus commission on every enrollment. This is a seasonal W-2 role (real paycheck, not 1099), 100% remote. Get licensed and papered this summer and you can start as early as September 1 — Open Enrollment itself runs November 1 through January 15.

Licensing — how it works

·               To apply, you'll need at least your active resident (home-state) producer license and E&O insurance.

·               The role requires active producer licenses in FL, TX, and GA (resident or non-resident).

·               Don't have all three states yet? Apply now — pass the interview and you'll get a conditional offer with step-by-step instructions to get licensed.

·               You obtain the additional licenses yourself (that initiative is exactly what we look for) — typically about 7–14 days if you move fast.

·               Once obtained, we reimburse you 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.

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 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

·               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

·               Weekly commission on every enrollment, plus ancillary and referral income

·               A committed agent can earn $28,000+ across the full September–January season (illustrative, performance-based)

What you'll do

·               Work from home, helping inbound callers enroll in affordable ACA health plans

·               No cold calling — we supply the leads (inbound + live transfers)

·               Full training on sales, systems, and compliance

The honest part

This is seasonal, and Open Enrollment — November 1 through January 15 — is an all-in sprint: 50 hours / 6 days a week. Eleven weeks that can change your year — and open the door to a permanent role for top performers. You'll need a reliable computer and a wired Ethernet connection.

Bring your license and your drive — apply today and we'll help you handle the rest.

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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