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

Evans Scholars

Chicago, IL · On-site +1

$15.50 - $20/hr

We are also open to remote working from anywhere across the US. We have a very comfortable and ... Must be entering Junior or Senior year and enrolled in an engineering, geology, or science-related ...

Law Clerk - Fall Start

Chicago, IL · On-site +1

$21 - $25/hr

Job Requisition ID: 56315 Opening Date: 05/21/2026 Closing Date: 06/25/2026 Agency: Department of ... This is a paid and remote position, not an internship. There is flexibility around the work ...

Law Clerk - Fall Start

Chicago, IL · On-site +1

$21 - $25/hr

Job Requisition ID: 56315 Opening Date: 05/21/2026 Closing Date: 06/25/2026 Agency: Department of ... This is a paid and remote position, not an internship. There is flexibility around the work ...

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Showing results 1-20

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 May 28, 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 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:

High Ticket Sales Consultants-Remote

Pinnacle Way Of Life

Chicago, IL • On-site, Remote

Full-time

Posted 7 days ago


Job description

Overview
Built to grow around real life, not replace it.
A flexible, results-oriented opportunity designed to fit alongside family and existing commitments.
This is a performance-driven opportunity in the personal and professional development space, backed by a global organization with 20+ years of operating history.
You'll have full training from the start, ongoing mentorship, and access to a community of successful leaders worldwide. The model follows a proven three-step framework designed to integrate realistically alongside family life and existing work commitments, so you can build steadily and intentionally.
From there, it's simple: apply the framework, lead quality conversations, and let results reflect your execution.
Clear communication, open-mindedness, and coachability are essential.
This is not traditional employment. If you're looking for a boss and a salary, it won't fit. If you're comfortable taking responsibility for outcomes, it could.
The Work & The Standard
The work is straightforward. The standard is not.
You'll lead structured, one-on-one conversations with individuals who have already expressed interest through modern marketing channels. These are alignment-based discussions, not transactional pitches.
There is no cold outreach, no chasing, and no pressure tactics. The framework is established. Execution is personal.
How the Model Functions
Participants generate income through client enrollment into established, high-value programs using systems, training, and resources provided within our ecosystem.
There is no hourly structure and no artificial ceilings. Results reflect consistency, decision-making, communication, and follow-through.
Who This Tends to Work For
  • Experienced professionals from sales, consulting, recruiting, coaching, or similar client-facing backgrounds
  • People who have performed in results-based environments
  • Those who value autonomy over supervision
  • Growth-minded individuals who take ownership seriously
  • Operators who want effort and outcomes directly connected

Who This Is Not Designed For
  • Anyone seeking traditional employment or guaranteed income
  • Early-stage sales beginners
  • Individuals who require constant direction or external motivation
  • Those uncomfortable with accountability or self-management

Next Step
Apply only if this resonates.
The next page includes a short questionnaire to confirm alignment and expectations. Applicants who appear to be a strong fit will then be invited to a 10-minute alignment call to determine whether it makes sense to continue the conversation.
This process is selective by design and focused on mutual fit.