Remote September Start Jobs in Chicago, IL (NOW HIRING)

$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)

Two ways to earn before Open Enrollment even starts

• $1,000 bonus for finishing early. Complete all four of these before September 1 and you lock in a $1,000 bonus: (1) transfer your appointments to us, if you currently hold appointments elsewhere; (2) complete your FFM certification; (3) complete your Georgia certification; and (4) complete all of your appointment paperwork requests. Finish your setup in the summer and you can be on the floor September 1 — with $1,000 already earned.

• $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, including Thanksgiving week, 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.