AEP/OEP Preparation Timeline: Month-by-Month Playbook

You know the agents who look calm in October?
They started planning in June—while everyone else was still hunting for sunscreen.

Below is a month-by-month roadmap from now through the end of Open Enrollment. It’s a quick-read version of the detailed timeline, templates, and checklists waiting for you in the free Quotit AEP/OEP Success Toolkit (grab it at the end).

Why a Timeline Blog—and Why Now?

• AEP is only 54 days long. Blink and it’s over.

• OEP follows fast, with ACA enrollment running November 1–January 15 in most states. That means double the prep, double the pressure.

• Major Medicare carrier certifications drop July–September—if you miss them, you miss sales.

• Google Trends shows “AEP preparation timeline” and “Medicare enrollment checklist” spiking in late June—so let’s meet that search intent now.

June: Lay the Groundwork

1. Audit Last Year’s Performance

• Pull your CRM reports: close rate, lapse rate, and average premium.

• Identify which marketing channels actually produced policies (email vs. community events vs. paid leads).

2. Set Sales & Retention Goals

• Goal worksheet tip: Aim for a 15 % bump in cross-sells (dental, vision, hospital indemnity).

• Block time on your calendar for certification modules and content creation.

3. Clean Your Data

• Delete duplicates, update phone numbers, tag clients (turning 65, MA renewals, ACA renewals).

• Pro tip: Use a CRM trigger to flag clients with expiring licenses or missing email addresses.

July: Certify & Re-Engage

1. Knock Out AHIP Early

• AHIP opens in late June. Finishing it before July 15 gives you first-in-line status with carriers.

• Bookmark carrier portals (Humana, Aetna, UnitedHealthcare) and schedule weekly reminders.

2. Start “Warm-Up” Outreach

• Send a casual “We’re gearing up for October” email.

• Post a LinkedIn poll:
  “When do you prefer to review your health plan for the next year?”

  • July/August

  • September

  • October (right at the start of AEP/OEP)

  • I’m not sure — I could use guidance

  💡 This not only boosts engagement, but also identifies clients who are ready to chat now — making follow-up easy and natural.

3. Segment Your Book

• Turning 65, Medicare Advantage renewals, ACA/under-65 clients, and cross-sell prospects all have different needs.

• Load custom email lists for each segment so content resonates.

August: Build Marketing Assets

1. Draft Your Client Emails & Letters

• Welcome-back email (template in the toolkit).

• Appointment-scheduler email with Calendly link.

• Coverage review reminder two weeks before AEP opens.

• OEP-eligible outreach email for clients with qualifying events or ACA plans—remind them you can help year-round

2. Design One-Pagers & Social Posts

• Dental & vision one-pager.

• 2025 AEP/OEP timeline handout.

• Branded quote/proposal template (yes, clients judge design).

3. Preview Plan Updates

• Carriers release benefit highlights mid-August—merge these into comparison charts.

• Use Quotit to run sample quotes so you can talk numbers, not guesses.

September: Final Dress Rehearsal

1. Confirm Compliance

• Call recording in place (CMS requires all marketing & sales calls).

• 48-hour Scope of Appointment rule configured in your e-SOA workflow.

• Check state DOIs for any new marketing regs.

2. Book Appointments

• Prioritize high-value clients and chronic-condition prospects (they take longer).

• Use SMS reminders—open rates beat email 4:1.

3. Run Stress Tests

• Pretend it’s October 15. Can you quote, record the call, capture SOA, and e-sign in <30 minutes?

• If not, troubleshoot now—future you is busy enough.

October: Showtime (But Don’t Panic)

Early October (1–14)

• Medicare marketing officially begins Oct 1—send your “We’re ready!” blast. (Make sure you're adhering to all of the Medicare Marketing guidelines set by CMS.)

• Social countdown graphics: 14 days, 7 days, 1 day.

• Also prepping for OEP? Now’s the time to revisit ACA leads from Q4 last year. Use October to refresh contact lists, update quoting tools, and send a “Let’s chat before Jan 1” email to under-65 clients. Bonus: This also helps catch anyone aging into Medicare soon.

AEP Launch (Oct 15–Dec 7)

• Stick to your appointment blocks.

• Log every call, store every SOA—compliance first, commission second.

• Use email drip-nudge for unresponsive leads.

November: ACA OEP Joins the Party

• Nov 1: Marketplace opens. Dual-licensed agents—switch hats but keep momentum.

• Push dental/vision cross-sell emails (these add revenue without extra certifications).

• For MA clients: remind them of Dec 15 plan effective deadline for Jan 1.

December & Beyond

Mid-December

• Medicare window closes Dec 7 (celebrate, rest, then pivot).

• ACA deadline for Jan 1 coverage is Dec 15—send last-chance reminders.

January–March

• MA Open Enrollment Period (Jan 1–Mar 31) for plan changes—queue automated check-ins.

• Analyze Q4 metrics, survey clients, and start planning 2026 (yes, already).

Why Technology Is Your Secret Weapon

• CRM segmentation & reminders keep you from missing cert deadlines.

• Multi-carrier quoting shows side-by-side comparisons in seconds.

• Call recording + e-SOA inside the same platform = bulletproof compliance.

• Client-driven shopping widget captures leads even when you’re sleeping.

(Spoiler: Quotit does all of the above.)

Ready for the Full Timeline, Templates & Checklists?

This blog is the appetizer; the main course lives in the AEP/OEP Success Toolkit. Inside you’ll get:

• Editable timeline calendar

• Goal worksheets & sales tracker

• Certification checklist

• Email & social templates

• Proposal & quote designs

• Client retention scripts

• And more!!