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).
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.
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).
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.
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.
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.
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.
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.
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
Dental & vision one-pager.
2025 AEP/OEP timeline handout.
Branded quote/proposal template (yes, clients judge design).
Carriers release benefit highlights mid-August—merge these into comparison charts.
Use Quotit to run sample quotes so you can talk numbers, not guesses.
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.
Prioritize high-value clients and chronic-condition prospects (they take longer).
Use SMS reminders—open rates beat email 4:1.
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.
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.
Stick to your appointment blocks.
Log every call, store every SOA—compliance first, commission second.
Use email drip-nudge for unresponsive leads.
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.
Medicare window closes Dec 7 (celebrate, rest, then pivot).
ACA deadline for Jan 1 coverage is Dec 15—send last-chance reminders.
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).
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.)
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