Open Enrollment Playbook.
A 90-day plan for benefits teams entering OE 2026 — whether you're staying with your current HSA partner or migrating.
The 90-day plan
Open enrollment is won or lost in the 90 days before it opens. This playbook lays out the week-by-week plan benefits teams can run to land OE 2026 cleanly — whether you're staying with your current HSA partner or migrating.
Weeks 1–4 — Decide and scope
Week 1. Define the OE objective. Member adoption? FSA-forfeiture reduction? HSA investing penetration? Pick one and write it down.
Week 2. Audit your current stack. App store rating today. Implementation date last year. Average support response time.
Week 3. Score your incumbent and two alternatives on the same five questions (see our Buyer's Guide).
Week 4. Decide. If switching, sign by end of month to leave time for a clean implementation.
Weeks 5–8 — Implement
Week 5. Kickoff. Single implementation lead from your benefits partner. Date in writing.
Week 6. Eligibility file or HRIS connector wired up. Test census uploaded.
Week 7. Card art approved. Member communication template approved.
Week 8. Production cutover scheduled. Admin team trained.
Weeks 9–12 — Comm and convert
Week 9. First member-facing comm. Lead with what changes (the app, the card, the investing tile).
Week 10. Manager toolkits sent to people leaders. 1-page member FAQ.
Week 11. Live OE sessions. Record one for async viewing.
Week 12. OE opens. Daily enrollment dashboard. Day-of support staffed.
OE 2026 checklist
- OE objective defined and shared with leadership.
- Incumbent and alternatives scored.
- Decision made by week 4.
- Implementation kicked off by week 5.
- Member comm template approved by week 7.
- Manager toolkits sent by week 10.
- Live OE sessions held by week 11.
- Daily enrollment dashboard live week 12.
Ready to see it live?
A real demo of the admin portal, the member app, and the integration story — built around your stack.