| 8Weeks before enrollment to start preparing | 3×More utilization with active benefits communication | $0TSB individual cost barrier to entry | 1App download activates all six services |
Open enrollment season arrives every year with an uncomfortable consistency. For large employers with dedicated HR departments, it is a managed process. For the majority of nonprofits — where the person managing open enrollment is also managing a program caseload, grant reports, and a board meeting — it is a scramble that often produces suboptimal outcomes. The consequences are real: employees miss the enrollment window, workers who do not understand their benefits do not use them, and staff who feel their employer does not invest in their wellbeing make career decisions accordingly.
Pre-Enrollment Checklist — Eight Weeks Out
| Done | Pre-Enrollment Action | Why It Matters |
|---|---|---|
| ☐ | Survey staff on benefits satisfaction and gaps — a 5-question anonymous survey takes 15 minutes | You cannot improve what you do not measure. Satisfaction surveys reveal which benefits are valued, which are unused, and what employees wish they had. |
| ☐ | Review prior year utilization data — request reports showing how many employees used each benefit | Low utilization data identifies either communication failures or benefits that are not matching employee needs. |
| ☐ | Audit benefits equity — identify which employee categories (part-time, seasonal) are ineligible for current benefits | Benefits that only cover full-time employees leave a significant share of many nonprofit workforces without support. |
| ☐ | Evaluate whether telemedicine is included, actively offered, or absent — check utilization reflects availability | Telemedicine is the highest-value addition for organizations without comprehensive coverage. |
| ☐ | Confirm compliance status — verify ERISA, ACA, and mental health parity reporting requirements are current | Benefits compliance failures create organizational liability far exceeding the cost of the benefits themselves. |
| ☐ | Set a communication calendar — plan at least three touchpoints: announcement, deadline reminder, post-enrollment activation | One announcement produces low enrollment and lower utilization. Three or more touchpoints produce significantly better outcomes. |
| ☐ | Prepare plain-language benefit summaries — rewrite carrier summaries in plain English | Employees who do not understand their benefits do not use them. Complexity is a utilization barrier. |
| ☐ | Designate a benefits point of contact and communicate their name clearly to all staff | Employees who have questions often do not ask because they do not know who to ask. |
The Communication Checklist — During Enrollment
Effective enrollment communication has five characteristics:
- Specific — tells employees exactly what each benefit covers, not just that it exists
- Repeated — at least three touchpoints during the enrollment window
- Multi-channel — email, team meetings, and posted summaries
- Action-oriented — ‘Here is what to do by [date]’ is more effective than ‘Enrollment is open’
- Inclusive — reaches part-time, seasonal, and remote employees who may not be in building for team meetings
The Post-Enrollment Activation Checklist — The Step Most Organizations Skip
Enrollment is not activation. An employee who has technically enrolled but has never set up their account has not received the benefit.
- Confirm every enrolled employee has received access credentials and knows how to log in
- For telemedicine, host a 10-minute ‘app walkthrough’ at the first team meeting after enrollment
- Send a ‘Your benefits are now active’ message that includes one specific use case
- Add a benefits reminder to 90-day and 6-month check-in agendas for new employees
- Schedule a mid-year benefits check-in email for all staff
Addressing the Part-Time and Seasonal Worker Gap
For many nonprofits, open enrollment exposes an uncomfortable reality: a significant portion of the workforce is ineligible for the primary benefits package. Practical approaches include:
- Make individual-plan telemedicine available to all staff — at under $20/month, individual enrollment is accessible without employer contribution
- Consider a partial subsidy for part-time workers — even $10/month communicates organizational investment
- Communicate the individual sign-up path explicitly for workers not covered by the group plan
- Track part-time and seasonal worker tenure separately — organizations extending even minimal benefits access often see meaningfully better retention
Third Sector Benefits — The Open Enrollment Addition That Pays for Itself
Third Sector Benefits fits into any nonprofit’s open enrollment strategy with minimal administrative burden. For organizations adding it to an existing package, the enrollment process is a single conversation with our team — no carrier forms, no participation minimums, no open enrollment window requirements.
We also provide employer communication templates, plain-language benefit summaries, and an app walkthrough guide you can use in your team meeting — so the activation work is done before you begin.
Make this the open enrollment season that actually changes something. Visit thirdsectorbenefits.com or contact Eric Snyder at eric@thirdsectorbenefits.com.
