The Open Enrollment Communication Playbook for HSA and FSA Benefits

Most HSA and FSA under-enrollment is a communication failure, not a plan-design failure. A four-touch sequence — announce, educate, remind, last-call — with per-pay-period framing and visible match math will move elections more than any plan tweak. Here's the playbook.

Why Communication Is the Lever

Employees don't skip pre-tax accounts because the math is bad; they skip them because the math was never shown. "Contribute up to $4,400" reads as a commitment. "$169 per paycheck, and you save about $58 of that in taxes" reads as a decision they can make in thirty seconds.

The proof this works: in a completed open enrollment at a $1B tech company, a focused communication push (paired with a better member experience) moved 64% of elections to the IRS max — up from roughly 20% the year before — and lifted average per-participant commitments 38%, from $4,039 to $5,561. The entire enrollment ran in six days, all-digital. Plan design didn't change; the story did. (More tactics in our guide to increasing HSA participation.)

The Four-Touch Sequence

Touch	Timing	Job
1. Announce	2 weeks before window opens	Dates, what's new this year, one headline number
2. Educate	Window opens	The full case: math, match, examples, how to enroll
3. Remind	Midpoint of window	Nudge non-completers; answer the top 3 questions so far
4. Last call	48 hours before close	Deadline urgency, one-click path to finish

Four touches is the floor, not a ceiling — but each message needs a distinct job. Four copies of the same announcement train people to delete the fifth.

What Goes in Each Message

Per-pay-period framing, always. Translate every annual number into a paycheck number. "$3,400 FSA limit" means nothing; "$131 per paycheck, roughly $39 of which the government covers" is a decision. Show the tax savings math at two or three salary levels so people can find themselves in it.

Make the match visible. If you contribute or match, lead with it — it's free money and your strongest hook. Spell out that the 2026 limits ($4,400 individual / $8,750 family) are combined employer-plus-employee, so employees know how much room the match leaves them. Nothing kills trust like a match employees can't see; pick an administrator that displays it prominently in the member experience.

Real examples over category lists. "Qualified medical expenses" is abstract. "Sarah puts in $200/month and pays for her gym, her therapist, and her contact lenses tax-free" is concrete. If your plan includes wellness eligibility via Letters of Medical Necessity, say so explicitly — gym and supplements are the examples that make people re-read the email.

Address the fear, honestly. For FSAs, name use-it-or-lose-it and explain your carryover (up to $680 in 2026) or grace period — and link a primer on not forfeiting funds. For HSAs, say clearly: the money rolls over forever and it's yours if you leave. These two sentences remove the most common reason people elect $0.

Live Session Plus Async Explainer

Run one live session (30 minutes, recorded) during the window: ten minutes of the case, twenty of Q&A. The Q&A is the point — the questions tell you what your written materials failed to explain, and the recording becomes your async asset.

Pair it with a short written or video explainer that people can consume in under five minutes on their own schedule. Different employees decide differently; cover both modes and don't force either.

New Hires: Enrollment Is Year-Round

Open enrollment gets the attention, but a company with normal turnover enrolls a meaningful share of its workforce through new-hire onboarding. If your onboarding packet buries the HSA/FSA decision on page eleven of a benefits PDF, every cohort of new hires defaults to $0 and stays there until next fall.

Give new hires the same educate-touch content — per-paycheck framing, match math, real examples — inside their first week, when they're already making payroll decisions. This is the cheapest enrollment lift available, because you're reaching people at the exact moment they're deciding.

Measuring It

Track four numbers, year over year:

1. Participation rate — share of eligible employees electing more than $0
2. Average election — per participant, not per eligible employee
3. Share at the IRS max — your best proxy for employees who fully understood the math
4. Time-to-complete — how fast elections come in; a slow first week means touch 2 didn't land

Elections are also a finance story: every incremental pre-tax dollar avoids 7.65% employer FICA, so a communication push that lifts elections can fund itself.

How Hammock Helps

Hammock runs employee education and enrollment sessions as part of the standard offering — live sessions, async explainers, and enrollment communications are included, not an add-on. The member experience shows the employer match prominently and pre-authorizes wellness eligibility at swipe, which gives your touch-2 email genuinely compelling material.

Employers get a dedicated account manager and a shared Slack channel through the enrollment window, so mid-window questions get answered the same day. Launch takes as little as a week, and the case-study enrollment above ran start-to-finish in six days, fully digital.

FAQ

How many open enrollment emails is too many?

Four to six over a two-to-three-week window works if each has a distinct job (announce, educate, remind, last call). It's repetition of the same message that gets tuned out, not frequency.

What single change moves HSA/FSA elections the most?

Per-pay-period framing with the tax savings shown. Annual limits read as commitments; paycheck-level numbers with the tax offset read as obvious decisions.

Should we run a live benefits session or just send materials?

Both. A recorded 30-minute live session surfaces the real questions; the async explainer serves everyone who won't attend. Neither alone covers a full workforce.

How do we keep enrollment strong outside the annual window?

Treat new-hire onboarding as year-round open enrollment: same framing, same math, delivered in week one. HSA elections can generally change any time; FSA elections are locked until the plan year renews absent a qualifying event.

What results can a communication push actually produce?

In one completed enrollment at a $1B tech company, elections at the IRS max went from ~20% to 64% and average commitments rose 38%. Actual results vary with participation and election mix, but communication is consistently the highest-leverage variable.

The Bottom Line

You don't need a richer plan to get richer elections — you need four well-timed messages, paycheck-level math, a visible match, and examples people recognize from their own spending. Add new-hire onboarding so the machine runs year-round, and measure participation, average election, and share-at-max so next year's playbook starts from evidence.

Want enrollment communications run for you, not by you? Talk to our team.