A sample enrollment sprintA US launch: Atlanta and Dallas

Your sprint at a glance

Version: Launch. Open enrollment opens Monday, November 2, so Day 1 is opening day.

The seven days: Mon Nov 2, Tue Nov 3, Wed Nov 4, Thu Nov 5, Fri Nov 6, Mon Nov 9, Tue Nov 10.

Offices:

• Atlanta HQ: about 150 office staff. They're on email and Teams.
• Dallas distribution center: about 400 people, mostly on warehouse shifts, many Spanish speakers, few with work email. You'll reach them through managers and shift huddles, break-room screens, printed guides and texts (only for people who've opted in).

The one message all week: This year is different. See what's new and choose your benefits in Workday by Friday, November 20.

Assumptions:

• The sprint covers the first seven working days (Nov 2 to Nov 10). Your window runs to Nov 20, so a Final push version for Nov 12 to 20 could follow.
• No US public holidays fall between Nov 2 and Nov 10. Veterans Day is Wednesday, Nov 11, the day after the sprint ends.
• All copy is in English. Everything going to Dallas needs a Spanish version (emails, Teams posts, posters, screens, texts, the huddle script and the take-home guide), checked by a native speaker.
• Atlanta times are Eastern and Dallas times are Central. Dallas session times are suggestions, marked "check", because I don't know your shift pattern.
• Your broker runs the Day 3 Q&A. I've also put them at the Day 5 fair (check that they're free).
• You didn't mention an intranet, so I left out the Day 1 intranet banner. The FAQ is shown as "[FAQ link]" wherever you host it (Workday, SharePoint or a Teams tab).
• The standard Launch week doesn't include texts. Because most of Dallas has no work email, I added texts on Days 1, 5 and 7, for people who opted in only.
• Plan names, costs, the deadline time and links are [placeholders]. Nothing about the plans has been made up.
• Emails go out around 10:00 am local time. Days 1, 5 and 6 land on a Monday or Friday because of when your window opens.

The week on one page

Before Day 1

• [ ] By Friday, Oct 23 (this week): book the Day 5 in-person fair for Friday, Nov 6 at both sites. It needs booking at least 14 days ahead.
• [ ] By Wednesday, Oct 21: if you want a Workbliss session at the Day 3 Q&A, book it (14 days ahead of Nov 4).
• [ ] Confirm your broker for the Day 3 Q&A, and for the Day 5 fair if they can come.
• [ ] Brief managers by Thursday, Oct 29: send them the Day 4 note, talking points and huddle script early, especially Dallas shift leads.
• [ ] Build the FAQ page from the starter below and publish it. Have it live on Day 1 if you can, and by Day 3 at the latest.
• [ ] Get everything going to Dallas translated into Spanish and checked by a native speaker.
• [ ] Test Workday login for people without a work email, on a phone and on any shared kiosk or tablet. Put the steps in the FAQ.
• [ ] Set up laptops or tablets at the Dallas fair so people can enroll on the spot.
• [ ] Print posters with QR codes and take-home guides, in English and Spanish. Load the break-room screens.
• [ ] Check the text list is current and includes only people who opted in.
• [ ] Book rooms for the Q&A and the fair, and send Teams invites for the Q&A and the virtual drop-in.
• [ ] Set up a Workday report of enrollment by site, showing totals only.
• [ ] Check every placeholder (see "Check before you send").

Day by day

Day 1: Monday, November 2: It's open

Goal: Everyone knows enrollment is open, the deadline and where to go.

Email (to everyone with email, 10:00 am local)

Subject: Open enrollment is open until Nov 20

Hi everyone,

Open enrollment for [plan year] benefits is now open. You have until [time] on Friday, November 20 to make your choices.

Three things are new this year: - A new HSA-eligible medical plan that comes with a Health Savings Account - A new fertility benefit - Premiums (what comes out of your pay for coverage) are going up by about 6%

One step today: log in to Workday and look at your options. [Workday enrollment link]

We'll explain each change this week, and you can ask our benefits broker anything at a live Q&A on Wednesday, November 4.

Questions? [benefits team contact]

[Sender name]

Teams post

Open enrollment is open until Friday, Nov 20. New this year: an HSA-eligible plan and a fertility benefit, and premiums go up about 6%. Take a look in Workday today: [Workday enrollment link]

Poster and break-room screen

Open enrollment is open. Choose your benefits by Nov 20. [QR code to enrollment link]

Text (opted-in only)

[Company]: Open enrollment is open until Fri Nov 20. New: an HSA plan and a fertility benefit. Enroll in Workday: [short link]

What to watch: enrollments started in Workday, as a total for each site.

Day 2: Tuesday, November 3: What's changed

Goal: People see what's different this year before anything else.

Email (10:00 am local)

Subject: What's new in your benefits this year

Hi everyone,

Here's what's different this year, in plain words.

New: an HSA-eligible medical plan. It has a higher deductible (what you pay for care each year before the plan pays its share): [deductible]. It comes with a Health Savings Account, where you can set aside money from your pay before tax for health costs. [Company contribution, if any]. If you rarely see a doctor, it may be worth a look.

New: a fertility benefit through [provider], covering [what it covers]. If you're planning a family: [link].

Premiums are going up about 6%. Workday shows your cost per paycheck for each plan.

Compare and choose by Friday, November 20: [Workday enrollment link]

Teams post

What's new this year: an HSA-eligible plan with a Health Savings Account, a new fertility benefit, and premiums up about 6%. Plain-words summary: [link]. Choose in Workday by Fri, Nov 20: [Workday enrollment link]

What to watch: clicks through to Workday from today's email and post, as a total.

Day 3: Wednesday, November 4: Ask us anything

Goal: Questions answered live, FAQ published.

The event: live Q&A clinic

• What: a live Q&A on Teams, recorded. [Broker name] answers questions and the benefits team hosts. People can send questions in advance, without their name if they prefer: [form or Teams channel].
• How long: 45 minutes.
• Atlanta: 12:00 to 12:45 pm ET on Teams, with [room] open for anyone who wants to watch together.
• Dallas: 2:00 to 2:45 pm CT (check this against your shift changes), shown on the break-room screen with a Spanish interpreter, [name]. You could also run it as a separate session in Spanish.
• A Workbliss session that fits: Healthcare Financial Planning - USA (virtual). It covers healthcare costs, which suits this year's HSA and premium changes. You could run it before the Q&A or as its own session this week.
• Afterwards: post the recording and the FAQ page by the end of the day.

Teams post

Questions about the new HSA plan, the fertility benefit or your costs? Ask our broker live today, 12:00 pm ET: [Teams link]. Recording and FAQ: [FAQ link]. Deadline Fri, Nov 20.

Dallas break-room screen (added because few people in Dallas see email)

Benefits questions? Ask live today, 2:00 pm, break room. [QR code to enrollment link]

What to watch: Q&A attendance and number of questions asked, per site, plus FAQ page views.

Day 4: Thursday, November 5: Managers

Goal: Managers raise it in team meetings and huddles.

Manager note (email to all managers and shift leads)

Subject: Please talk benefits with your team

Hi [manager name],

This week, please take two minutes in a team meeting or shift huddle to talk about open enrollment. Many of our people, especially in Dallas, won't see our emails, so you're the best way to reach them.

• Use the five talking points below. Shift leads: read the 60-second huddle script at shift start (Spanish version attached).
• Please don't advise anyone on which plan to choose. Point them to Workday, the FAQ and [benefits team contact].
• We'll share site totals as the window goes on, never names.

Deadline: [time], Friday, November 20. [Workday enrollment link]

Thank you, [Sender name]

60-second huddle script (for Dallas shift starts, in English and Spanish)

Quick one before we start. Open enrollment is open now, and it closes Friday, November 20. That's when you choose your health and other benefits for next year.

Three things are new. One: a new HSA-eligible health plan, which comes with a savings account for health costs. Two: a new fertility benefit, for anyone planning a family. Three: premiums, what comes out of your paycheck for coverage, are going up about 6%.

[What happens if you don't enroll.]

To enroll: [how, for example the Workday app on your phone or the kiosk in the break room]. Scan the QR code on the break-room screen or poster.

Need help? Come to the benefits fair tomorrow, Friday, at [time] in the break room. There's help in English and Spanish.

Talk it over at home, then choose by November 20. Thanks, everyone.

What to watch: the number of teams and shifts that held a huddle, as reported by managers.

Day 5: Friday, November 6: Benefits fair

Goal: People get help in person and come to the benefits tables.

The event: in-person benefits fair at both sites

• What: benefits tables staffed by the benefits team and [broker name], with laptops or tablets so people can enroll in Workday on the spot, and printed take-home guides in English and Spanish.
• How long: 2 hours per session.
• Who runs it: the benefits team and [broker name], plus Spanish-speaking helpers in Dallas, [names].
• Atlanta: 11:30 am to 1:30 pm ET, [location].
• Dallas: 6:00 to 8:00 am and 2:00 to 4:00 pm CT in the break room (check these against your shift changes, and add a night-shift slot if you run one).
• Virtual drop-in for anyone working remotely: 30 minutes on Teams at 3:00 pm ET, [Teams link].
• Workbliss sessions that fit: Maximizing Your Employee Benefits Package (onsite) or Employee Benefits: United States (onsite), as a short talk at each site's fair.

Poster and break-room screen

Benefits fair Friday, [time, place]. Enroll by Nov 20. [QR code to enrollment link]

Teams post

Benefits fair today! Atlanta: 11:30 am to 1:30 pm, [location]. Talk to [broker name] and enroll on the spot. Remote? Join at 3:00 pm ET: [Teams link]. Deadline Fri, Nov 20.

Text (opted-in only, Dallas)

[Company]: Benefits fair today in the break room, [times]. Help in English and Spanish, enroll on the spot. Deadline Fri Nov 20: [short link]

What to watch: fair visitors (a tally at each table) and enrollments completed that day, per site.

Day 6: Monday, November 9: Bring it home

Goal: Partners and families can help decide.

Email (10:00 am local)

Subject: Talk your benefits over at home

Hi everyone,

Many of us choose benefits with a partner or family. This one-page guide helps you talk it over at home: [take-home guide link]. Printed copies, in English and Spanish, are at [where].

It covers: - What's new: the HSA-eligible plan, the fertility benefit and the 6% premium rise - How to add a spouse, partner or child in Workday, and what you'll need - Questions to ask each other: how often do we see a doctor? Are we planning a family?

Don't forget what you already have: [EAP name and what it offers], [wellbeing perks], [discounts].

Enroll by Friday, November 20: [Workday enrollment link]

Take-home guide (one page; print for Dallas and hand out at Friday's fair and Monday's shift starts)

Your benefits: talk it over at home - Deadline: [time], Friday, November 20, in Workday. [QR code to enrollment link] - What's new: a new HSA-eligible plan [one-line summary], a new fertility benefit [one-line summary], and premiums up about 6%. - If you do nothing: [what happens]. - Questions to talk through: How often did we see a doctor or fill prescriptions this year? Are we planning a family? Do we want to put money aside for future health costs? Is anyone in the family on another health plan? - Adding a spouse, partner or child: [what you'll need for each person]. - Benefits you already have: [EAP name and phone], [wellbeing perks], [discounts]. - Help: [benefits team contact], help in Spanish: [contact], FAQ: [FAQ link].

What to watch: enrollments completed, per site.

Day 7: Tuesday, November 10: Progress check

Goal: Early enrollers thanked, the rest reminded of the deadline.

Email (10:00 am local)

Subject: Halfway there: enroll by Nov 20

Hi everyone,

Thank you to everyone who has already enrolled. So far, [X]% of Atlanta and [Y]% of Dallas have made their choices.

If you haven't yet, it takes about [time] in Workday: [Workday enrollment link].

If you do nothing: [what happens]. If you want the new HSA-eligible plan or the fertility benefit, [whether you need to choose it].

Missed the Q&A? Watch the recording: [link]. Answers to common questions: [FAQ link]. Still stuck? [benefits team contact].

Deadline: [time], Friday, November 20.

Teams post

Halfway there! [X]% of Atlanta and [Y]% of Dallas have enrolled. Thank you. Not done yet? It takes about [time]: [Workday enrollment link]. Deadline Fri, Nov 20.

Break-room screen (Dallas)

[Y]% of Dallas has enrolled. Your turn: by Nov 20. [QR code to enrollment link]

Text (opted-in only)

[Company]: [Y]% of Dallas has enrolled. Thank you! Not done yet? Enroll in Workday by Fri Nov 20: [short link]

What to watch: the percentage enrolled at each site. Only share a team-level figure where the team is big enough that no one can be picked out.

FAQ starter

1. When is the deadline? [Time and time zone] on Friday, November 20. Enroll in Workday: [Workday enrollment link].

2. What happens if I do nothing? [What happens: whether your current choices carry over, and which benefits need an active choice.]

3. What's changed this year? Three things: a new HSA-eligible medical plan, a new fertility benefit, and premiums going up by about 6%. [Any other changes, such as providers or plan names.]

4. What is an HSA-eligible plan? It's a medical plan with a higher deductible (the amount you pay for care each year before the plan starts paying its share) that lets you use a Health Savings Account (HSA). An HSA is an account where you set aside money from your pay before tax to pay for eligible health costs. [Deductible, premium, any company contribution, and how the HSA is opened.] It can suit people who rarely see a doctor and want to save for future health costs. If you see a doctor often or take regular prescriptions, compare your likely total costs for the year on each plan. Our broker can walk you through it.

5. How much more will I pay? Premiums (the amount taken from your paycheck for coverage) are going up by about 6%. Workday shows your exact cost per paycheck for each plan and coverage level. [Link to cost table, if you publish one.]

6. What does the fertility benefit cover, and how do I use it? [Provider], [what it covers], [who's eligible], [how to get started], [whether it depends on which medical plan you choose].

7. How do I add a spouse, partner or child? In Workday: [steps]. You'll need [information or documents for each person]. [Whether domestic partners are eligible.]

8. I don't have a work email or a computer. How do I enroll? [How to log in to Workday: phone app, kiosk or another way.] You can also get help and enroll on the spot at the benefits fair on Friday, November 6. Break-room posters have a QR code. Help in Spanish: [contact].

9. Can I change my choices after November 20? [Your plan's rules. This is usually only possible after a qualifying life event, such as marriage or a new baby. Broker to confirm.]

10. Where can I get help? [Benefits team contact], the Q&A recording [link], the benefits fair on Friday, November 6, and your manager. Help in Spanish: [contact]. For confidential personal support any time: [EAP name and phone].

Manager talking points

1. Open enrollment runs from November 2 until [time] on Friday, November 20, in Workday. The QR code on the posters and screens takes you there.
2. This year is different: there's a new HSA-eligible plan, a new fertility benefit, and premiums are going up about 6%. It's worth a look even if you're happy with what you have.
3. If you do nothing: [what happens].
4. Help is easy to get: a Q&A with our broker on Wednesday, Nov 4 (recorded), a benefits fair on Friday, Nov 6, the FAQ, and help in Spanish.
5. I can't tell you which plan to pick, but talk it over at home, and if you're stuck, the benefits team or the broker will walk you through it.

Check before you send

Placeholders to fill:

• [Company], [plan year], [Sender name], [manager name]
• [time] and time zone of the Nov 20 deadline
• [Workday enrollment link], [short link] for texts, [QR code to enrollment link]
• [benefits team contact], help in Spanish [contact], [names] of Spanish-speaking helpers and interpreter
• [Broker name]
• HSA plan: [deductible], [Company contribution, if any], how the HSA is opened, premium per paycheck by plan and coverage level, [Link to cost table]
• Fertility benefit: [provider], [what it covers], [who's eligible], [how to get started], whether it depends on the medical plan, [link]
• [What happens if you don't enroll], and [whether you need to choose] the HSA plan or fertility benefit actively
• How to log in to Workday without a work email (app, kiosk) and [time] it takes to enroll
• Adding dependants: [steps], [what you'll need for each person], whether domestic partners are eligible
• Rules for changing choices after Nov 20
• [FAQ link], [form or Teams channel] for questions, [Teams link]s for the Q&A and virtual drop-in, Q&A recording [link], [take-home guide link], [where] printed copies are
• [room], [location], [time, place] on the fair poster, [times] for each site
• [EAP name and phone / what it offers], [wellbeing perks], [discounts]
• [X]% and [Y]% site totals on Day 7
• Any other changes this year

Marked "check":

• Dallas Q&A time, 2:00 pm CT Wed Nov 4: match it to your shift overlap
• Dallas fair times, 6:00 to 8:00 am and 2:00 to 4:00 pm CT Fri Nov 6: match them to your shift changes, and add a night-shift slot if needed
• Broker availability for the fair on Fri Nov 6
• The HSA wording "before tax": have your broker confirm it

Have your benefits team, broker or legal adviser check plan details, deadlines and any required notices before anything goes out. This sprint is a guide, not legal or financial advice.

To run this

The hardest part to do in-house is the in-person moment: getting about 550 people across 2 offices to the benefits table.

Workbliss runs enrollment days that do exactly that, on site at your offices, with a smoothie bar beside your benefits tables, desk and chair yoga and a no-cook nutrition demo:

• Pop-up: one day at one office, for up to 100 people
• Enrollment day: one day at one office, for up to 200 people, adding chair massage and giant board games
• Enrollment week: five days at one office, for up to 300 people
• More offices: the same experiences at every site, with one plan and one invoice

Every option includes an enrollment campaign kit: posters and screens with QR codes, countdown reminders by email and chat, in up to three languages with your logo.

For your benefits talk, Workbliss also runs Employee Benefits: United States.

Book at least 14 days before your fair day: workbliss.ai/benefits-enrollment/ · hello@workbliss.ai

This sample was made in October 2026. Plan details are placeholders, as the sprint says: fill them in, and have your benefits team or broker check them before anything goes out.