HR playbook · AI Employee: Harry

Open Enrollment & Benefits Changes

OE completion rate > 95% before deadline

Install this playbookBack to marketplace
The problem

Open enrollment is a six-week fire drill every year. HR mails PDF benefit summaries nobody reads, holds Q&A calls half the company skips, gets 400 identical questions in Slack, chases the last 15% of employees to submit their elections, and reconciles a spreadsheet of exceptions from a vendor with byzantine tiers. Life events (marriage, birth, adoption) between windows compound the chaos — an employee's new baby means a 30-day change window, and missing it costs the family real money.

At a glance
Trigger
Cron (annual window) + form
Approvals
Employee confirmation; HR review for late elections
What it does
Writes to your systems
Systems
Benefits platform · HRIS
How it feels in production

An hour-by-hour walkthrough.

Open enrollment opens Nov 1. Remy takes the roster, per-employee eligibility, and current elections from the HRIS. It personalises the enrollment packet for each employee: - Priya: current elections (medical: PPO family tier, dental: standard family, vision: none, HSA: $2,400/year, life: 1x salary) - Recommended review: dependent-care FSA eligibility (Priya has a new dependent from mid-year birth), commuter benefit (Priya's back in-office post-COVID pattern) - Cost preview per option: current vs. each what-if scenario the employee might consider Every employee gets a Slack DM Nov 1: "Open enrollment is open through Nov 30. Your current elections, personalized recommendations, and one-click access. Ask me anything about your benefits." Through the window, Remy answers questions in Slack DMs — "what's the difference between the PPO and HDHP", "what's the family maximum out-of-pocket", "if I put $3,000 in HSA, what's my paycheck impact" — grounded in the actual plan documents (SPDs, SBCs) and Priya's specific salary and family. Every DM answer is confidential; benefit selections stay private. As the window nears close, Remy nudges anyone who hasn't submitted (day 7 out, day 3 out, day 1 out) with the specific fields they need to complete. On close, elections finalize; Remy syncs to Workday + payroll + carriers, verifies contribution schedules against pay cycles, and files the year's enrollment record. Mid-year life events (marriage, birth, adoption, divorce): Remy detects the HRIS change or receives the employee's DM, opens the qualifying-life-event window, personalises the change form, and shepherds through the 30-day window before it closes.
How it works

Step by step.

  1. 01

    Personalize enrollment packet per employee

    Current elections, cost preview per option, personalized recommendations from life-stage signals (recent marriage, new dependent, commuter pattern change, salary change).

    Workday · Benefits admin · Payroll · Life-event signals
  2. 02

    Launch + educate in-channel

    Slack DM to every eligible employee. Q&A in DM with plan-document-grounded answers. Confidential — benefit selections never leak. Cost-impact calculations use the employee's own salary.

    Slack · Teams · Plan documents (SPDs, SBCs) · Benefits admin
  3. 03

    Graduated nudges before window close

    Day 7, day 3, day 1 nudges for anyone incomplete. Escalation to manager only if 3 days from close and no response. HR sees completion dashboard live.

    Slack · Teams · Enrollment tracker · HR dashboard
  4. 04

    Sync elections + verify pay-cycle alignment

    On close, elections finalize. Sync to Workday, payroll, carriers. Verify contribution schedules align with pay cycles (biweekly, monthly, semi-monthly variations).

    Workday · Payroll · Carrier feeds
  5. 05

    Handle qualifying life events year-round

    Marriage, birth, adoption, divorce, coverage loss: 30-day change window. Remy detects HRIS change or receives employee DM, personalises the change form, executes on submission.

    HRIS · Life-event forms · Slack
Systems and wiring

What you connect to make this run.

Workday · BambooHR · HiBob · Rippling

read+write

HRIS carries eligibility, current elections, and dependent records. Write approved elections + life-event changes. Payroll picks up contribution changes on next cycle.

Benefits admin (Workday Benefits · Sequoia · Rippling · Zenefits)

read+write

Plan documents, tier structures, cost tables. Election submission + carrier notification. Handles the multi-carrier reality most companies have (medical carrier, dental carrier, vision carrier, HSA administrator, FSA administrator).

Slack · Teams

read+write

Personalised DM, Q&A, nudges. Every interaction private per employee — HR never sees the specific questions asked, only aggregate topic patterns.

Plan documents (SPDs · SBCs · certificates)

read

Grounded answers cite the plan document paragraph. No paraphrasing benefit terms. When plan documents are ambiguous, Remy escalates to HR + benefits broker for clarification.

What changes

Before and after, honestly.

Enrollment completion rate by window close
Before
70-85%
After
97%+
HR hours per open enrollment cycle
Before
200-500 hours
After
40-80 hours (only exceptions + policy)
Employee questions escalated to broker
Before
40-60% of questions
After
5-15% (rest self-served with grounded answers)
Missed qualifying-life-event windows
Before
5-15 per year (missed 30-day deadline)
After
Under 1 per year
Related

Playbooks that pair with this one.

HR

Parental Leave Intake

New-baby qualifying event triggers both benefits change + leave intake.

HR

HR Policy & Benefits Q&A

Year-round benefits Q&A uses the same plan-document grounding.

HR

Employee Data Updates

Dependent additions + address changes flow through the same HRIS updates.

Frequently asked

Answers about this playbook.

How does it handle multi-country benefits?

Country-specific plan documents + eligibility rules. Employees in Germany see German benefit options with grounded answers from the German SPD. No cross-jurisdictional confusion.

What about domestic partners + non-traditional families?

Full support for domestic partners, civil unions, and non-traditional dependents per each plan's eligibility. Correct tax treatment applied (some jurisdictions treat domestic-partner premiums as imputed income).

Can employees model complex scenarios (e.g., HSA + FSA together)?

Yes — Remy runs the modeling with the employee's specific salary + tax bracket + coverage tier. Handles the HSA-limits-with-partial-year-coverage nuance that trips up most vendor calculators.

How does it handle late enrollees or missed elections?

Employees who miss the window default per plan rules (usually current elections continue). Late-election requests route to HR for one-off review; exceptions rare per plan rules but Remy drafts the paperwork if approved.

Does it work for smaller companies without a benefits admin platform?

Yes — Remy can operate against a spreadsheet + carrier portals for smaller companies. Ideal setup is a benefits admin platform but not required. Manual carrier notifications handled as write-with-verification.

See it run on your data.

Free plan, no credit card. Connect the systems this playbook needs and run it against a past event first.

Book a demoMore HR playbooks