5 prompts to save time during open enrollment with Rippling AI

Open enrollment comes with two workloads, not one. There’s the backend: configuring plans, reconciling billing, pulling multi-location reports. And then there’s the inbox: the same five employee questions, on repeat, for weeks.

Most HR teams absorb both at the same time. The ones moving faster are using AI to offload the repeatable parts.

This guide gives HR leaders, benefits admins, and CEOs five copy-paste prompts built specifically for Rippling AI, covering the full arc of open enrollment from pre-season prep to employee self-service.

What’s inside:

• Prompt 1: An OE readiness check that assesses where you are in the process and generates a sequenced preparation timeline before your carrier rates arrive

• Prompt 2: A multi-location benefits report prompt that pulls employer contributions by employee, location, benefit type, and month in a single query

• Prompt 3: A billing discrepancy diagnostic that traces a mysterious charge back to the specific employee or life event that triggered it

• Prompt 4: An employee-facing plan comparison prompt that surfaces all available medical options, premiums, employer contributions, and HSA eligibility in one view

• Prompt 5: A QLE self-service prompt for employees navigating dependent enrollment, with step-by-step guidance built in

• Guidance on which prompts to run in sequence (1-3) vs. which to share directly with employees (4-5)