Must-have benefits administration software RFP template for midsize businesses in 2025

As companies grow into the midsize stage, benefits management gets exponentially more complicated. What used to be a handful of enrollments can quickly become hundreds across multiple plans, entities, and states. Without the right system, HR and finance teams spend countless hours reconciling payroll deductions, chasing compliance requirements, and manually answering employee questions during open enrollment.

The right benefits administration platform should centralize everything: connect directly with carriers, keep payroll in sync automatically, enforce compliance by default, and give employees a guided, mobile-first enrollment experience. It should also provide finance and HR leaders with dashboards that show costs, participation, and enrollment trends across entities and departments.

This guide shows the critical areas midsize businesses should evaluate in a benefits administration RFP, what best-in-class looks like, and the RFP questions to ask vendors. Plus, we’ll give you a downloadable template so you can start evaluating benefits software ASAP.

1. Carrier connectivity and plan options

Midsize organizations often work with multiple carriers and brokers across different states. Benefits software should integrate with all of them to automate enrollments and eliminate manual entry. 

Rippling connects directly with major carriers and brokers, syncing elections and updates automatically so HR doesn’t spend days reconciling data across systems.

RFP questions to ask

• Which carriers and brokers do you integrate with across multiple states?

• Do you support EDI feeds and API integrations for plan updates?

• Can you manage multiple plan types (medical, dental, vision, voluntary benefits)?

• How do you handle mid-year plan changes across entities?

2. Payroll sync and deductions

At midsize scale, payroll errors multiply if benefits aren’t perfectly synced. Systems must automatically update payroll deductions and employer contributions in real time, with support for multiple contribution models. Rippling unifies benefits with payroll so every change — from open enrollment to a qualifying life event — updates payroll instantly and retroactively when required.

RFP questions to ask

• Do elections and life events update payroll automatically?

• Can you support multiple contribution models (percentages, flat rates, capped amounts)?

• How do you manage retroactive payroll adjustments when coverage changes?

• Do you provide pre-submit previews of deduction changes?

3. Compliance and eligibility management

With multiple entities and states, compliance requirements expand dramatically. Benefits administration software should automate ACA, COBRA, and HIPAA compliance, track eligibility automatically, and provide audit-ready reports. 

Rippling automates measurement periods, notifications, and reporting for ACA and COBRA, while surfacing compliance risks in real time so HR teams can act before issues become penalties.

RFP questions to ask

• How do you automate ACA, COBRA, and HIPAA compliance for midsize businesses?

• Can the platform detect and alert admins to eligibility gaps?

• Do you generate audit-ready compliance reports by entity and state?

• Do you support exporting compliance records for third-party audits or regulators?

4. Employee enrollment experience

At midsize scale, benefits enrollment and life events happen constantly. Employees need a guided experience that reduces confusion and minimizes questions to HR. Rippling gives employees a self-service portal where they can compare plans, enroll digitally, and manage dependents from mobile or desktop — all in the same system they use for payroll and HR tasks.

RFP questions to ask

• Can employees compare plans side by side with projected costs?

• Do you support mobile enrollment and digital forms?

• How are life events like marriage, childbirth, or relocation handled?

• Can employees add dependents and update elections directly through self-service?

5. Reporting and visibility

Midsize finance and HR leaders need detailed reporting to understand participation, contributions, and costs by entity, department, or location. Dashboards should provide variance analysis and export to ERP or BI systems. 

Rippling delivers real-time dashboards for benefits costs, enrollment trends, and employer contributions, giving leaders visibility across the entire organization.

RFP questions to ask

• Do you provide dashboards that show benefits costs and participation by entity or department?

• Can reports be segmented by location, role, or cost center?

• Do you support variance analysis across open enrollment cycles?

• Can data export into ERP systems or BI tools for deeper analysis?

How Rippling helps midsize businesses

Rippling Benefits Administration is built to handle the complexity of midsize companies. It connects directly to carriers across states, syncs payroll deductions in real time, and automates ACA, COBRA, and HIPAA compliance. Employees get a seamless enrollment and life-event experience, while finance and HR leaders get dashboards and reports that track costs and participation across entities and departments.

With Rippling, midsize businesses can:

• Connect to multiple carriers and brokers across states

• Sync benefits and payroll automatically with no manual work

• Automate ACA, COBRA, HIPAA, and eligibility compliance

• Give employees mobile-first, guided enrollment and life-event updates

• Report on benefits costs and enrollment trends by entity, department, or location

Rippling RFP for benefits administration software for midsize businesses example

Ready to evaluate vendors?

This blog is based on information available to Rippling as of October 6, 2025.