Must-have benefits administration software RFP template for enterprises in 2025

For enterprises, benefits administration is high stakes. With thousands of employees across multiple entities, states, and even countries, a single error in payroll deductions, ACA tracking, or COBRA notifications can result in massive penalties or reputational risk. Legacy systems and broker spreadsheets can’t scale to meet enterprise needs — leaving HR buried in manual work and employees frustrated during open enrollment.

The right benefits administration software should centralize benefits across entities, connect directly to carriers, sync automatically with payroll and HR, and enforce compliance globally. It should provide a consumer-grade enrollment experience for employees and deliver finance leaders with real-time visibility into costs, contributions, and participation.

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

1. Carrier connectivity and plan options

Enterprises typically manage multiple carriers and brokers across different geographies. The system should connect directly with them all, automate enrollments, and support a wide range of plan types. 

Rippling integrates with major carriers and brokers, handling medical, dental, vision, life, disability, and voluntary benefits across entities — with automated EDI and API connections to keep everything in sync.

RFP questions to ask

• Which carriers and brokers do you support across entities and geographies?

• Do you provide automated EDI and API integrations for all plan updates?

• Can you manage multiple plan types and voluntary benefits in one system?

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

2. Payroll sync and deductions

Payroll deductions are complex at enterprise scale, with multiple contribution models, pay groups, and entities to manage. Any mistake can create payroll errors across thousands of employees. 

Rippling unifies payroll and benefits in one system, automatically syncing elections and life-event changes across all payroll groups, while supporting multiple contribution models and retroactive adjustments.

RFP questions to ask

• Do you sync benefits elections and deductions across multiple payroll groups?

• Can you support complex contribution models across entities (percentages, flat, capped)?

• How are retroactive payroll adjustments handled at scale?

• Do you provide pre-submit previews of deductions for each entity or group?

3. Compliance and eligibility management

Enterprises face overlapping compliance obligations: ACA, COBRA, HIPAA in the U.S., and GDPR and local rules abroad. Benefits systems should automate compliance tracking and reporting globally, enforce eligibility rules, and generate audit-ready records across entities. 

Rippling automates ACA and COBRA compliance, enforces HIPAA protections, and supports GDPR requirements with real-time alerts and exportable audit logs.

RFP questions to ask

• How do you automate ACA, COBRA, and HIPAA compliance across entities?

• Do you support GDPR and local compliance frameworks for global teams?

• Can eligibility tracking adapt by entity, state, or region?

• Do you provide immutable, exportable audit logs for regulators and auditors?

4. Employee enrollment experience

Employees expect a consumer-grade experience for benefits. At enterprise scale, clunky enrollment portals lead to HR backlogs and missed deadlines. A best-in-class system should guide employees through enrollment, provide mobile access, and allow them to manage dependents and life events themselves. 

Rippling delivers a modern, mobile-first experience where employees can compare plans, enroll digitally, and manage dependents in self-service — integrated with the same platform they use for payroll and HR.

RFP questions to ask

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

• Do you support multi-language, mobile-first enrollment experiences?

• How are global life events managed (marriage, relocation, dependents)?

• Can employees manage dependents and elections across multiple entities?

5. Reporting and visibility

Finance leaders at enterprises need visibility into costs across thousands of employees, multiple entities, and jurisdictions. Dashboards should provide real-time views into participation and costs, with drill-down capabilities and variance analysis across regions and time periods. 

Rippling provides consolidated dashboards with segmentation by entity, geography, and department, plus audit-ready exports into ERP and BI systems.

RFP questions to ask

• Do you provide consolidated dashboards across entities, states, and countries?

• Can reports segment data by department, location, or role?

• Do you support variance reporting across open enrollment periods and geographies?

• Can benefits data export into ERP and BI systems for consolidated analysis?

How Rippling helps enterprises

Rippling Benefits Administration is designed to manage benefits at enterprise scale. 

It connects directly to carriers across geographies, syncs payroll deductions instantly, and automates compliance for ACA, COBRA, HIPAA, and GDPR. Employees get a polished, mobile-first enrollment experience, while HR and finance leaders gain dashboards and reporting that consolidate costs and participation across entities and countries.

With Rippling, enterprises can:

• Connect to carriers and brokers globally with automated EDI and API integrations

• Sync payroll deductions across multiple groups, entities, and contribution models

• Automate ACA, COBRA, HIPAA, GDPR, and eligibility compliance

• Give employees a consumer-grade enrollment and life-event experience

• Provide finance and HR leaders with consolidated reporting across entities and geographies

Rippling RFP for benefits administration software for enterprises example

Ready to evaluate vendors?

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