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

For small businesses, benefits can quickly become overwhelming. As headcount grows, so do the challenges: managing multiple carriers, syncing payroll deductions, tracking eligibility, and keeping up with compliance requirements like ACA and COBRA. Without the right system, HR and finance teams get buried in manual updates, while employees get frustrated with clunky enrollment processes and slow reimbursements.

The right benefits administration platform should unify everything — from carrier connections to payroll sync — into one simple system. It should automate compliance, give employees a modern self-service experience, and provide finance and HR leaders with real-time visibility into costs and enrollment trends.

This guide shows the critical areas small 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

As small businesses grow, they need access to competitive plans while keeping administration simple. Benefits systems should connect directly with carriers to automate enrollments and changes, eliminating manual errors and delays. 

Rippling integrates directly with top carriers and brokers, ensuring employees can access affordable, high-quality plans while HR avoids double-entry.

RFP questions to ask

• Which carriers and brokers do you integrate with directly?

• Do you support automated EDI feeds for enrollments and changes?

• Can you provide small businesses access to enterprise-level plans?

• How quickly are updates reflected in carrier systems and payroll?

2. Payroll sync and deductions

Payroll and benefits have to stay perfectly aligned as employees enroll, change coverage, or experience life events. Errors in deductions can mean compliance violations and upset employees. 

Rippling unifies payroll and benefits in a single system, so deductions and contributions update instantly and automatically across every payroll cycle.

RFP questions to ask

• Do benefits elections flow directly into payroll deductions?

• Can employer contributions be configured by percentage, flat rate, or capped amount?

• How are retroactive coverage changes handled in payroll?

• Do you provide previews of deduction changes before payroll runs?

3. Compliance and eligibility management

With multiple states, employees, and plan types, compliance becomes a growing burden for small businesses. Missing ACA reporting or COBRA notices can result in steep penalties. 

Rippling automates ACA measurement and reporting, manages COBRA notifications, and provides I-9/E-Verify compliance — all tied directly to the employee record for accuracy.

RFP questions to ask

• Do you automate ACA tracking and reporting?

• How do you handle COBRA enrollment and notices?

• Do you support I-9 and E-Verify as part of benefits workflows?

• Can we export compliance reports for audits or regulators?

4. Employee enrollment experience

Employees expect an easy, modern enrollment experience. If benefits are confusing, they’ll turn to HR for support, creating extra work and slowing down enrollment. 

Rippling gives employees a guided, digital experience to compare plans, add dependents, and update coverage from their mobile device or desktop — all in the same app they use for payroll and HR tasks.

RFP questions to ask

• Can employees compare plan costs and coverage before enrolling?

• Do you support mobile-friendly enrollment with e-signatures?

• How are qualifying life events managed in the platform?

• Can employees update dependents and coverage through self-service?

5. Reporting and visibility

Small businesses need clear visibility into benefits costs to manage budgets and make strategic decisions. Reporting should show enrollment trends, employer contributions, and costs by team or department. Rippling provides real-time dashboards and exportable reports so HR and finance leaders always have accurate, up-to-date insights.

RFP questions to ask

• Do you provide dashboards that show benefits costs and enrollment trends?

• Can reporting be segmented by department, location, or role?

• Do you support variance analysis across different open enrollment cycles?

• Can benefits data export into Excel, Google Sheets, or BI tools?

How Rippling helps small businesses

Rippling Benefits Administration is designed to make managing benefits simple and stress-free for small businesses. It connects directly to carriers, syncs deductions automatically into payroll, and enforces compliance by default. Employees get a smooth, mobile-friendly enrollment experience, while HR and finance leaders get dashboards that show costs and enrollment status in real time.

With Rippling, small businesses can:

• Access competitive health, dental, and vision plans through top carriers

• Sync payroll deductions automatically with benefits elections

• Automate ACA, COBRA, and I-9 compliance workflows

• Give employees a guided, self-service enrollment experience

• Report instantly on costs, contributions, and enrollment trends

Rippling RFP for benefits administration software for small businesses example

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