How to Choose Health Insurance and 401(k) Software That Attracts Employees

A strong benefits stack is now a hiring advantage. Candidates expect simple enrollment, transparent costs, and meaningful options for health insurance and retirement—delivered through modern software.

The right benefits administration platform should help you set up health insurance and 401(k) plans in a way that feels seamless for employees, integrates cleanly with payroll and HR, and reduces compliance and admin burden.

This guide walks you through how to evaluate platforms for both health and retirement, which features matter most for engagement, and how to validate ROI before you buy. We’ll also show how a unified platform like Deel helps you deliver a great employee experience while automating the busywork behind the scenes.

Understand your employees’ benefits needs

Before you pick any employee benefits platform, validate what your people actually value. A benefits needs assessment is a collaborative process to identify workforce preferences for coverage, cost, and plan features so you can optimize recruiting and retention.

Start with an employee benefits survey and a few short interviews across roles and locations. Use the data to align plan design and software features with workforce preferences and to increase benefits engagement.

Quick steps:

• Define personas: single early-career, families, frequent travelers, remote employees.

• Run a short pulse survey and optional focus groups.

• Prioritize needs and budget tradeoffs, then map them to software capabilities.

Example questions to ask:

• Health: Which plan types fit you (HMO, PPO, HDHP)? How important are mental health, telehealth, dental, and vision? Do you need family or dependent coverage?

• Experience: Do you want a mobile app for enrollment? Help comparing out-of-pocket costs? Access to virtual advisors?

• Retirement: Would auto-enrollment help? What match or vesting schedule feels competitive? Do you want managed portfolios or target-date funds?

See also: 12 Employee Benefits Trends: Understand the Perks of the Future

Research health insurance and 401(k) software options

Benefits administration software is a platform that manages, automates, and tracks employee health and retirement plan enrollments, eligibility, deductions, and ongoing administration. Many tools also provide health plan decision support or 401(k) administration features such as auto-enrollment and contribution tracking.

A quick benefits platform comparison:

See also: 5 Ways to Offer Health Insurance to Remote Workers

Prioritize personalization and employee guidance features

Personalized benefits guidance uses data such as family size, typical healthcare usage, and financial situation to tailor recommendations for each employee. Strong guidance yields higher-quality enrollments and fewer HR escalations.

What to look for:

• Embedded guidance in the flow of enrollment (not a separate microsite).

• Plain-language plan comparisons and out-of-pocket cost projections.

• Retirement nudges such as default deferral rates, auto-enrollment, and auto-escalation.

Ensure seamless integration with existing hr systems

System integration is the seamless connection of benefits software with HR, payroll, and accounting to automate eligibility, payroll deductions, and enrollment updates. A well-integrated employee benefits platform limits manual data entry, reduces errors, and improves reporting.

Why it matters:

• One source of truth for employee data and deductions

• Faster onboarding and qualifying life event processing

• Cleaner audits, analytics, and compliance documentation

Platforms such as Deel keep benefits data in sync with HR records and payroll, so enrollments and changes flow automatically.

Integration checklist:

• HRIS and payroll connectors (which systems, real-time vs. batch)

• Carrier feeds (EDI capabilities, frequency, error handling)

• 401(k) provider sync (contributions, loan repayments, eligibility)

• SSO and identity management

• Data governance (audit trails, role-based access, PII encryption)

• Reporting exports (custom fields, finance integrations)

Verify compliance support and customer service

Benefits compliance support includes automated eligibility tracking, ACA measurement and reporting, ERISA disclosures, SECURE Act alignment for retirement plans, audit logs, and document storage. For multi-state or global teams, this is essential.

What to assess:

• Health: ACA forms, affordability checks, COBRA administration, dependent verification

• Retirement: Enrollment compliance, nondiscrimination testing support, notices, audit-ready logs

• Global: Country-specific requirements, localized documentation, statutory benefits

Customer service matters just as much:

• Channels: live chat, phone, email, knowledge base

• SLAs and hours (especially across time zones)

• Dedicated customer success vs. ticket queues

• Implementation support and admin training

Evaluate cost, scalability, and user experience

Scalability is a platform’s ability to support growth—adding employees, new plan types, or new countries—without major rework. Evaluate whether the software can expand with your headcount and footprint.

User experience to validate:

• HR admin: Intuitive dashboards, configurable eligibility rules, clear carrier and 401(k) feeds

• Employee: Enrollment support, side-by-side plan comparisons, real-time deductions and contribution tracking, accessible language

Cost drivers comparison:

See also: How to Choose the Best PEO for Health Insurance

Test software through demos and free trials

Hands-on testing catches usability gaps before rollout. Book demos, request sandbox access, and simulate real enrollment scenarios with a small pilot group.

How to run an effective trial:

• Identify internal testers: 2–3 HR admins plus 5–10 employees representing different personas and locations.

• Use an evaluation checklist: Plan comparisons, cost calculators, mobile enrollment, payroll sync, carrier/401(k) feeds, reporting, and admin controls.

• Simulate real workflows: New hire enrollment, qualifying life events, open enrollment changes, contribution updates, and payroll deductions.

• Collect candid feedback and time-on-task metrics; ask, “Could you complete this without help?”

See also: How to Select an Employee Benefits Provider in 9 Steps

Centralize local and global benefits with Deel

If you want benefits that attract talent and run themselves, choose a platform that personalizes employee guidance, integrates across HR and payroll, and keeps you compliant wherever you hire.

Deel unifies HR, payroll, immigration, and benefits in one system, so enrollments, deductions, and compliance workflows stay in sync across states and countries. You gain guided onboarding for employees and audit-ready reporting for finance and legal.

With Deel, you can:

• Set up health insurance and 401(k) plans with integrated payroll deductions and eligibility rules
• Offer country-specific benefits alongside optional global coverage
• Provide employees with clear plan comparisons, mobile enrollment, and real-time contribution visibility

See how it works: Explore Deel’s employee benefits software and book a tailored demo with an expert.