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Benefits Enrollment

Benefits enrollment isn’t just a moment, it’s where trust is built and better decisions begin. The organizations that get it right turn that moment into a movement.

Benefits enrollment done right is a defining part of the employee experience. The most effective approaches are built through personalized, year‑round guidance that gives employees the clarity, confidence, and capability to make better decisions at every stage of their lives and careers.

By the numbers

Workforce trends reshaping the benefits enrollment experience. AI, rising costs and changing employee expectations are reshaping benefits enrollment. The reality organizations need to face is technology will continue to evolve, cost pressures will persist and the needs of the workforce will get more diverse

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Benefits Enrollment

Ready to turn enrollment into an always on advantage?

  • Cost pressure

    73% of companies feel more cost pressure today than at any point in the past decade
    73% of companies feel more cost pressure today than at any point in the past decade
  • AI-adoption

    85%+ of organizations plan to use AI for benefits education within three years
    85%+ of organizations plan to use AI for benefits education within three years
  • Disruption

    1 in 3 companies think it is necessary to make disruptive changes to healthcare programs in the next three years
    1 in 3 companies think it is necessary to make disruptive changes to healthcare programs in the next three years
  • Competition for talent

    Competition for talent is the key business issue influencing benefit strategy for over 56% of employers
    Competition for talent is the key business issue influencing benefit strategy for over 56% of employers
Section 530A (Trump) Accounts opened for funding July 5, 2026 — giving families a new way to build tax-advantaged savings for their children. Program rules are still evolving and employee awareness is low. With no natural enrollment moment to anchor it, the window to get ahead of confusion is narrow. For employers, that first communication isn't just an announcement — it's the moment that shapes whether this opportunity lands as a meaningful investment in their people, or gets lost in the noise. We help you make it a moment of clarity: what it is, who's eligible, and exactly what to do next — building confidence, not confusion.

Insight‑led. Outcome‑driven. Always on.

Delivering experiences that deliver impact beyond the enrollment window.

Enrollment insights and strategy

Starts with data to inform the strategy. Before a single communication is drafted, surfaces insights into where employees may be under‑utilizing benefits, where gaps in understanding or coverage exist, and what enrollment needs to accomplish to deliver measurable results.

Benefits enrollment communications

Clear, hyper-personalized communication before, during and after enrollment. Adding understanding not volume, to drive action not just awareness.

AI-enabled tools

Personalize support with AI‑enabled tools including Employee Coach, which can be leveraged as EnrollMate, and Embark Virtual Assistant, reaching employees in over 100 languages to provide on‑demand access to benefits information all year long. Additional capabilities, such as AI‑enabled video creation, can extend reach and understanding across a global workforce.

Always-on engagement

Enrollment outcomes are built year-round. We keep employees connected to their benefits between windows with targeted content, data-driven nudges, and personalized communications that drive action when it matters most.

Listening & measurement

Continuous insight into what’s working and what’s not. Listening tools surface friction points in navigation, benefits, and care access, enabling ongoing optimization so you can adapt every year, not just react.

Article

From annual event to always-on: Why successful benefits enrollments are built in the other 50 weeks

Our approach

Grounded in WTW's High Impact Employee Experience research, every enrollment strategy we build is designed to create the conditions employees need to make confident, informed decisions.

Helping to guide how employers reset expectations, reframe cost, and establish how employees will engage all year long.

Clarity Employees understand what’s changing, why it matters, and what they need to do. No jargon. No ambiguity. A clear signal in a noisy environment.

Confidence Employees feel equipped to make decisions they won’t second-guess, backed by personalized guidance.

Capability Employees can enroll, use, and navigate benefits with ease. The experience meets them where they are so they can act, not just during enrollment, but all year.

Connection Employees feel that their benefits reflect their employer’s genuine commitment to their wellbeing. Benefits become a relationship, not a transaction.

Ready to help employees make informed benefits decisions? Let’s talk.

Client stories

What it looks like in practice