Annual Enrollment

Annual Enrollment is the yearly period when employees review and select their benefits for the upcoming plan year through the Alight Worklife platform.

Project Overview

Alight has redesigned its Annual Enrollment experience to move beyond today’s long, click‑heavy process by simplifying page turns, improving navigation and introducing more personalized, holistic plan recommendations that reduces friction, improves clarity, and addresses common client concerns about speed, usability, and user confidence.

My Role
Lead Product Designer, Led the end‑to‑end design process, managing a team of 3 designers

Team
3 Designers, 2 UX Researchers, and the product health team including 1 Product manager

What We Were Solving

 

Problem

Annual Enrollment was a long, confusing, and one‑size‑fits‑all experience that made it hard for users to understand their options, feel confident in their decisions, and benefit from personalized guidance.

Solution

A streamlined, redesigned Annual Enrollment experience focused on personalized recommendations and a more compact way to present benefits, reducing page turns, cognitive load, and the effort required to make confident decisions.

 

Strategic Highlight

Leadership level framing

Driving Clarity and Alignment at Scale

Defined clear experience direction and decision frameworks, enabling cross‑functional teams to align quickly.

Strengthening Team Through Design Leadership

Leveled up team effectiveness by mentoring designers, fostering a culture of collaboration and ownership

Building Scalable Design Foundations

Created repeatable design workflows that improved alignment across design, product, and engineering

Results at a Glance

10/10

Success rate

Overall end‑to‑end success rate

8.5/10

Confidence

Participants confident about their plan selections

10/10

Personalization

Participants felt packages were personalized to them

8.5/10

Perceived effort

Stepper helped set expectations; no drop‑offs observed

83% ↓

Reducation in pages

Reduced pages in guided flow from 43 to 7

Metrics with context

Where we started

Classic Alight Annual Enrollment flow

The Alight Annual Enrollment flow had remained unchanged for years. This project aimed to modernize the experience by updating the flow to align with Alight’s new design system while improving the experience.

See classic prototype Here

Discovery Process

Research and alignment

Understanding the problem area

To build a clear understanding of the problem space, I guided my designer through a structured discovery phase focused on identifying key pain points in the current experience, as well as uncovering meaningful opportunity areas In parallel, I directed a competitive landscape analysis to assess how similar products approach these challenges and where their solutions succeed or fall short.

Defining the problem

Building on existing research and personas, I led the team in synthesizing key insights to clarify the problem space and set design direction. We surfaced core issues including low user confidence, page turn fatigue, and unpersonalized plan options. To rapidly explore solutions, I facilitated a Crazy 8s workshop with product and design partners, driving alignment around high impact opportunities.

User flow

I partnered with the product team to define a new user flow aligned to our design approach, centered on two core principles. First, we introduced a consolidated Profile page to capture all key information upfront. Second, we designed a bundled plan system that surfaces tailored benefit packages based on the information provided in the Profile, creating a more personalized and efficient decision‑making experience.

Alignment

I drove alignment across product and engineering by defining MVP scope, establishing clear timelines and milestones, and delivering work in agile two week sprints to maintain momentum and shared accountability.

Collaboration

I facilitated twice weekly working sessions with product using Miro and Figma to maintain close alignment throughout a fast paced timeline. These sessions served as regular design touchpoints to review progress, resolve open questions, and ensure shared understanding as we moved through delivery.

Driving insights from Discovery

Navigation

Reduce click fatigue by prioritizing clarity: show a simple roadmap of where the user is and where they’re going.

Let the user drive

Let users control what they see: display grouped items instead of one question per page, so they can choose where to go.

Personalization

Show progress and value: reveal how their answers are used and offer personalized bundles.

Design Iterations

Mid-fi to High-fi

Early design

We partnered with UX Research to validate the Profile and Bundle experiences through unmoderated usability testing, which confirmed strong task completion while revealing key friction points such as confusion around saving progress, skipping/progressing through sections, and overall flow efficiency. Testing of the Bundle experience showed high user confidence and clear understanding of the bundled benefits concept, but also highlighted gaps in how personalization, enrollment actions, and editing options were communicated.

Constraints

The work evolved through multiple iterations from early concepts to final delivery, with several key friction points along the way. Design team reorganization, scope creep and organization partnership with Savvi, whose approach closely aligned with our emerging design direction. This required thoughtful integration of Savvi elements into our experience, balancing partner constraints with our product vision and design system.

Final Design

The final experience positions the Profile as the central hub for all upfront questions, allowing users to control their path while clearly highlighting the most important decision points. Each section provides contextual guidance that explains how inputs contribute to the creation of personalized health packages, reinforcing confidence and transparency throughout the flow.

The Personal Health Packages, formerly the Benefits Bundle, evolved to incorporate select Savvi platform elements while preserving our original concept. The experience enables users to select or edit packages within a single, unified view, reducing friction and eliminating the need to navigate across multiple pages when plans do not meet their needs.

Results

  • 10 out of 10 participants successfully completed the end to end enrollment experience

  • 8.5 out of 10 average confidence rating in selecting a plan

  • 10 out of 10 participants felt the packages were personalized to their needs

View full prototype Here

🔑 Impact & Key Learnings

Impact:

  • Increased confidence in a high‑stakes decision

    Reduced cognitive load in Annual Enrollment, achieving a 100% completion rate and an average 8.5/10 confidence score in plan selection.

  • Simplified a complex, multi‑step flow

    Introduced a Profile‑first hub that centralized upfront questions, improving early orientation and reducing page turn fatigue.

  • Proven personalization through recommendations

    Validated personalized health packages as an effective decision model, with all participants reporting the experience felt tailored to their needs.

  • Renewed client confidence

    By modernizing a previously dated experience, addressing direct client feedback about visual and interaction debt. This redesign helped reposition Annual Enrollment as a modern, competitive product at a time when client confidence was at risk.

Key Learnings:

  • Adaptability is critical in dynamic organizations
    Successfully navigating organizational change requires flexibility in ownership, process, and decision making while maintaining design quality and momentum.

  • Fast pivots keep work relevant
    Being able to quickly adjust direction when priorities or initiatives shift helped keep the work aligned with evolving business and product needs.

  • Clear timelines drive accountability
    Establishing visible design timelines and milestones created shared expectations, improved cross‑functional trust, and kept design accountable to delivery commitments.

  • Early agile alignment reduces downstream friction
    Working in agile from the outset enabled tighter collaboration with development teams, faster feedback loops, and smoother execution through implementation.