Navigating Open Enrollment: A Step-by-Step Guide with Pendant

Remember your first hiring experience? Maybe you were fresh out of college, still just figuring out how a credit card worked. Perhaps you were lucky and had learned a bit about workplace benefits ahead of time. Either way, each job's benefits package is vastly different and despite any prior knowledge, it’s easy to feel overwhelmed and confused come time for open enrollment.

Written by
Kayla Czappa
Published on
May 13, 2025
Navigating Open Enrollment: A Step-by-Step Guide with Pendant

Twenty or thirty years ago, open enrollment meant digging through dense packets full of HR jargon and acronyms like TRACS, HSA, FSA, PPO, and HMO—each sounding more like a secret code than a real benefit. Today, while the tech is more modern, many HR teams are still stuck using outdated processes, leaving employees just as confused and overwhelmed. The only difference? Now the forms, deadlines, and benefit notifications arrive digitally—through Slack, email, and electronic signatures.

How Pendant Helps

Let’s be honest: nobody should have to phone a parent, reference an overgeneralized search engine, or cross their fingers just to pick a health plan.

With the rise of new AI solutions and communication tools, employees don’t just want clear communication during onboarding or open enrollment—they expect it. Just like they want personalization, real-time answers (not a day or two later). Their benefits should feel like what they are—an actual perk, not a puzzle. Discover how to leverage Pendant’s top features to enhance benefits communication across your organization:

Step 1: Prep Your Benefits Wiki

Before enrollment begins, make sure your Pendant Benefits Wiki is fully updated with any new benefit information.The Wiki is searchable and mobile-friendly, it becomes your team’s first line of defense against repeated questions.

Step 2: Make Use of the Pendant AI Assistant

Use Pendant’s AI Assistant to help employees get real-time, personalized answers 24/7—reducing your inbox load and ensuring that every one of your employees feels heard. 

Step 3: Launch Pendant Checklists

Share Checklists that walk employees through open enrollment step-by-step. You can include to-do items like comparing plans, reviewing dependents, confirming elections, and submitting forms—so nothing gets missed and the process feels manageable.

Step 4: Communicate Early and Often

Use Pendant’s announcement feature to communicate benefit changes early and avoid the dreaded post-change chaos of frantic employee questions and concerns. This feature is available 24/7 but is also the first prompt available when updates are made to your benefits wiki portal. These announcements can point employees to newly added Wiki pages (explaining the change), a new-formed checklist, and/or the AI Assistant for additional questions. It also helps to remind employees they don’t need to memorize every benefit or update—they just need to know where to go when questions come up.

Step 5: Monitor Engagement and Feedback

Once open enrollment is underway, use Pendant surveys and/or analytics to gather direct feedback, so you can adjust communications or highlight underutilized perks in real time.

Step 6: Use What You Learn

Pull everything together into one cohesive improvement plan. Identify the benefits that employees struggle to understand—or those they don’t use at all—and use this insight to drive informed changes.

Ready to simplify open enrollment at your company? Learn more about Pendant or schedule a demo today.

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