Help Employees Avoid Open-Enrollment Regret

Written by
Tyler Abbott
Published on
October 16, 2025
Help Employees Avoid Open-Enrollment Regret

I almost always have open enrollment regret. I remember last year, I want to say around November, my co-worker mentioned how great it was to have a DCFSA account.

“A what?” I recall asking him. He went on to explain what a Dependent Care Flexible Spending Account was and how I could’ve been saving money on my childcare expenses. Well, I’ve carried that pain all year long as I’ve paid through the nose for preschool, but no longer! It’s October. Open enrollment season. And now I can contribute to a DCFSA account now that my son is in kindergarten, which is free. D’oh! 

According to a study by Equitable, more than half (53%) of employees regret their benefits selections during open enrollment. The reasons often boil down to two things: a lack of understanding of the options available (19%) and failing to adjust benefits to match lifestyle changes (25%).

Rather than sending employees a mountain of PDFs every October, what if we gave each employee a personal benefits expert? Pendant, and more specifically, the Pendant AI Assistant, can act as a personalized employee benefits guide.

How the Pendant AI Assistant Helps Avoid Open Enrollment Regret

Choosing the right tax-advantaged account—whether its HSA, FSA, or DCFSA—requires some thought, which is why employees often skip them (guilty!). It’s the acronyms that get me. The Pendant AI Assistant simplifies things by translating all the complex tax rules into clear, conversational guidance.

Here’s a few ways the Pendant AI Assistant makes things easier for your employees:

1. Get-To-Know-You Survey

Employees can begin the research process by participating in a survey given by the AI Assistant. The AI Assistant will ask questions about dependents, savings goals, health needs, and more in order to make informed recommendations for benefits selections. 

Likewise, your employees can ask direct questions to the Pendant AI Assistant like: "Can I sign up for both the HSA and the Dependent Care FSA?" The AI Assistant, trained on your company's benefits, provides an accurate, immediate answer, and gives all the finer details, like contribution limits and eligible expenses.

You can also ask the Pendant Assistant to clarify jargon, which is invaluable when dealing with employee benefits. No judgement, either! 

2. Compare Plan Benefits

The Pendant AI Assistant is built to compare health plans instantly.

Instead of reading through paragraph after paragraph of complicated insurance-ese, an employee can ask: "What are the biggest differences between the PPO and the HDHP for someone who is planning a surgery this year?" The AI Assistant will reference all the need-to-know information—premiums, deductibles, and out-of-pocket maximums—and offer actionable advice on what plan to choose.

3. Answers Wherever Your Employees Are

With the Pendant app, that employee benefits guide is available 24/7. No need to wait for an HR follow-up email or spend an evening reading insurance documents. The Pendant AI Assistant is happy to dive into PDFs for you at literally any time of day.

Employees that Use Benefits = Happier Employees

The thesis of Pendant is simple: benefits are only valuable if employees actually use them. The problem is that many employees either don’t know how to effectively use their benefits, or don’t even know that they exist!

Providing a tool like the Pendant AI Assistant gives employees the simple, actionable instructions they need to take full advantage of the benefits you provide. When employees clearly understand and actively utilize their benefits, it leads to increased job satisfaction, reduced HR burden, and an improved return on your investment. 

Don't let your employees become part of the 53% who regret their open enrollment choices! Empower them with Pendant's AI Assistant to make informed benefits decisions every year.

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