The Person Who Used to Stand Next to the Door

Open enrollment season at a large institution is a strange kind of deadline. For two or three weeks each November, tens of thousands of employees make decisions that will govern their healthcare, their tax-advantaged savings, and, in the case of beneficiary designations, the distribution of their assets after death. The portal that accepts these decisions validates field completeness and plan eligibility. It confirms that a selection was made. It does not confirm that the selection was understood.

For most of the history of employer-sponsored benefits, a human being sat between the employee and the form. The benefits enrollment specialist processed paperwork, sure, but the real work was translation. They knew that the high-deductible plan's lower premium looked attractive on screen but could mean thousands in out-of-pocket costs for someone managing a chronic condition. They knew that the dependent care FSA and the health FSA were different accounts with different eligible expenses, and that confusing them meant contributing money you couldn't use for its intended purpose. Money you'd forfeit at year's end.¹ They knew, most critically, that the election being submitted was irrevocable for twelve months under Section 125 of the Internal Revenue Code, and that the confirmation page was a legal commitment, not a receipt.²

As enrollment moved to self-service portals, that translational layer compressed and, in many organizations, vanished. The errors didn't vanish with it. They just became invisible until someone filed a claim.

We spoke with Dee Revocato, a benefits enrollment specialist with twenty-two years at a large state university system, about what she sees that the portal can't show. A note on Dee: she's a composite, a constructed voice drawn from documented occupational knowledge, regulatory realities, and the kind of institutional memory that accumulates over two decades of open enrollment seasons. Her last name is, regrettably, not subtle.

You've been doing this for over two decades. What does the job actually involve that people might not expect?

Dee: People think I'm a data-entry person. Like my whole function is making sure the form gets filled out. And sure, that's part of it. But here's what actually happens. An employee sits down with me during open enrollment and says, "I want the cheap one." That's it. That's their entire decision framework. The cheap one. My job is to figure out whether "the cheap one" is going to cost them four thousand dollars in March when their kid needs an ER visit and they haven't met their deductible.

The form doesn't ask that question. The form asks which plan. I ask why which plan. Those are very different conversations.

What happens when someone makes a mistake on enrollment?

Dee: Short answer? Usually nothing. For twelve months.

And then?

Dee: Then everything at once. Most people have no idea their election is irrevocable. I mean legally irrevocable. Not "call HR and ask nicely" irrevocable. Under Section 125, once the plan year starts, you're locked in unless you have a qualifying life event. Marriage, divorce, new baby, that kind of thing.³ The portal doesn't explain this. It says "confirm your selections." Confirm. Like you're confirming a dinner reservation. You're not. You're entering a binding commitment for a calendar year.

And even when there's an obvious mistake, someone clicked the wrong FSA type, put money into dependent care when they meant health care, correction is a nightmare. The IRS standard is "clear and convincing evidence" that it was a genuine mistake.⁴ And if your employer lets you fix it, they've now created a precedent. They have to offer the same correction to every employee in a similar situation. So most employers just... don't. They can't afford the administrative exposure.

You mentioned FSA confusion. How common is that?

Dee: More common than anyone wants to admit. A health FSA covers medical expenses. A dependent care FSA covers childcare so you can work. They sound similar if you're not paying close attention, and during open enrollment, nobody is paying close attention. They're thinking about Thanksgiving.

So someone enrolls in the dependent care FSA thinking it'll cover their prescriptions. February rolls around, they find out it won't, and the money they contributed? Use it or lose it.⁵ Gone. Just gone.

There's one narrow exception. If you enrolled in the dependent care FSA and you literally have no qualifying dependents, the IRS might let you unwind it, because it's provably impossible for you to benefit from the account.⁶ But if you just picked the wrong one? If you understood the words "flexible spending account" and stopped reading? No fix. You ride it out.

What about beneficiary designations? Those seem straightforward.

Dee: (laughs) Oh, they seem straightforward. That's exactly the problem. The form asks for a name and a relationship. Maybe a Social Security number. Takes thirty seconds to fill out. People do it on their first day of work, between signing their W-4 and figuring out where the bathroom is.

That seems like something the form should communicate.

Dee: The form should communicate a lot of things. It should say, "This document has legal priority over your estate plan." It should say, "If you name your minor children directly, the insurance company cannot pay them without a court-appointed guardian, which will cost your family thousands of dollars and months of delay."⁸ It should say, "Please use legal names, not nicknames, and specify percentages if you're naming multiple people, because 'my children' without names means a legal fight."⁹

But it doesn't say any of that. It's a name field and a dropdown. And people fill it out like it's a name field and a dropdown. The form teaches you how seriously to take it by how seriously it takes itself.

What changed when enrollment went mostly self-service?

Dee: The conversation disappeared.

I used to sit with every employee. Twenty minutes, sometimes thirty. I'd ask about their family situation, whether they were expecting any medical procedures, whether their spouse had coverage elsewhere. Not because I'm nosy. Because the right answer depends on things the form never asks about.

Now they log into the portal at midnight, click through five screens, and hit submit. The portal validates that they picked a real plan. It doesn't validate that they picked the right plan. And those two things are so far apart it's almost funny, except it isn't.

And the errors that you used to catch?

Dee: They show up six months later as claim denials. Or twelve months later when someone dies and the beneficiary designation is wrong. Or in April when someone realizes their FSA money is about to evaporate.

I sometimes think about it like this. The portal is a very good door. It opens smoothly, it closes cleanly, it logs that you walked through it. But it has no idea what's on the other side. I'm the person who used to stand next to the door and say, "Hey, are you sure you want to go through that one?"

Do you think the portal could ever replace what you do?

Dee: It could do more than it does. It could flag that someone with three dependents is choosing a single-coverage plan. It could surface the irrevocability language in something bigger than eight-point font. It could require a beneficiary review every year instead of letting a fifteen-year-old form sit there quietly accumulating legal authority.

But replace the conversation? No. Because the conversation is where someone says, "Actually, my wife and I are separating," and I realize their entire enrollment needs to change. The form doesn't have a field for that. The form has fields for what the institution already decided to ask about. The stuff that actually matters is usually in the margins, in the things people volunteer when they trust the person sitting across from them.

Sixty-five percent of denied claims are never resubmitted.¹⁰ That statistic sits at the end of a chain that often begins during a two-week window in November, with a confirmation page that looked like a receipt.

Footnotes

1. IRS regulations require that health FSA and dependent care FSA contributions cannot be redirected between accounts midyear. See Newfront, "Addressing Employee Health Plan Exception Requests: Part VII," October 2022. https://www.newfront.com/blog/addressing-employee-health-plan-exception-requests-part-vii ↩

2. Section 125 of the Internal Revenue Code requires that cafeteria plan elections be irrevocable for the plan year. See IMA Financial Group, "Open Enrollment FAQs," January 2026. https://imacorp.com/insights/compliance-open-enrollment-faqs ↩

3. TIG Advisors, "Handling Errors Made During Open Enrollment," December 2022. https://tigadvisors.com/handling-errors-made-during-open-enrollment/ ↩

4. The "clear and convincing evidence" standard for correcting mistaken elections under Section 125 is discussed in Newfront, "Addressing Employee Health Plan Exception Requests: Part VII," October 2022. https://www.newfront.com/blog/addressing-employee-health-plan-exception-requests-part-vii ↩

5. SHRM, "FSA Use-It-or-Lose-It Rule Modified," December 2023. https://www.shrm.org/topics-tools/news/benefits-compensation/fsa-use-lose-rule-modified ↩

6. Newfront, "Mistaken Enrollment in the Dependent Care FSA," June 2017. https://www.newfront.com/blog/mistaken-enrollment-dependent-care-fsa-2 ↩

7. Chesapeake Financial Planning, "Beneficiary designation mistakes to avoid," July 2026. https://chesapeakefp.com/beneficiary-designation-mistakes-to-avoid/ ↩

8. Diversified Quotes, "Beneficiary Designation Mistakes," May 2026. https://www.diversifiedquotes.com/beneficiary-designation-mistakes/ ↩

9. WAEPA, "5 Common Life Insurance Beneficiary Mistakes — And How to Avoid Them," March 2026. https://www.waepa.org/resources/5-common-life-insurance-beneficiary-mistakes-and-how-to-avoid-them/ ↩

10. USPTO patent application citing claims resubmission statistics. https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/12277606 ↩