Ready for complex open enrollment questions? AI agents can help

• Key Insight: Discover how AI agents can handle complex, personalized open-enrollment queries.
• What's at Stake: Poor communication risks confusion about benefit details and eroded employee trust.
• Forward Look: Prepare for rising healthcare financial literacy driving more nuanced benefits interactions.
  Source: Bullets generated by AI with editorial review

The key to making the open enrollment process more efficient and effective for both employees and benefit leaders may be to hand questions over to AI agents. 

Open enrollment is one of the most important workplace processes, accounting for nearly 40% of labor costs, according to a recent report from AI-backed HR and employee support platform Cascade AI. Ensuring the process meets employees' evolving needs is increasingly critical, and for many organizations, investing in and leveraging AI agents may be a good way to improve support and keep up with workers' more involved queries.

"Before, we saw a lot of really simple questions being asked, like: What's an HSA? What's an FSA? How does the PPO work? How does the HMO work?" says Cascade's CEO, Ana-Maria Constantin. "But now, we've started seeing a lot of more highly personal, highly complex questions that require more time and effort." 

Read more: What 2026 open enrollment reveals about cost pressures ahead

According to Cascade's findings from open enrollment engagement with its AI agent, one in three questions employees asked related to cost, coverage, care access, or plan comparisons — and these weren't quick, easy fixes. Nearly 60% of AI sessions involved four or more exchanges before reaching a resolution. To Constantin and her team, these longer conversations signaled that employees were bringing more complex needs to the table — and they were right.

Employees' questions to Cascade's AI ranged from paycheck confusion and finding ways to reduce health care costs using their benefits, to identifying the right plan for their family's unique financial situation. Others asked how to submit medication receipts for chronic conditions like diabetes or for GLP-1 prescriptions so they would count toward their deductible. Many questions were even more vulnerable: how to navigate benefits after a miscarriage, what to do when a spouse passes away, or how a terminal cancer diagnosis changes enrollment decisions.

"As employees are exposed to more AI agents, their overall healthcare literacy and financial literacy is going higher, and they're using these solutions to navigate more sensitive moments," Constantin says. "This behavior shows there's a clear gap in the current support ecosystem." 

The right AI solution also supports benefit leaders

Historically, HR and benefit leaders have been in charge of overseeing many of these challenging moments or dealing with employee crises, leaving little space for innovation or long-term thinking. AI offers an opportunity to step back and redesign systems with a much longer outlook in mind, Constantin says. The goal is to build a more thoughtful, supportive infrastructure that better serves employees and strengthens the organization as a whole, and while Constantin agrees there is understandable concern about job displacement, she urges leaders to also see the use of AI agents as a driver for new career opportunities.

Read more: What not to do at open enrollment

"The [benefit and HR] management role is probably the most important right now," Constantin says. "They're the ones responsible for selling employees on AI and continuously pushing the boundary of innovation."

As technology continues to proliferate in the workplace and embed itself in different processes, Constantin urges leaders to look at it as something that adds value to their job, not something that takes away from it. 

"AI can create space for human judgment, collaboration and creativity — the things that we come into work every day for," Constatin says. "It creates space for what actually makes us human in the workforce."