Over the last year, I’ve worked with Segal Benzers and our clients to understand and apply AI safely and wisely to the HR and benefits communications we create. We’ve learned much and had lots of fun experimenting. (Ask ChatGPT to explain a 401(k) plan in Dr. Seuss’ voice; then ask the AI to talk to you as Dr. Evil and Dr. Dre!)
Joking aside, we’ve seen the ease and efficiency that tools like Copilot, ChatGPT, and Claude bring to standard communication processes. It’s freed up time and headspace for strategic thinking and creative work. And we’ve also been impressed with how generative AI is reshaping user experiences to be simpler, more intuitive, and more user-directed.
As we look to open enrollment, the signs are clear: This isn’t just another same-old-same-old open enrollment. It’s time to reimagine what’s possible in an AI-forward open enrollment.
As you read through these AI-forward best practices, be sure to have your favorite generative AI tool at the ready to try out our recommendations. Note: Be sure not to input any private, confidential, or proprietary data or information into a public AI tool. The Try This prompts below should be used with broad, non-specific information. If you want to try it with specific company or HR-related details, check with your IT department to make sure the AI tool you’re using is company-approved.
A successful open enrollment begins with a clear, detailed communications strategy. Generative AI can give you a jump start on critical strategy elements, like helping you define objectives and calls to action, understanding your target audiences, aligning messages with organizational goals, brainstorming themes and taglines, and summarizing source documents.
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Just like that, AI can help accelerate the strategic planning process, so you can lean on your human communications experts to customize the strategy that fits your situation.
It’s a fact: Personalization increases engagement in benefits. Yet, creating audience-targeted or one-to-one communications has historically required benefits teams to do some heavy lifting. Generative AI has profoundly changed that experience.
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Want to take it to the next level, moving beyond targeted messages to more user-directed personalization? Consider embedding an AI assistant into your benefits or enrollment website or other digital channels. Employees can share basic information about themselves, such as I live in Utah or I’m planning surgery this year to generate tailored content. Think on-the-fly, hyper-personalized plan comparison charts. And if you can bring in HRIS or similar data, the experience just gets better.
Natural language interfaces and real-time, in-flow decision support tools can make choosing benefits easier than ever for your people. We’re seeing leading employers integrating AI assistant-like capabilities within their employee-facing digital channels, like benefits websites, intranets, or Slack. The conversational format allows users to ask for what they want and need in their own words—no benefits expertise required.
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As employees use generative AI tools for their own search questions, they are coming to expect a super-smart benefits assistant by their side. And remember, these same generative AI tools can help HR and benefits teams save time and effort by offering instant responses to employee inquiries, even after hours.
Do you know how your health, insurance, and financial vendors are using AI to engage your employees? How are they deploying AI to support decision-making? Do you know how their AI models are trained and tested? And are you sure they’re providing clear, accurate, consistent information and guidance?
For 2026 open enrollment, it’s extra important to answer these questions. We’re big fans of mapping employee touchpoints during open enrollment communications planning. This will show you how and where employees are getting lost as they navigate your programs. It’ll also help you introduce the best solutions to your employees and show you how to best organize content and integrate resources across vendors and platforms.
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Using AI to research publicly available information about your partners is a great starting point for understanding and testing out the user experience yourself.
Evaluating the effectiveness of communications strategies, messaging, and channels is essential. Are employees opening and clicking? Do they understand coming benefits changes? Do they value your programs? Are they completing calls to action?
AI-powered research platforms like Remesh and conversational AI tools embedded in your benefits websites and other digital channels can help you gauge how your employees feel and can measure results in almost-real-time. You can also see what people are asking about on demand, which means you can offer more proactive communications and support. And AI can provide ideas for improving and refining your tactics to drive results.
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As you measure and track results—and make it easier and faster for yourself with AI tools—you’re building the business case for future communication investments.
By implementing these best practices and embracing the capabilities of AI, organizations can enhance the open enrollment experience, leading to better-informed employees and more effective utilization of benefits.