by bswift Insights

Smart Annual Enrollment Strategies to Make Things Easier — and Prove HR’s Value

The annual open enrollment season is high stakes. Employees spend on average just 18 minutes choosing benefits — compared to four hours shopping for a new phone. Yet 81% say benefits influence their job choice. If your enrollment communication for employees misses the mark, the investment you made in your benefits package is wasted and you’ve missed a key opportunity to prove HR’s impact.

Enrollment season shouldn’t wreck your calendar or your credibility. How do you lock down compliance, improve the employee experience, and contain benefits costs — all at once? It starts with the right mix of smart communication, technology, a strong ben admin partner, and smart annual enrollment strategies. If you can strike that balance, you can shift open enrollment from headache to strategic win.

What are the biggest open enrollment challenges for HR?

  • Benefits confusion: 62% of employees say their benefit options feel overwhelming, signaling a disconnect between what’s offered and what’s understood.
  • Sticking with defaults: 89% of employees don’t explore new plans; they stick with what they know, even if a better fit exists.
  • Low employee engagement: 60% of employees aren’t fully using their benefits.
  • Compliance stress for HR: Missed deadlines, unclear comms, or other issues can increase your audit risk.
  • Proving value to leadership: HR works hard, but without measuring impact, the value often feels invisible to the C-suite.
  • Employee participation: Low benefits participation rates make it harder to justify benefit costs and show ROI.

Partnering with a benefits administration expert like bswift can help you address these challenges with actionable insights and tailored solutions.

How can HR improve open enrollment communication?

There are four proven steps to make enrollment easier for employees and less painful for HR, too. And it all starts with having the right strategy in place.

1. Build an annual enrollment strategy like a marketer — set clear, measurable goals

  • Define SMART goals: Be specific. Instead of just saying you want to “increase engagement,” aim for something specific, like “50% more traffic to the benefits site in week one” or “90% of employees show clear understanding of new offerings in post-enrollment surveys.”
  • Segment your audience: New hires, working parents, and near-retirees all have different priorities that need different messages, channels, and timing.
  • Position clearly: Highlight the value of benefits in plain terms employees understand. “Connect with a doctor from home at no extra cost” beats “telemedicine access” every time.
  • Choose the right channels: Meet your employees where they are by communicating with them through the platforms they use most. Use text for field staff, email for desk workers, intranet banners for hybrid employees, and manager toolkits for team huddles.
  • Find a benefits administration partner: Leverage their data-driven insights, tools, and strategies to better segment and engage your workforce.

2. Communicate clearly — ditch jargon, use useful formats

  • Write plainly: Lose the legalese and words like “utilize.” The word “use” exists. Plain language and simple answers help employees make better choices.
  • Avoid walls of text: Mobile-friendly reminders, quick videos, and dashboards with cost comparison visuals, etc. All of these outperform walls of text in PDFs.
  • Use different “content depths”:
    • Bite: “Enroll by Friday!” SMS, intranet banners, and postcards
    • Snack: Explainer videos, benefits summaries, comparison tools, and FAQs
    • Meal: Detailed guides, Q&A webinars, and benefits microsites

3. Use AI in benefits enrollment technology and user experiences to cut friction and guide better choices

  • Streamline setup: AI can scan plan docs, flag errors, and auto-configure options before payroll problems hit. Think of it like a proofreader who never sleeps.
  • Deliver personalized guidance: Real-time recommendations and nudges tailored to usage and risk tolerance.
  • Provide instant support: Conversational tools answer routine questions like “Does this cover orthodontia?” and escalate complex cases to a human.
  • Surface insights: HR can ask bswift’s Emma™, “How many employees haven’t enrolled yet?” and get visual dashboards in seconds.

4. Balance AI and HR tech with the human touch in your annual enrollment strategy

  • Show leadership visibility: Short videos or notes from leaders reinforce that benefits matter to the organization, not just HR.
  • Keep real people in the loop: Chatbots are great for simple questions and quick answers, but when it’s complicated and stakes are high, 75% still prefer human help. Having real people, like the bswift Service Center, means critical situations are handled with empathy and expertise.
  • Create feedback loops: Run post-enrollment surveys or pulse checks to measure confidence and capture pain points, helping you continuously improve the employee experience.

HR experts answer common enrollment questions

Q: How can HR reduce errors during enrollment?
A: Segment employee communications, automate reminders, and use interactive decision tools that flag mistakes before submission.

Q: What’s the best way to explain complex plan options to employees?
A: In addition to interactive decision tools, deploy short, closed-caption explainer videos and side-by-side plan comparison charts. Visuals will always beat a wall of text in a PDF.

Q: How do you balance compliance and employee experience?
A: Use smart content design: surface compliance must-knows in bold, clear language — no more buried footnotes.

Ready to put these annual enrollment strategies to work? Watch the bswift SHRM webinar

Dive deeper with actionable ideas from leading HR experts — watch our on-demand SHRM webinar, “Beyond Checkboxes: Annual Enrollment Strategies That Engage and Deliver.” You’ll get tips and tools to drive results, keep compliant, and maybe even get some sleep back.

Watch the Webinar Now

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