Preparing for Open Enrollment Season

by Stephanie DePaco, Vice President of HR Services

October marks the unofficial start of Open Enrollment Season. This is a critical time for HR teams, business owners, and employees alike. Between plan renewals, benefit updates, compliance considerations, and communication logistics, the decisions made over the next several weeks will impact employee satisfaction and financial outcomes well into 2026.

At Payentry’s Insurance Services Division, we help companies navigate this period with confidence, clarity, and compliance. Whether you’re offering benefits for the first time or preparing for your renewal cycle, the key to a smooth and successful enrollment is early preparation and expert support.

Here’s how to get ready for Open Enrollment in 2025 and how our Payentry Insurance Services team can help.

Step 1: Start with a Strategic Review

Before you finalize any offerings, take time to evaluate your current benefits package:

• Are your plans still cost-effective for you and your employees?
• Are you offering benefits that reflect today’s workforce expectations such as mental health, voluntary benefits and telehealth?
• Have you received employee feedback that indicates confusion or dissatisfaction?

Our Insurance Advisors can provide comparative plan analysis, benchmarking data, and custom recommendations to align your benefits with your budget, company culture and workforce size.

Step 2: Know What’s New for 2026

Every year brings regulatory updates and market shifts. In 2025, employers should pay special attention to:

• Plan affordability thresholds under the ACA.
• New carrier options or network changes in your region.
• Evolving benefits trends.

Our team stays on top of all major compliance updates and carrier policy changes, so you don’t have to. We help you understand what’s changing and what that means for your workforce.

Step 3: Communicate Early and Often

One of the biggest frustrations employees face during open enrollment is a lack of clear, timely information.

We recommend:

• Hosting virtual benefits meetings.
• Providing easy-to-read plan summaries.
• Offering one-on-one Q&A opportunities with our benefits advisors.
• Sharing updates across multiple channels including email, employee portal and printed flyers.

The earlier you begin, the more confident and compliant your enrollment process will be. Doing so also contributes to greater employee satisfaction, retention, recruitment and an overall boost for company engagement.

Step 4: Streamline the Process

Manual forms, confusing plan documents, and scattered communications can lead to costly errors and delays.

With Payentry, you benefit from:

• Integrated benefits enrollment tools that coordinate perfectly with payroll and HR.
• A guided employee portal that walks users through their options in a clear and concise manner.
• Real-time, responsive and personal support from our team to troubleshoot issues and answer questions.
• Carrier connectivity, so changes flow seamlessly to providers.

Our goal is to make the experience efficient for you and for your employees.

Step 5: Partner with an Expert

Choosing and administering employee benefits is one of the most high-stakes responsibilities employers face. It impacts employee retention, satisfaction, and your bottom line. That’s why having a dedicated benefits partner makes all the difference.

Payentry’s Insurance Services Division offers:

• Licensed benefits advisors.
• Strategic plan design consulting for your ongoing benefits objectives.
• Compliance support (ACA, COBRA, ERISA).
• Enrollment services and employee advocacy.

Whether you need help negotiating renewals, educating your team, or navigating regulatory changes, we’re with you every step of the way.

Let’s Make Open Enrollment Easy

The decisions you make this season can shape your workforce experience for the year ahead. With the right guidance and tools, open enrollment doesn’t have to be overwhelming. It can be an opportunity to showcase your company’s commitment to your people.

Need help getting started?

I invite you to reach out to our Insurance Services division today for a complimentary Open Enrollment Readiness Consultation. We’ll help you review your current offerings, evaluate new options, and execute a smooth, stress-free enrollment.

Need assistance with employer benefits or open enrollment now? Contact us for a complimentary conversation and learn how we can simplify benefits and open enrollment for you at 925.239.8142 and at benadmin@payentry.com. Health/Life licensed in AR AZ CA CO CT FL KS MA MI MO NC NM OH PA TN TX SC VA

Let’s Talk. Our personnel management professionals provide expert support in payroll, workforce management, human resources, benefits administration, and retirement planning services.

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* MPAY LLC dba Payentry (Company), is not a law firm. This article is intended for informational purposes only and should not be relied upon in reaching a conclusion in a particular area of law. Applicability of the legal principles discussed may differ substantially in individual situations. Receipt of this or any other Company materials does not create an attorney-client relationship. The Company is not responsible for any inadvertent errors that may occur in the publishing process.