Top 5 Common Open Enrollment Challenges for SMBs — And How Your PEO Makes Them Easy to Solve
From selecting and rolling out plan details to answering questions, collecting and processing employee selections, and meeting compliance requirements—open enrollment for employee benefits can be a daunting time of year for small and mid-sized businesses.
The good news? Open enrollment doesn’t have to overwhelm your team or confuse your employees. When you work with a PEO (professional employer organization), you get end-to-end open enrollment support. Your PEO partner handles employee benefits communication, provides direct support to employees, manages compliance, and streamlines the entire process—turning open enrollment into a smoother, more positive experience.
In this article, we’ll explore the five most common challenges SMBs face during open enrollment—and how a PEO can help you successfully navigate the process.
What is employee benefits open enrollment?
Open enrollment is the annual window when employees can enroll in, change, or decline employer-sponsored benefits, including medical, dental, vision, life insurance, disability coverage, and retirement plans. For employers, it’s also the time to introduce new benefits offerings, adjust plan terms, ensure compliance with federal and state regulations, and communicate changes to staff.
Open enrollment represents more than an administrative task for small and mid-sized businesses. It’s your chance to showcase the strength of your benefits program, reinforce confidence in leadership, and position your business as a competitive employer. A well-run enrollment builds employee trust, minimizes compliance risks, and directly contributes to retention and recruitment.
When is open enrollment?
Open enrollment for employee benefits often takes place in the fourth quarter of the year, with coverage beginning January 1. This timing aligns with the majority of employer-sponsored plans and ensures employees start the new year with updated benefits.
However, not all businesses follow this schedule. Some employers hold open enrollment earlier in the fall, mid-year, or in line with their plan renewal cycle. Regardless of timing, the process typically includes:
- Start of enrollment window: Employees can review, select, or change benefits.
- Deadline to elect benefits: Elections must be finalized within the employer’s specified timeframe.
- Coverage effective date: Benefits take effect at the start of the new plan year, typically January 1 but not always.
The Ultimate Guide to Open Enrollment
Download our step-by-step guide to get ahead of open enrollment this year.
Common Open Enrollment Challenges for SMBs
For many companies, employee benefits open enrollment can bring more questions than answers. How do you balance competitive benefits with a limited budget? How do you communicate plan options clearly? And what’s the best way to keep up with compliance requirements?
Here are five of the most common challenges SMBs face during open enrollment—and how a PEO can help you simplify the process, save time, and better support your employees.
Challenge #1 – Communicating Benefits Clearly and Effectively
A successful employee benefits open enrollment starts with clear and consistent communication. Without that foundation, HR teams are often left to translate complex benefits language, respond to repeated questions, and keep employees on track. In some cases, these challenges may even cause employees to miss open enrollment altogether.
With the right support and a strong employee benefits communication strategy, however, the process can be transformed into one that builds understanding, increases participation, and enhances overall employee satisfaction.
That’s where a PEO like G&A Partners comes in. G&A helps you improve communication and guide employees through open enrollment with confidence.
How G&A helps:
- G&A helps you deliver clear, easy-to-understand employee benefits communication across multiple formats, such as email, printed materials, video, virtual meetings, recorded sessions, and more.
- Our benefits specialists assist in hosting live Q&A sessions and providing one-on-one coaching to employees who want deeper clarity.
- We distribute digital benefits booklets and targeted email reminders so every employee gets timely, personalized information.
- We support internal communications planning, including sequencing messages and driving engagement before, during, and after enrollment.
- We can help you build a glossary of benefits terms and FAQs that employees can refer to at any time.
- We provide technology to monitor open enrollment participation, prompting additional outreach to avoid missed enrollment.
G&A Tip: Think like your employees. Replace jargon with clear language, use real-life examples to explain benefits options, and share resources through multiple channels, such as bulletin boards, intranet posts, short videos, or virtual meetings. If you need help with your open enrollment emails, check out G&A’s customizable email templates.
Challenge #2 – Managing Tight Deadlines and Enrollment Logistics
Open enrollment windows are short—often just a couple of weeks—and that compressed timeline leaves little margin for error. HR teams must communicate and distribute plan options, collect elections, process updates, manage confirmations, and finalize compliance requirements while balancing day-to-day responsibilities.
For many small and mid-sized businesses, the logistics of employee benefits open enrollment can quickly become overwhelming, resulting in missed deadlines that can delay coverage or leave employees without benefits. With modern technology and expert support, you can turn that high-pressure window into a streamlined process that reduces errors and keeps employees on track.
How G&A helps:
- Our online enrollment platform simplifies the process, allowing employees to make elections digitally and providing HR with real-time reporting.
- The secure platform integrates with payroll and benefits, reducing manual data entry and minimizing errors.
- As a client, you are paired with a dedicated benefits specialist who manages timelines, oversees progress, and conducts post-enrollment audits to confirm accuracy and reduce compliance risk.
Challenge #3 – Ensuring Compliance with ACA and Other Regulations
Compliance requirements—such as ACA reporting, COBRA notices, and state-specific mandates—can shift from year to year. Every election, communication, and report must meet federal and state standards, and even minor oversights can result in costly penalties or lawsuits. For SMBs without in-house compliance expertise, keeping up with these evolving rules during employee benefits open enrollment can be challenging. But with the right support, compliance doesn’t have to be a stumbling block—it can be a safeguard for your business and employees.
How G&A helps:
- Our plan options include support for ACA reporting, COBRA administration, and other federal requirements on your behalf.
- Our compliance experts stay ahead of regulatory changes and provide proactive updates.
- We provide guidance on benefits-related requirements, minimizing risk during open enrollment and throughout the year.
Challenge #4 – Offering Competitive Benefits on a Small Business Budget
Offering competitive benefits on a small business budget is often one of the biggest hurdles SMBs face. Without the bargaining power of a large workforce, it can feel impossible to secure high-quality, affordable plans with medical, dental, vision, or retirement options.
Still, employees expect robust packages—and businesses that deliver them stand out in today’s competitive labor market. With the right strategy, you can offer benefits packages that rival those of larger employers—positioning your company to attract talent and retain the employees you’ve worked hard to keep.
How G&A helps:
- Through a PEO model, G&A leverages group purchasing power to provide Fortune 500-level benefits at small-business prices.
- We offer a wider range of plan options, helping your business balance affordability with attractive employee benefits.
- Our specialists guide you in designing a benefits package aligned with your goals, employee needs, and budget.
- We provide benefits education support that helps your employees understand and maximize the value of their benefits—increasing satisfaction with your program.
- Our specialists provide benchmarking guidance that compares your benefits against industry standards to help you stay competitive in your market.
- We expand your offering with wellness programs, employee assistance programs, and ancillary benefits that add value without adding significant cost.
Challenge #5 – Supporting Employees with Questions and Enrollment Help
During open enrollment, HR teams often get inundated with questions, ranging from login inquiries and plan comparisons to clarification on complex benefits terminology. For lean HR teams, keeping up with these inquiries can consume valuable time, affect the enrollment process, and delay other priorities. Left unaddressed, this can frustrate employees and lead to missed deadlines. With the right support, open enrollment questions can be managed in a way that reduces stress, empowers employees, and creates a smoother overall process.
How G&A helps:
- G&A offers a dedicated benefits support team and employee helpdesk, giving your employees direct access to expert guidance during employee benefits open enrollment.
- Resources such as our comprehensive benefits booklet or recorded webinars provide 24/7 access to tools that help your employees find answers quickly and independently.
- We handle employee benefits communication and employee inquiries, reducing the internal burden on your staff and improving employee satisfaction.
- Real-time tracking shows HR which employees have questions or need follow-up, ensuring no one falls through the cracks.
How a PEO Turns Open Enrollment into a Strategic Advantage
The right partner can turn employee benefits open enrollment from a source of stress into a streamlined process that supports your employees and your business. With PEO open enrollment support, you not only simplify logistics—you also gain the tools and expertise to reduce administrative pressure, improve communication, and boost engagement and loyalty.
Here’s how it works:
- PEOs, like G&A Partners, act as an extension of your HR team, managing enrollment, compliance, and employee benefits communication—from start to finish.
- Instead of just “getting through” open enrollment, your PEO helps you use this period as an opportunity to boost employee engagement, morale, and retention.
- With G&A’s expertise and technology, open enrollment becomes predictable and efficient, freeing your team to focus on strategic business priorities.
- PEOs go beyond logistics by analyzing employee choices and participation trends, giving you insights to shape future benefits strategies and long-term retention planning.
Frequently Asked Open Enrollment Questions
When should we start planning for open enrollment?
Ideally, 8–12 weeks before enrollment begins. This gives you time to review plan options, prepare communications, and set up technology before launching.
How does a PEO simplify open enrollment?
A PEO like G&A does the majority of the work—researching benefits trends, negotiating plan options, managing communications, hosting employee meetings, answering questions throughout the process, and more.
What makes a successful open enrollment?
Clear communication, accessible tools, timely reminders, and post-enrollment audits are all critical to ensuring employees make informed decisions and elections are processed correctly.
Check out our Open Enrollment Webinar Series for more tips.
What should HR prepare for during open enrollment?
HR teams should clarify goals, survey employee needs, finalize benefits offerings, create a communication plan, and test enrollment systems before launch.
Is ACA compliance part of open enrollment?
Yes. ACA reporting and COBRA administration are integral compliance components during open enrollment. A PEO helps ensure these requirements are met accurately and on time.
