2027 Employer Planning Checklist: Key Decisions to Make Now

The decisions organizations make today will shape how prepared they are for 2027.

Employers are heading into the year with several priorities competing for attention — rising healthcare costs, technological change, evolving compliance requirements, and shifting business needs. These issues are increasingly connected, and that makes early, coordinated planning especially important.

As your organization prepares for 2027, add these crucial decisions to the agenda.

How Will You Manage Healthcare Costs Without Losing Sight of Employee Value?

Healthcare affordability remains a central challenge for employers. The CBIZ Q3 Mid-Market Pulse reports that healthcare is now employers’ leading cost concern, while PwC projects commercial healthcare cost trend to reach 9% in 2027.

That pressure makes it tempting to focus mainly on premiums, employee contributions, and deductibles. A broader affordability strategy looks beyond the annual renewal and considers how plan design, pharmacy strategy, funding, claims trends, vendor performance, and employee communication work together.

2027 Action Items

• Model multiple renewal scenarios before renewal pressure peaks.
• Review pharmacy strategy, including PBM contracts, specialty drug controls, and GLP-1 coverage criteria.
• Use claims data to identify significant cost drivers.
• Evaluate whether current vendors are producing meaningful outcomes.
• Revisit whether your funding model matches the organization’s cost tolerance and risk profile.

The goal is to gain a clearer understanding of where healthcare dollars are going and where different choices could create greater value.

Are Your Benefits Delivering Value Employees Can Actually Use?

Offering a broad benefits package does not automatically create a strong benefits experience.

Employees may be managing student debt, starting families, caring for aging parents, preparing for retirement, or dealing with ongoing health needs. Those different circumstances are increasing the importance of benefits that employees can understand and apply to their own lives.

For employers, the opportunity is to examine both what they offer and how employees navigate those choices.

2027 Action Items

• Use workforce data, engagement surveys, and claims trends to identify benefits that are underused, misunderstood, or misaligned.
• Look at benefits through employees’ different life stages and financial priorities.
• Assess the tools and services employees use to navigate benefits and care.
• Connect financial wellbeing decisions with health and retirement choices.
• Track utilization, engagement, claims impact, satisfaction, and vendor performance.

This approach can help employers focus resources on the programs and experiences that employees are positioned to use.

Does Your AI Governance Match Your AI Adoption?

AI is quickly becoming part of everyday work. The CBIZ Q3 Mid-Market Pulse data cited in the Market Outlook Guide shows 63% of organizations are actively exploring, piloting, or implementing AI solutions. At the same time, 52% cite risk and governance concerns as a primary obstacle to adoption.

That tension creates an important planning question for 2027: Is organizational oversight keeping pace with AI adoption?

2027 Action Items

• Establish cross-functional AI governance involving HR, legal, IT, compliance, risk management, finance, and operations.
• Identify where AI touches employment decisions.
• Discuss how AI adoption may be changing the organization’s risk profile with your risk advisor.
• Train managers and HR teams on appropriate use, human oversight, and documentation.
• Review cyber controls for risks associated with AI-enabled work.

Clearer governance can help organizations pursue technology opportunities with a more deliberate understanding of the accompanying risks.

Do You Have the Workforce Capabilities Your Business Will Need?

For many organizations, workforce planning has traditionally centered on headcount: Who do we need to hire, and how do we retain them?

Planning for 2027 requires another dimension. Employers also need to understand how roles are changing and which capabilities their future business strategy will require. Technology, new skills, changing customer expectations, and evolving business conditions are encouraging employers to build more adaptable workforce models.

2027 Action Items

• Build an inventory of current workforce skills.
• Compare those capabilities with business priorities and AI adoption plans.
• Identify roles likely to change because of automation, technology, compliance complexity, or customer expectations.
• Develop clearer pathways for internal mobility.
• Connect training and upskilling investments to business outcomes.
• Consider where managed services may expand capacity or provide additional operational support.

Workforce planning becomes more useful when it focuses on the capabilities the business will need, rather than headcount alone.

Are Compliance Processes Ready for Greater Complexity?

Maintaining compliance continues to grow more complex amid expanding pay transparency requirements and developments affecting benefits and retirement plans, including the IRS’ 10.22% affordability threshold and updated HSA and high-deductible health plan limits.

Waiting for individual deadlines can leave HR, payroll, benefits, and leadership teams reacting rather than planning ahead.

2027 Action Items

• Develop a process for monitoring pay transparency, wage, and paid leave requirements across jurisdictions.
• Review ACA affordability calculations for 2027.
• Update HSA and HDHP materials to reflect applicable 2027 limits.
• Coordinate payroll and benefits administration needs.
• Review retirement plan governance.
• Maintain an HR compliance calendar to track critical dates and responsibilities.

A year-round approach can help organizations anticipate responsibilities instead of treating compliance as a periodic exercise.

Prepare for the Year Ahead With the 2027 Market Outlook

No organization will enter 2027 with exactly the same priorities. Some will be under greater pressure to manage healthcare costs. Others may need to focus on workforce skills, AI governance, compensation, compliance, or risk. The common thread is the need to look at these decisions together.

The 2027 Market Outlook Guide takes a deeper look at the trends shaping employer strategy. Subscribe to our HR and Workforce Insights to get this resource delivered straight to your inbox.