HR/Compliance Challenges by Company Size: 25 to 50 Employees

July 14, 2025

As your team grows to 25-50 employees, the HR and compliance challenges you face become more complex. This is often the stage where businesses start to trigger new regulatory thresholds, such as ACA (Affordable Care Act) and FMLA (Family and Medical Leave Act), and where managing employees in multiple states can add significant complexity.

Key Challenges for 25-50 Employees:

  • State-by-State Compliance: As your team expands and you hire remote workers, understanding and adhering to labor laws in each state becomes critical.


  • Need for Scalable HR Systems: It’s time to transition from ad hoc HR practices to formal HR systems, such as HRIS, PTO tracking, and consistent policies.


  • Leadership Shift: As the business grows, leadership needs to shift from handling HR tasks informally to implementing structured HR processes.

Likely HR Headaches:

  • COBRA Administration: Ensuring compliance with COBRA rules for health insurance coverage after employee terminations.


  • Employee Relations & Performance Issues: As the team grows, managing employee performance and handling disputes becomes more complex.


  • Discrimination/Harassment Claims: Ensuring a safe and respectful workplace requires robust systems to handle any employee complaints.

How a PEO Helps:

  • Centralized HRIS System: A PEO provides you with a centralized system to streamline HR processes, making managing a growing team more efficient.


  • Built-in Compliance Infrastructure: With a PEO, your business is automatically compliant with multi-state labor laws and federal regulations, reducing the risk of audits and fines.


  • EPLI Insurance: Employment Practices Liability Insurance (EPLI) protects your business against claims of discrimination or wrongful termination.

Pro Tip:

There are over 600 PEOs nationwide. Work with a PEO Broker (like us!) to get side-by-side comparisons and unbiased guidance—at no cost to your business.

Need help getting started?

📧 Email: Suzanna@PEOForTheCEO.com

📅 Book a free consultation: https://calendly.com/suzanna-yourpeoadvocate

Stay tuned for the next post in this series, where we’ll dive into HR challenges for businesses with 55-100+ employees!