
The 2026 Open Enrollment Playbook: A Practical Employer Timeline
Get ahead of open enrollment with a practical employer timeline covering benefits, employee communications, payroll, HR technology and post-enrollment follow-up.

Get ahead of open enrollment with a practical employer timeline covering benefits, employee communications, payroll, HR technology and post-enrollment follow-up.

Work Friendly has been named to the 2026 Inc. 5000 list of America’s fastest-growing private companies. The recognition reflects our continued growth and the increasing demand for flexible, strategic people operations across HR, payroll, benefits, talent, technology, and compliance.

Poor benefits administration costs more than most employers realize. From payroll errors and compliance risks to lost productivity and employee frustration, learn where the hidden costs add up—and how managed benefits services can help reduce risk while freeing your HR team to focus on what matters most.

Payroll becomes significantly more complex as organizations grow. For one rapidly expanding healthcare technology company, year-end payroll involved equity compensation, Workday implementation, tax reporting, and strict compliance deadlines, leaving little room for error. Discover how Work Friendly partnered with the finance and payroll teams to navigate a high-risk payroll environment, reduce compliance risk, and successfully complete every critical milestone without missing a deadline.

Stay ahead of payroll deadlines with a practical payroll calendar designed for CFOs and finance leaders. Learn the key payroll, tax, compliance, and year-end planning milestones that help reduce risk, improve forecasting, and keep payroll running smoothly all year long.

As hiring accelerates heading into year-end, many businesses rely on independent contractors to move quickly. But classifying workers incorrectly can create significant legal, tax, and payroll liabilities. Here’s what every HR leader, founder, and CFO should know before Q4.