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HR/Payroll Solutions SVP: “Communication is Key” for a Successful Year-End 

Christopher Wood, CPP  

· 6 minute read

Christopher Wood, CPP  

· 6 minute read

As the end of the calendar year approaches, businesses embark on the crucial task of finalizing their payroll processes. Year-end payroll is not merely about closing the books but a comprehensive undertaking that requires meticulous attention to detail, adherence to legal requirements, and seamless coordination among various departments.   

When it comes to successfully navigating the various tasks, processes, and responsibilities of payroll year-end, Tom Rose, Senior Vice President, Customer Success and Operations, at TriNet, a cloud-based professional employer organization for small and medium-sized businesses, emphasized that “communication is key.” 

“I’ve been through a lot of what we call ‘year-end, year-start’ because there’s not only actions and things you really need to focus on at the end of the year, but it’s also preparing for the beginning of the following year,” Rose explained. 

Complexities of payroll year-end 

As any payroll professional knows, this complex annual process is a multifaceted procedure encompassing various elements and modifications, from tax calculations to compliance with ever-evolving regulations. “It changes year-over-year and there’s more of those changes – it’s not less,” Rose stressed.    

For example, Rose pointed to the complexities regarding the significant shift to a more remote and hybrid workforce during, and even after, the COVID-19 pandemic where having an in-depth understanding of multi-state payroll laws and regulations has become crucial for payroll professionals. 

According to the U.S. Bureau of Labor and Statistics (BLS), about 15% of individuals worked full workdays at home before early 2020. That percentage increased sharply to nearly 40% during the height of the health emergency. As of August 2023, the BLS said that about one in five (19.5%) individuals worked remotely for wages, showing an overall net gain in remote work from before the pandemic.   

“[Increased remote work has] added a lot to the year-end processing,” Rose noted. “There’s guidelines and rules within each state on how they work and how they interact.” 

Accuracy of employee data  

Being hyper-focused on the accuracy of employee data is one of the most important components of a successful year-end. This data frequently serves as the bedrock for tax calculations, benefit management, and information reporting. 

“At the end of the year, it’s making sure that employees are focusing on their statements, their earnings, [and] the way things are being calculated,” Rose said, adding that employers should advise employees to check their personal and withholding tax information for accuracy before the end of each year to reduce the need for filing corrected information and employment tax returns down the road. 

“Make sure that it all ties out in November, December and is clean for that break going into the following year,” he explained. 

Balancing artificial intelligence 

As a way to help minimize errors and speed up certain tasks associated with payroll year-end, some businesses are implementing next-generation artificial intelligence (AI). From an AI perspective, Rose thinks that there are things that are very “black and white” when talking about taxes and structures. However, he also believes that when it comes to the security around payroll information, there remains a critical human component. 

“I don’t want to minimize AI. I think there’s a future there. There’s another level of support,” Rose began. “But it’s still that human interaction that’s so important when you talk about these sensitive topics.” 

This is also important when it comes to compliance as the Equal Employment Opportunity Commission (EEOC) announced a first-of-its-kind settlement regarding an AI-related employment discrimination lawsuit in September 2023. President Biden issued an executive order on AI at the end of October 2023, and a congressional subcommittee held a hearing on AI and the future of work on October 31. Payroll-related AI laws may become a reality in the near future, adding another layer of compliance to the industry and the year-end process. 

Ensuring payroll compliance 

Payroll compliance comes in many forms across multiple departments in a business. It relates to taxes and labor laws that all come to a head at the end of each year. “We hear the horror stories of a simple misclassification that snowballs and becomes this big thing,” Rose said, regarding considerations related to the employer-employee relationship.   

The U.S. Department of Labor is expected to issue a new, more employee-friendly worker classification rule soon. As with remote work and other complicated topics relating to payroll, there are often multiple rules to consider at the federal, state, and local levels.   

To alleviate fear or stress related to compliance concerns, Rose recommends a well-educated payroll workforce and other partnerships to set a business up for success. “If you really focus on the details and you have the right partnerships, you’ll set yourself up for success,” he said, adding that the process of payroll compliance does not stop after December or January. “The changes will continue through the course of the year and you just need to be nimble.” 

Conduct a payroll year-end retrospective 

On the tail end of payroll year-end, in order for an employer to examine their payroll year-end process to see what worked and what needs work, Rose recommends businesses conduct a retrospective meeting. This will help shine a light on areas where improvement is required for the next year-end. “You want to improve every year,” Rose stated. “We’re constantly adjusting and constantly learning from how we [process year-end].” 

A typical payroll year-end retrospective should include reviewing accomplishments and milestones, assessing any challenges and obstacles, extracting lessons learned, implementing improvements, encouraging feedback and collaboration, and setting goals for future success. 

Make sure to analyze the process for reviewing and updating employee information, as this can be the cause of errors discovered after the fact. Also, review the payroll records to check for discrepancies, benefit reconciliation, and proper payment of bonuses and other compensation to avoid tax reporting errors. In addition, keep track of any changes in tax laws or regulations that might affect the upcoming year-end at the federal, state, and local levels. 

Continue year-end success with communication 

In closing, Rose again stressed the importance of communication when it comes to a successful payroll year-end. “[It’s] the busiest time of the season…[and] you’ve got to continue to communicate to the employees that the actions they need to take will really set that payroll expert up for success,” Rose explained.   

He added that continuous reminders and year-end training based on analysis and data from previous end-of-year payroll processing will help mitigate errors; and to pay close attention to the small things since they have the potential to develop into much bigger issues throughout the year. 

To learn more about how Checkpoint’s payroll solution can help your business, visit 

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