Selling Season in the Payroll Industry

January 8, 2024
Dylan Munn

Partner GTM Strategist

by 
Dylan Munn

In the dynamic world of payroll, it's widely believed that almost a third of businesses in the United States make the bold move to switch their payroll provider each year. What's even more fascinating is that often more than half of these transitions take place during a time that we affectionately call "Selling Season."

Between August 15th and January 15th, business owners, CFOs, and HR departments reevaluate their payroll vendor with the goal of securing a superior product and experience compared to their existing offering. Organizations encounter payroll providers that fail to meet their standards, impeding overall business growth, and consequently driving companies to transition to a new provider to rectify payroll issues for year-end tax purposes or to begin the upcoming tax year with a trusted vendor known for superior performance. These factors to clean up payroll data or embark on a fresh start in the new year is the force behind what we refer to as the Selling Season.

As we wrap up the 2023 selling season, let’s review the reason Selling Season exists and a few strategies to a successful sales cycle. 

Why Selling Season Exists

It’s not a coincidence that a majority of payroll switcher companies are making that change in the same few weeks. Switching a payroll provider is no small feat and there are many considerations that go into the decision.

In our blog “The End of Days: Terminating Your Payroll Provider”, we discuss timing as one of the key considerations for termination. Companies need to ensure that paychecks to their employees aren’t affected, benefits stay consistent, and all the data is transferred over cleanly and correctly.

Switching payroll providers in December or January allows businesses to start fresh with a new system at the beginning of a new fiscal year. They’re able to keep financial records organized and make taxes and other year-end paperwork easier because year-end is the natural cut-off for most financial, payroll, and benefit records.

Implementation Timeline

While many companies are switching payroll providers in the same few weeks, some are looking to switch for that same year and some are looking ahead a year. The reality is, payroll implementations are complex and involve dozens of critical, time-sensitive milestones, requiring action from several stakeholders.

With the dual pressures of cleaning up this year or starting fresh next year with their payroll vendor, a payroll sales rep needs to deal with the full spectrum of buyer personas: from those who select their next year’s vendor a year in advance and bring their own implementation plan to those who have put it off all year and now need an implementation exception made because it’s mission-critical they process payroll with a new vendor in the next 3 days.

The key consideration that impacts all buyers in between these poles of payroll buyers is they all must be managed through implementation. The year-long implementation team can have turnover, change in priorities, and black-swan impacts to their business, while the rushed implementation needs to understand the importance of following every instruction provided in a quick and effective manner.

Having a clear implementation track with all parties involved in the process operating on the same cadence and timeline addresses the full variety of buying times. Providing a distracted employer with an understanding of where they are in the implementation process, who has the next action item, and what the next steps are allows for accountability to move a sales opportunity efficiently through the implementation process. However, it’s easier said than done. This is more art than science and with any art, experience and talent are needed to produce a beautiful output.

Check is a partner through and through

Switching to a new payroll provider at the start of a new calendar year is ideal for employers. Doing so coincides with the natural transition of financial and tax records, allowing for a straightforward shift from the previous year's data and aligning with the annual reset of payroll calculations, thereby minimizing complications and potential errors.

If an employer encounters issues with their current provider, such as errors in payroll processing, lack of essential features, or poor customer service, they may decide that the benefits of switching to a more capable provider outweigh the challenges of a mid-year transition. This approach ensures that businesses maintain their operational effectiveness, prioritizing the immediate needs and satisfaction of their employees over the convenience of a calendar-based change.

Either way, Check’s Partner GTM Strategy team tells their Partners’ sales team the same thing, “Our job is to help you sell more bigger deals faster.” Through working with Check’s Partner GTM Enablement team we support our Partners by creating full content strategies for Selling Season, as well as guidance on how to ensure their off-season pipeline is equally impactful to the growth of their payroll business. No matter the time of year, the macro changes in the marketplace, or industry specific trends Check’s GTM team provides a number of unique tools to help our Partners’ sales team members hit and exceed their quotas.

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