Voices of Check: Head of Education Tisha Winfield

February 15, 2024
Tisha Winfield

Head of Payroll Compliance

Tisha Winfield

After graduating from Rutgers University, I, like many recent college graduates, found myself needing a job and at a crossroads: starting a career in public service or one in payroll. I’ll be honest–I didn’t have an immediate passion for payroll, but out of necessity, and being a recent business management graduate who enjoyed math, I set off on my journey in payroll. Payroll may not be the flashiest career choice, but it was a way to pay the bills and that was enough for me. As the years passed, I began to manage new projects, mentor new hires, and lead teams. I was excelling in all areas of payroll and expanded my portfolio to include implementation, HR, and tax filing. Twenty-five years and four payroll companies later, I guess I can consider myself a subject matter expert. 

About 4 years ago, I made one of the most pivotal decisions of my career: joining Check. The decision was so out of character that I initially turned down the opportunity. I’d just gotten to a point where I felt financially stable, I was a few years away from being an empty nester, and I was really good at my job. Leaving my safety net and joining Check meant dedication, risk, and challenges. Those challenges are what ultimately made me decide to join Check. How could I pass on an opportunity to be a disruptor?

Payroll is built on regulations and processes that have been in place for over six decades. And while not much has changed around the basic payroll rules, it is still extremely difficult to parse through those rules and create a product that is easy for an employer to use. Creating a more customized all-in-one solution with a singular customer profile disrupts the strategy of legacy companies that rely on being able to sell to any employer needing payroll services. 

I was Check’s 13th hire. My role from day one spanned from determining the best way to support a tax or form to something as daunting as building a team. Each of the roles that I’d previously been in were already established. The product was built. The team was cohesive. Processes were in place. Yes, I’d have opportunities to enhance the product and grow teams. But, at Check, I had the opportunity to start from the beginning. I was in the room, making decisions that affected the future of the company. I was able to influence our product in a way that balanced requirements and innovation. 

I would be remiss not to mention the many great mentors and leaders that I’d worked with in the past, from whom I took inspiration in order to model what I wanted my role to look like as the Head of Payroll Compliance. Yet, I still had to pave my own path because many of them had not done this at a startup. But payroll is payroll, right? Well, I learned quickly that startup life is different. I had to learn so many new terms that I started my own glossary! 

While the adaptation is challenging, it’s also inspiring. It lets me know that I can shape myself into the type of leader that requires embracing change, stepping into unknown territory, and figuring things out all while a business is growing around you. 

My work at Check was exciting. I loved the work that I was doing. The responsibilities that I had gained. The career path that I was on. But startups can be grueling and leaving work at the office is not possible when your home is your workplace. Instead of giving up, I stepped back and reflected on what I wanted from work and for life outside of work. I found a hobby in ceramics and scheduled that time into my week. I made time again for friends and family dinners. I stopped looking forward to the next vacation and took a day here and there to recharge. Check gave me the space to become a better version of myself. Ultimately, I became a more balanced leader, able to prioritize the biggest areas of impact at work without needing to be a part of every solution. 

Joining Check so early allowed me to influence the type of culture I wanted to be a part of. Being the first Black employee to join Check, I wanted to ensure that we created a space for others who would follow to feel as though they belonged. I also wanted to share my culture with those that I worked alongside every day. I began the tradition of celebrating Black History Month by sharing my family’s history including my Afro-Caribbean heritage, the history of Black Greek-lettered organizations, and soul food. I posted a story every day for all 28 days of the month. Since then, we have asked volunteers from all backgrounds to share the story of a Black historical figure. 

Our early grassroots efforts also helped to set the stage for our Diversity, Equity, Including, and Belonging (DEIB) leaders and Employee Resource Groups (ERGs). There are countless “firsts” and “onlys” in early tech companies, especially in leadership. Early-formed ERGs are mostly allies with few impacted members. The greatest tension I felt was the need to grow the company quickly and still focus on diversity. And while the Black ERG is small, we have a mighty impact on the company. I’m proud of our work and the space we’ve created at Check. It’s a small way to take a stance and say that we, too, belong in tech. 

If you told me when I was 22 that I’d be spending decades working in payroll, I’m not sure I would have believed you. And if you told me that I’d love my work, I’d be shocked. I thought when I took my first job in payroll, I was doing it for that steady paycheck. While that may have been true, my career at Check has proven to mean so much more. I go to work every day to support our effort to pay people across the country, but I also have the privilege to lead our team in continuing to build a culture that I’m proud of.

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