Her Story
About Michelle
Michelle R. Gray is a highly accomplished payroll and benefits leader with nearly two decades of experience supporting payroll, human resources, benefits administration, and workforce compliance. She currently serves as Corporate Payroll and Benefits Administrator for Sheehan Family Companies, a leading beverage distributor, where she oversees payroll and benefits operations across multiple divisions and states. Since joining the organization in 2018, Michelle has steadily advanced through key leadership roles, beginning with payroll and benefits administration for several divisions, earning promotion to Payroll Analyst in 2021, and ultimately being appointed to her current position in 2025 following the retirement of the company's benefits administrator Her expertise includes multi-state payroll compliance, ACA reporting, open enrollment management, retirement administration, tax reporting, HRIS systems, and payroll governance. Michelle's career journey reflects both dedication and a natural aptitude for the profession. Prior to joining Sheehan Family Companies, she spent a decade with DICK'S Sporting Goods, where she served in an administrative role that encompassed payroll, benefits, inventory management, workforce administration, and employee support. Although payroll was not originally a planned career path, she quickly discovered a passion for the field and found that her analytical mindset, attention to detail, and ability to thrive in deadline-driven environments made it a natural fit. What began as an unexpected opportunity evolved into a rewarding profession, allowing her to build extensive expertise through hands-on experience, continuous learning, and progressive leadership responsibilities. Known for her precision, problem-solving abilities, and commitment to compliance, Michelle excels at navigating the complexities of payroll and benefits administration in an ever-changing regulatory landscape. She is particularly skilled at managing multi-state compliance requirements, ensuring organizations remain aligned with evolving employment laws, tax regulations, and family leave programs. Michelle takes pride in creating efficient processes, supporting employees through critical benefits programs, and fostering collaboration across departments. Her ability to balance operational excellence with employee-focused service has established her as a trusted resource within her organization and a respected leader in payroll and benefits management. Outside of her professional responsibilities, she enjoys travel, which reflects her appreciation for new experiences and continued personal growth.
Her Interview
Ten minutes with Michelle
01What do you attribute your success to?
I believe in myself and I know I can do whatever I set my mind to.
When I first started out, I was nervous. I had spent a lot of time at home raising my children and hadn’t been in the workforce for very long. I remember applying for jobs thinking no one would hire me because I didn’t have the experience.
But when someone gave me that first opportunity, I made the absolute most of it. I worked hard, stayed determined, and kept moving forward.
At Sheehan Family Companies, I showed up, put in the work, spoke up, shared my ideas, and stayed committed to growing. That mindset helped me earn two promotions in 8 years and become the person I am professionally today.
What I’ve learned is that hard work, determination, and believing in yourself can take you farther than you think. Don’t count yourself out because your path looks different or because you’re starting later than others. Keep going, keep learning, and trust yourself.
I’m proud of how far I’ve come—and I’m always looking toward the next step, the next challenge, and the next opportunity.
02What’s the best career advice you’ve ever received?
You can do it. Just put your mind to it and keep working toward your goals. There will be moments when you doubt yourself, but don’t let those doubts define what you’re capable of achieving.
I’ve been fortunate to have people in my corner who believed in me, especially a woman I worked with at DICK'S Sporting Goods. No matter where life or work took either of us, we always stayed in touch and remained close. She has been one of my biggest cheerleaders throughout my career.
Every time I earn a promotion or something positive happens, she’s one of the first people to reach out with congratulations and encouragement. Her support has meant so much to me over the years. She’s not only a wonderful friend but also an incredible mentor who has always reminded me to believe in myself and keep reaching for more.
Having someone who believes in you can make a difference, but the most important thing is learning to believe in yourself. Work hard, stay determined, and don’t be afraid to pursue the next opportunity. You may be surprised by just how far you can go.
03What advice would you give to young women entering your industry?
Take your time and believe in yourself. No matter where you come from or where you’re starting, there is always opportunity out there if you’re willing to look for it and work hard for it.
When I first started out, I was very nervous because I hadn’t been in the workforce for very long. I had spent a lot of time at home raising my children, and stepping back into a career felt intimidating. When you first put yourself out there, it can feel scary and uncertain.
But I learned that growth doesn’t happen all at once—it happens by showing up, working hard, staying determined, and believing you belong. Every opportunity builds confidence and opens the door to the next one.
A lot of hard work and determination can take you farther than you imagine. Trust yourself, keep moving forward, and remember—you can do whatever you set your mind to.
04What are the biggest challenges or opportunities in your field right now?
One of the most challenging parts of my role is keeping up with all of the new laws and the way things continue to change and evolve each year. Because we have different divisions across multiple states, there’s a constant need to stay informed and understand new regulations and how they apply in different locations.
At the same time, many of these changes are incredibly positive—especially for families and for women having children. Programs like family and medical leave, along with the growing number of state-specific benefits and protections, have expanded significantly and can make a meaningful difference in people’s lives.
The challenge is keeping up with all of the nuances and understanding how each state approaches things differently. It’s always evolving, so it requires continuous learning, adaptability, and staying ahead of change.
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