Our team is committed to delivering exceptional payroll and HR services, specifically tailored to meet the needs of small businesses. We care deeply about our clients’ success, and we take our role in helping grow their business seriously.
Cirrus Payroll was founded in 2012 by Tyler Winn, a CPA who witnessed firsthand what happens when small businesses don’t get the payroll support they need.
As an accountant, Tyler understood the standard that CPAs hold themselves to. He also understood how frustrating it was to refer clients to payroll companies that were slow, impersonal, and impossible to reach. So he built something different.
The idea was simple: give small business owners the kind of personalized attention they deserve, with real humans who respond fast and actually care about getting it right. More than a decade later, that’s still exactly what we do.
“It sounds crazy, but we actually love payroll. And we love to help. I founded Cirrus Payroll more than a decade ago because I wanted to give small business owners and their accountants the kind of personalized attention they deserve. I’m truly passionate about helping make our clients’ lives easier while creating a happy work environment for our team.”
— Tyler Winn, Founder & CEO
Payroll should disappear into the background. You shouldn't have to think about it, worry about it, or spend time on it. When we're doing our job right, you never do.
We have a role to play in helping your business grow, and we take it seriously. With more than a decade in business and nearly 100 years of combined payroll experience, you can trust our team to get the job done—right.
The following is our Vivid Vision, a blueprint for the future of the company. This vision brings the future into the present, providing us with a crystal-clear understanding of where we are headed.
This clarity empowers us to make better decisions in the present, ensuring that every action we take is strategic and aligned with the reality we are seeking to create.
Our core values aren’t just words on a wall. We talk about them often and we live them out every day.
We respond quickly, communicate clearly, and provide consistent updates so clients always feel informed and confident we're on it.
We relentlessly follow through on problems, tasks, and commitments until they are fully resolved. When you bring something to us, it doesn't fall through the cracks.
We bring positive, helpful energy to every interaction. Payroll might be stressful, but working with us never is.
We’d love to meet you. Start with a quick quote. No obligation, no pressure.
After several years in public accounting and consulting, Tyler started his own bookkeeping business in 2011. He quickly began to witness his clients struggling to find payroll solutions that made their lives easier. So he decided to offer payroll services himself. His clients loved it, and Tyler found his entrepreneurial calling. He founded Cirrus Payroll the following year, to give business owners a personalized alternative to the national payroll bureaus.
Tyler’s passion goes beyond the numbers. He loves building businesses, serving clients, and creating happy teams. He is a self-improvement junkie and is constantly thinking of ways to improve all aspects of the company.
Tyler has been featured in publications such as the Journal of Accountancy, Accounting Today, Clutch, and the Thriveal CPA Network Podcast. He is a finalist for Young Entrepreneur of the Year in his hometown of Tulsa, Oklahoma.
Tyler is happily married to Monica and they are both loving life with their two boys. In his free time, you might find Tyler hanging out in coffee shops around Tulsa, traveling the country, volunteering with his church, or around the BBQ with his brothers.
Desiree has a background in payroll and client services. She is a Puerto Rico native, however, has spent much of her life in Orlando, FL. Desiree loves to be challenged and is passionate about self-progression and helping others. She is self-motivated and driven by her love for learning and taking initiative.
In her free time, you can find Desiree exercising, sewing, traveling or at the playground/adventuring with her husband, Johan and daughter, Skylar.
CPA Channel Partner
With a strong background in payroll & HR solutions, Moniquak brings a consultative, relationship-driven approach to helping businesses streamline their operations. She specializes in working closely with CPA partners and small business owners to simplify payroll processes, ensure compliance, and create scalable systems that support long-term growth.
Known for her responsiveness, attention to detail, and commitment to service, Moniquka (Moe) takes pride in delivering solutions that are both efficient and tailored to each client’s unique needs. She is passionate about building lasting partnerships and helping clients feel confident in the systems that power their business.
Executive Assistant
Trish’s background includes working in compliance (AML/KYC), bookkeeping, project management, and office administration. She has a double degree in Business Economics and Marketing Management. Trish takes pride in her ability to balance both the people side and the quality control side of various projects. She is passionate about process improvements and has a knack for simplifying complex systems.
Trish’s hobbies include traveling, finding hidden gems, and cafe-hopping! Currently, she is living her best life working remotely.
Autumn has experience with payroll, HR and customer service. She grew up in the suburbs of Chicago and graduated from Illinois State University with a degree in Communications and a focus in Human Resource Management. Autumn is motivated by my eagerness to learn and the satisfaction of helping make other people’s lives easier.
Autumn likes to spend my free time outdoors, hiking through nature preserves, or taking my paddle board out on the lake.
Her hobbies include playing video games, crocheting, and taking care of my 3 cats Josie, Whiskey and Winnie.
Payroll Specialist I
Chantel started her payroll journey in 2022 after many years in customer support and client retention. Completing her FPC in 2023, she feels passing payroll knowledge to small businesses will help them succeed. In the future she wants to find new ways to help businesses stay efficient through payroll processing. She is currently in Virginia Beach, VA with her two kids. Most free time is spent on outings with her children following a learn through experience model.
