Cirrus Payroll is a full-service payroll provider for small businesses. The company was founded in 2012 and has grown its presence nationwide. We spoke with Tyler Winn, Cirrus’ president and founder, to learn more about him and his business.
Tell us about yourself and Cirrus Payroll.
I’m a Tulsa native, born and raised here by my wonderful parents. I’m raising my family here as well. My wife Monica and I have been married for five years now, and we have two beautiful sons, Wesley (three years old) and Elliot (six months).
Cirrus Payroll has been in business since 2012. We make it easy for the small business owner to outsource all the risk and complexity of payroll processing and payroll tax compliance. Since day one, we’ve been laser-focused on the small business owner. Most of our clients have less than 25 employees. We love serving that segment of the market.
We're a local payroll service – most of our clients are in the state of Oklahoma – but we have a national presence as well, processing payroll in more than 40 states. I’m a CPA that only offers payroll (no accounting or tax), and that’s rare. A lot of other CPAs around the country have seen what we’re doing and have decided to partner with us to process payroll for their clients.
When did you know you were ready to start your own business?
I’ve had entrepreneurial leanings since my teenage years. I was reading books on business and economics even back then. In college, I started an online book exchange business for students to buy and sell textbooks from each other, rather than going through the campus bookstore (I could have been the next Amazon…oh well). After college, I knew it was time to take the leap into business ownership. I was dreading going to work Monday through Friday, but on Saturdays, I was jumping out of bed to work on side gigs I had taken. It was an itch I just had to scratch.
What advice would you give to young professionals thinking about starting their own business?
If you want to grow a business, you have to grow as a person. Business growth presents a constant stream of new challenges that you can't overcome if you remain the same person you were yesterday. To meet these challenges and succeed, you must perpetually strengthen your mindset and learn new ideas. Invest in yourself. Read books. Listen to podcasts. Go to conferences. Spend time with people who are smarter and more successful than you. If you commit to being a lifelong learner, success will be a byproduct.
How do you set yourself apart from your competitors?
Hiring and retaining great employees. Nothing sets you apart like the quality of your team. I see some of our larger competitors experiencing high employee turnover. Every time they lose an employee, that knowledge and experience walks out the door. On the flip side, the longer I retain my amazing team members, the stronger we become. For that reason, employee happiness is a top priority for me. I enjoy getting creative to show my appreciation. For example, my employees work from home. Because that’s their “office,” I pay for a house cleaning service to clean their homes every two weeks.
Tulsa was recently ranked as one of the best cities to start a business. Why do you think Tulsa is a great place for entrepreneurs?
Tulsa somehow provides this unique mix of big-city opportunity with small-town community. It’s a big enough place to cast a wide net over a lot of potential customers, but small enough that reputation matters. If you do business with integrity, people will notice and want to do business with you. We’ve been in business for eight years, and always doing the right thing for our customers and employees has helped us build incredible momentum.
Where do you hope to see Cirrus Payroll in five years?
We have a good thing going. Small business payroll is what we do best, and I have no plans to try and expand into a ton of other related services or go after bigger fish. I’m a big believer in specialization and staying in your lane. I see us doing the same things we’re doing now, but with more clients and an expanded team! We’ll continue to improve the quality of our service over time.
You enjoy visiting different coffee shops around Tulsa – what’s your favorite?
My favorite place to work right now is DoubleShot’s new location on Boulder Avenue. The space is beautiful with tons of natural light. I get there every Monday morning when they open at 7 a.m. to plan out my week with a cup of coffee and a sausage roll. It’s a peaceful place to think and get work done.