Legacy Tribal Services Leadership

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I was born and raised in Tulsa, Oklahoma.  I played baseball for Phillips University in Enid and Northeastern State University in Tahlequah, where I graduated with a degree in Biology and a minor in Chemistry.  I then received a Master’s Degree in Educational Administration while teaching high school science at Union Public Schools.  Since then I have been employed as a Market Executive for a Fortune 500 company, started Legacy Wealth Management, a truly unique financial services company, and launched Legacy Risk Management, a property & casualty insurance agency.

My wife Becca and I have been married for seventeen wonderful years and we have three children: Emerson, Jax, and Hayden.   My wife is a full-time mom and loves every minute of it. 

As the president of Legacy Tribal Services, my goal and promise to our clients is to provide them with simple solutions and uncommon service in an ever-changing healthcare environment.  Our agents, managers, and staff are committed to educating and empowering our clients.  We will provide guidance and expertise while delivering value to meet your specific needs.

Tyler Winn is a CPA, but not the stereotype. He loves building businesses, serving customers, and creating happy teams. He has been featured in publications such as the Journal of Accountancy and Accounting Today as an expert in his field.

Tyler was born and raised in Tulsa, Oklahoma. He graduated from Hillsdale College in Hillsdale, Michigan, with a degree in Accounting, and earned his CPA license while working at Deloitte, currently the largest accounting firm in the world. He started Cirrus Payroll in 2012, a payroll service company which has quickly grown to serve hundreds of small businesses across the country. He is excited to bring his strengths and experience to Legacy Tribal Services.

Tyler married his lovely wife Monica in 2015. They currently have one son Wesley (2), with another boy on the way.

 
I was born and raised in Tulsa, Oklahoma. I played rugby for Oklahoma State University where I graduated with a degree in Finance and a minor in Accounting. Since then I have married my wife, Erica, had three children Rory (4), Sydney (3) and Reince (2) and have built a career in the  Medicare insurance industry.

As Enrollment Services Director, I am privileged to meet with individuals every week to discuss insurance needs in today’s ever-changing benefits environment.  Our approach is centered on education first.  I pride myself on that and our clients recognize the difference in our company's unique approach to working with them from the very first time they sit down with us.