About Us
Jonathan Michaels, Founder and Principal
Jonathan Michaels is the Founder and Principal of Michaels Strategies, a boutique consulting firm focused on the North American gaming industry.
Prior to founding the firm, Jonathan served as Senior Vice President, Strategic Development & Government Affairs for Sightline Payments, the U.S. sports betting and casino gaming market’s leading digital payments provider and mobile app developer. In the role, Jonathan led government and regulatory affairs to advocate for expanded digital payments options across the North American gaming industry. He also oversaw Sightline’s corporate communications and helped build new business relationships to leverage Sightline’s products into new markets and verticals.
Jonathan began his tenure in the gaming industry at the American Gaming Association (AGA), the national trade group for the U.S. casino industry, serving as Vice President, Strategic Alliances. During his more than six-year tenure at AGA, Jonathan led AGA’s membership and partnership efforts focusing on growing and diversifying the association to be more representative of the gaming industry, which resulted in AGA’s first tribal members. Jonathan also played an integral role in developing the association’s strategy around payments modernization and sports betting, including creating the AGA Sports Betting Executive Summit.
Jonathan has been the recipient of several awards, including the American Business Awards Silver Stevie for Communications Professional of the Year and the Global Gaming Business 40 Under 40 for 2021.
Jonathan also served in development roles at the Sports & Fitness Industry Association and the University of Maryland.
Jonathan is a proud alumnus of the University of Maryland, where he received a Bachelor of Arts degree in government and criminology. He currently lives in Bethesda, MD, with his wife and three children.
Shipley Michaels, Head of Security and Chief Bark-eting Officer
Shipley Michaels is the heart and soul of Michaels Strategies. He began his role as a Security Officer in November 2016, was promoted to Head of Security in 2017, and added the role of Chief Bark-eting Officer upon the founding of the firm.
Shipley is a cockapoo who was adopted from Southwestern Virginia via Homeward Trails Animal Rescue.
Sarah Michaels, Head of Licensing and Compliance
Sarah Michaels joined Michaels Strategies in 2026 to assist companies with gaming licensing matters.
Prior to joining Michaels Strategies, Sarah served in paralegal and legal support roles for a commercial and civil litigation practice and a family law practice, helping clients work through complex matters while managing sensitive information.