Meet Our Leadership
Matthew Cullen
Principal and Chairman of the Board
Matthew Cullen
Principal and Chairman of the Board
Matthew P. Cullen is a businessman, community leader and philanthropist who serves as the Executive Chairman and lead investor of JACK Entertainment. His leadership has been central to the growth and development of JACK’s urban casinos, fostering a company culture that prioritizes community commitment and sustainable growth. He is also active in a variety of venture and private investments including significant real estate development projects domestically and abroad.
Previously, Cullen spent more than a decade leading gaming, real estate, and other initiatives for Dan Gilbert’s Family of Companies helping to oversee the multibillion-dollar redevelopments of Detroit and Cleveland. Additionally, Cullen spent 30 years in senior executive positions with General Motors during which time he had responsibility for their global real estate portfolio.
Cullen has been a leader in the resurgence of the City of Detroit, having served as the founding Chair of the Detroit RiverFront Conservancy and Chairman of Invest Detroit. He is a board member of the Penske Corporation, Downtown Detroit Partnership, Detroit Regional Chamber, Hudson-Webber Foundation, and Detroit Regional Partnership and a trustee of the College for Creative Studies and the Community Foundation for Southeast Michigan. He previously chaired the Detroit Metro Convention & Visitors Bureau, The Parade Company, The Metropolitan Detroit YMCA, Michigan Economic Development Corporation and CoreNet Global. He also serves as the Chair of the Matthew and Karen Cullen Family Foundation.
Cullen earned a degree in economics from the University of Michigan and an MBA from the University of Detroit Mercy. He also completed the Senior Executive Program at Harvard University.
Mark Dunkeson
Principal, Chief Executive Officer, and Board Member
Mark Dunkeson
Principal, Chief Executive Officer, and Board Member
Mark Dunkeson is the Chief Executive Officer of JACK Entertainment, where he has led transformative changes in the operations and company culture since joining in 2013. As both an owner and a member of the board of directors, he plays a critical role in shaping the strategic direction and growth of the organization.
Dunkeson has spent 30 years in commercial gaming, resort, and hospitality development field, where he led operations for several multi-property divisions of Red Rock Resorts in Las Vegas, Nevada. As Senior Vice President of Operations for the luxury brand division, he oversaw operations of properties that included Red Rock Casino, Resort and Spa and Green Valley Ranch Resort, Spa and Casino. Prior to that, Dunkeson led and operated seven other gaming properties for Red Rock Resorts and spent five years as their Corporate Vice President of Development, spearheading the company’s expansion initiatives. Additionally, he served as the President and Chief Operating Officer for Bedrock Detroit LLC, a transformational urban core real estate investment, development, and operations company with over $5 billion deployed with more than 20 million square feet of office, retail, and residential space. In addition to focusing on JACK Entertainment, Dunkeson is currently involved in multiple significant hospitality projects in Guanacaste, Costa Rica.
Dunkeson received his Bachelor of Arts and Sciences in Psychology from New Mexico State University.
Glen Tomaszewski
Board Member
Glen Tomaszewski
Board Member
Glen Tomaszewski is the Executive Vice President and Chief Financial Officer of JACK Entertainment, where he oversees the company’s financial operations, including financial planning and analysis, accounting, and treasury functions. Since joining JACK in 2015, Tomaszewski has been integral in guiding the company’s financial strategy and supporting its growth.
With over 30 years of financial expertise, including more than a decade in the commercial gaming and hospitality sectors, Tomaszewski brings a wealth of experience to his role. Prior to entering the gaming industry, he spent 15 years in the retail industry, where he held a variety of key financial leadership positions.
Tomaszewski earned both his bachelor’s and master’s degrees in business administration from the University of Michigan’s Stephen M. Ross School of Business and is a certified public accountant.
Chad Barnhill
Executive Vice President and Chief Operating Officer
Chad Barnhill
Executive Vice President and Chief Operating Officer
Chad Barnhill is the Chief Operating Officer of JACK Entertainment, where he has been instrumental in driving operational performance and the growth of JACK’s properties since joining in 2015. Prior to this role, he served as Senior Vice President of Regional Operations for JACK properties in Detroit and Cincinnati, where he played a key role in shaping strategic initiatives and overseeing regional development.
With over 30 years of experience in the gaming industry, Barnhill has held a range of executive roles, overseeing areas from marketing to hotel operations. His previous leadership as Vice President and General Manager of Horseshoe Casino Baltimore included guiding the design and development of the prominent casino near Baltimore’s Inner Harbor.
A dedicated advocate for the communities JACK serves, Barnhill emphasizes a commitment to community engagement and corporate responsibility. He actively supports the Cleveland area by serving on the Boards of Directors for the Greater Cleveland Partnership, the Rock and Roll Hall of Fame and the Greater Cleveland Sports Commission.
Barnhill holds a bachelor’s degree in marketing from Millikin University and an MBA from Western Kentucky University.
Angela Matthews
Executive Vice President of Corporate Operations and General Manager of JACK Cleveland Casino
Angela Matthews
Executive Vice President of Corporate Operations and General Manager of JACK Cleveland Casino
Angela Matthews serves as Executive Vice President of Corporate Operations for JACK Entertainment and General Manager of JACK Cleveland Casino. Since joining JACK Entertainment in 2016, she has been instrumental in advancing gaming operations across all JACK properties, bringing a strategic focus and operational excellence to the role.
With over 20 years in the gaming industry, Matthews has a wealth of experience in slots, marketing, and executive management. Prior to joining JACK, she served as General Manager of Avi Resort & Casino in Laughlin, Nevada, and spent 15 years with Station Casinos LLC, where she held key leadership positions, including Director of Slots and Director of Marketing.
Matthews holds both a bachelor’s degree in financial management services and a master’s degree in finance from the University of Las Vegas.
Mark Miller
Executive Vice President of Strategy and Corporate Development
Mark Miller
Executive Vice President of Strategy and Corporate Development
Mark Miller serves as the Executive Vice President of Strategy and Corporate Development at JACK Entertainment, where he drives the company’s strategic direction and is responsible for identifying and executing new growth opportunities and investments. Since joining in 2011, Mark has played a pivotal role in JACK’s success and evolution as an organization.
Previously, Mark served as Chief Strategy Officer for Bedrock Real Estate where he oversaw several functional areas including corporate strategy, economic development and hospitality. Mark also spent three years with Accenture’s Strategy Management Consulting practice in Washington D.C., where he specialized corporate strategy, growth strategy, operating model design, and financial projects.
Mark is a graduate of Michigan State University, where he earned a bachelor’s degree in finance from the Eli Broad College of Business, a bachelor’s degree in German from the College of Arts and Letters, and a specialization in international business.