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.
Brian Eby
President
Brian Eby
President
Brian Eby brings over 30 years of gaming and hospitality experience to his role as President of JACK Entertainment. As president, he provides strategic direction for the company and guidance to the JACK leadership team.
Previously, Eby held the position of Executive Vice President of Corporate Operations and Chief Innovation Officer, where he oversaw the corporate departments of human resources, information technology, innovation, gaming, design and construction, food and beverage, and home office administration. Before joining the JACK Entertainment team in 2014, Eby was executive vice president of operations for Warner Hospitality LLC where he was responsible for the strategic direction and performance of the company’s four tribal gaming properties and business operations, including slots, table games, technology, food and beverage, marketing, and hotel.
Angela Matthews
Executive Vice President of Operations
Angela Matthews
Executive Vice President of Operations
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.