Leadership Team

Keith Hoogland


In 1995, Keith took over for his father, Charlie Hoogland, as CEO. He grew Family Video to over 800 locations, becoming the 3rd largest video rental chain in North America. He strategically purchased all Family Video retail real estate which allowed Family Video to remain in business years after the closing of its competition. Always the entrepreneur, he continues to expand the company though real estate development and into other retail, food service and healthcare industries.

Passionate about giving back both locally and globally, Keith created local programs that recognized student achievements, provided turkeys and hams to those in need during the holidays and sent movies to deployed troops. He also created one of the first round it up charitable campaigns supporting Lymphoma research. With contributions totaling over $8 million dollars he established a research biobank at the University of Chicago. This research has significantly increased the effectiveness of treatment options for Lymphoma and has had positive impacts on other cancer treatments.

He received his undergraduate degree from Vanderbilt University, where he met his wife Susan. His large family is growing with 6 children and 9 grandchildren and counting.

Jon Hill


Jon is responsible for financial management, risk management, and strategic planning. He has more than 20 years of experience in Treasury, Finance, Risk Management and Accounting with a specialization in the real estate industry. He received both his undergraduate degree and MBA from Mercer University.

McLain Hoogland

President of Hoogland Restaurant Group

McLain leads our Hoogland Restaurant Group and Highland Pure Water and Ice divisions. He served in the United States Marine Corps as an Infantry Officer for over 4 years, deployed in both Afghanistan in support of Operation Enduring Freedom and Okinawa, Japan as a Weapons Platoon Commander. He received his undergraduate degree from Vanderbilt University and an MBA from Pepperdine University.

Deanna Flynn

Vice President of Marketing & Analytics

Deanna leads our Marketing and Analytics teams. With over 7 years at Highland, Deanna has led efforts to expand our customer base and marketing channels based on data centric decision making. Deanna has over 20 years experience in multiple industries and business disciplines. She received her undergraduate degree from West Virginia University and an MBA from DePaul University.

Sam Stilp

President of Legacy Commercial Property

Sam leads our Real Estate division, encompassing leasing, development, acquisition and disposition. Prior to joining Highland Ventures ten years ago, Sam developed several shopping centers for tenants including Best Buy, Verizon, Kay Jewelers, Starbucks and AT&T. Sam also worked at Northmarq, a mortgage banking firm and Julian Toft & Downey where he worked on structured finance and equity developments. Sam received his undergraduate finance degree from Marquette University and an MBA from University of Chicago, specializing in Finance.

Ben Hoogland

Vice President of Highland Ventures

Ben leads our development of new business concepts. Prior to joining Highland Ventures, Ben worked in mergers & acquisitions at Lazard Freres before moving on to venture capital at Sandbox in Chicago. He received his undergraduate degree from William & Mary and an MBA from Duke University.

Stephanie Forsberg

Director of Human Resources

Stephanie leads our Human Resources team and supports our employees across areas of the company. With over 20 years of experience, she brings her passion for our teams and ensuring they have a great experience while working for Highland Ventures and its subsidiaries. Her background includes leading all aspects of human resources across multiple industries. She received her undergraduate degree from Auburn University.

David Moss

Director of Property Management

David is the head of our property management division, where he is responsible for our portfolio of 650+ properties.  David has 15 years of commercial property management experience, managing multi-million SF retail & mixed use facilities.

Dan Powers

Director of IT

Dan oversees all vision, strategy, and execution of our IT operations. Dan has over two decades of experience building and evolving the technological infrastructure. Dan has successfully managed the rollout and execution of numerous enterprise IT initiatives that have produced exemplary results.