Since 2005, Dennis has served as CEO of Carnegie Learning, Inc. In 2011, Dennis led the sale of Carnegie Leaning to Apollo Education Group. Before joining Carnegie Learning, Dennis was the Founder and Managing Partner of Lycos Ventures. In that capacity he served on the Board of Directors of Carnegie Learning, as well as several other portfolio companies. Dennis also served as Vice President of Mergers and Acquisitions of Lycos, Inc. Prior to joining Lycos, he was President, C.O.O. and Director of WiseWire, an internet software company. As President, Dennis negotiated the sale of WiseWire purchased by Lycos in 1998.

Earlier in his career, he worked as Managing Partner of Grove Press and at Simon & Schuster as Director of Sales and Marketing. He is also the Founder of Pittsburgh Arts & Lectures, Inc., a non-profit that continues to be a vibrant part of the Western Pennsylvania cultural scene since its founding in 1990.

In 2013, Dennis was awarded the Outstanding Entrepreneur by the Pittsburgh Venture Capital Association. Dennis lives with his wife Nancy in Sewickley, Pennsylvania, and they have three sons.