Dr. Cotsakos serves as founder, chairman and chief executive officer of Pennington Ventures, a privately held media, technology, strategic management and advisory company (1999-present).

Dr. Cotsakos serves as co-founder and chairman of Mutasian Media and Mutasian Entertainment, creative educational entertainment companies for children (2009-present).

Dr. Cotsakos serves on the board of Cengage Learning Holdings, one of the largest edtech companies in the world for students, professionals and libraries, helping students in more than 120 countries (2023-present).

Dr. Cotsakos serves as a senior advisor to New Mountain Capital, a leading private equity firm in New York. New Mountain, together with its affiliates, manages private equity, public equity and credit capital with aggregate assets under management totaling $40.0 billion+ and $40.0 billion+ in capital raised (2013-present).

Dr. Cotsakos serves on the board of Sonrava Health, a national family of health and wellness companies, with approximately 610 offices in geographically strategic areas of the U.S. Dr. Cotsakos also serves as the senior digital marketing technology advisor to the board (2014-present).

Dr. Cotsakos serves as a senior advisor to CCS Medical, the leading provider of collaborative care programs and home-delivered medical supplies for those with chronic con ions, specifically diabetes.

Dr. Cotsakos serves as chairman of the board of Boulevard Arts, an immersive arts education technology company that enables its customers to virtually experience museums, architecture and cultural sites, and public art installations from anywhere in the world (2014-present).

Dr. Cotsakos serves as a trustee of the Louis T. Graves Memorial Public Library, the public library of Kennebunkport, Maine, serving as a cultural and intellectual commons for the community, providing free and unfettered access to knowledge and life-long learning through print, electronic resources, activities, programs, and service (2023-present).

Dr. Cotsakos served as founder, chairman, chief executive officer and president of EndPlay, a leading provider of SaaS content management, engagement and monetization solutions for local broadcasters, media, entertainment and consumer packaged goods companies delivered in the cloud (2010-2014).

Dr. Cotsakos served as founder, chairman of the board, chief executive officer, and president of Mainstream Holdings, a holding company providing customizable internet technology and digital and social media, engagement and monetization solutions (2003-2009).

Dr. Cotsakos co-founded and served as co-managing general partner of ArrowPath Ventures, where he and his co-managing general partner raised over $325 million in venture capital. ArrowPath is an early-stage venture capital firm that focused on early and expansion stage companies developing highly differentiated enterprise and infrastructure technologies (1999-2003).

Dr. Cotsakos served as the original chairman of the board and chief executive officer (1998-2003) and the original president and chief executive officer (1996-1998) of E*TRADE Group. Under Dr. Cotsakos’ leadership, the company grew from a development stage start-up to a public company with a peak valuation of $16.01 billion. In addition, Fortune magazine named E*TRADE as one of the 10 most admired companies in financial services in 2002 and the company and Dr. Cotsakos received numerous industry awards and recognitions for innovation, marketing, and technology. It was also included in both the S&P 500 and the Forbes Super 500 in 2003.Dr. Cotsakos raised $13 million in private equity to help finance E*TRADE's start-up operations, led the company’s initial public offering and listed E*TRADE on the National Association of Securities Dealers Automated Quotations (NASDAQ) under the symbol EGRP in August 1996, raising an additional $53 million. In February 2001, after the company earned $1 billion in revenue, he listed E*TRADE on the New York Stock Exchange (NYSE) under the symbol ET.Dr. Cotsakos raised an additional $1.5 billion to finance E*TRADE’s growth, infrastructure, technology innovations, and leading brand-building strategy. He initiated the company’s global diversification program by acquiring 18 companies for approximately $3 billion and broadening the company's international products and services portfolio.After reporting the most profitable year in the company’s history from ongoing operations, Dr. Cotsakos stepped down from his role as chairman and chief executive officer in January 2003 to continue focusing on new venture capital opportunities and worthy causes through his portfolio management company, Pennington Ventures. Dr. Cotsakos serves as Pennington's founder, chairman and chief executive officer, which provides investment and advisory services to executive management teams, boards, venture capital funds and private equity firms.

Dr. Cotsakos served as global co-chief executive officer, president, and chief operating officer of ACNielsen, the global leader in market research, information, and analysis, with over 12,000 employees worldwide (1992-1996). Dr. Cotsakos expanded the company’s reach in Asia, Europe, and Latin America and reinvigorated its brand and market position, re-architected its technology and restored its global profitability.Dr. Cotsakos was the recipient of Dun & Bradstreet’s Chairman’s Award for Global Leadership in 1993 and the President’s Award in 1995 for his innovative leadership in developing the company’s solution-based technology and expanding the company’s profitable global strategy.

Dr. Cotsakos served 19 years with the Federal Express Corporation (NYSE-FDX), from a fledgling start-up to a market leader in transportation, information, and logistics solutions, where he held a number of senior executive positions in the U.S. and in Europe, Middle East and Africa (1973-1992).Dr. Cotsakos was instrumental in developing several of the people, service, profit, and technology initiatives that Federal Express is known and respected for today. Dr. Cotsakos received the Chief Operating Officer’s Five Star Award for Leadership and Innovation in 1984 and was instrumental in Federal Express receiving the Malcolm Baldridge National Quality Award in 1990.

Dr. Cotsakos enlisted in the military in 1967. He is a decorated Vietnam combat veteran. Dr. Cotsakos (then Sergeant Cotsakos) served in Vietnam as a fire team leader and squad leader with Bravo Company, 2nd Battalion, 501st Infantry, 101st Airborne Division (known as the Screaming Eagles). Dr. Cotsakos was honorably discharged from active military service. He received the following awards and decorations: Bronze Star Medal with V Device for Valor, Army Commendation Medal with V Device for Valor, Purple Heart for wounds received in combat, Air Medal for meritorious achievement in flight, Vietnam Service Medal, Vietnam Campaign Medal, Combat Infantryman Badge, Parachutist Badge, as well as other ribbons and citations.