Executive Leadership (Contents)

Timothy J. O’Shaughnessy was named president and CEO of Graham Holdings Company (GHC) in 2015. He joined the Company in 2014 to lead investments, acquisitions and set a new strategic direction for the Company following the sale of The Washington Post. Under his leadership, GHC has diversified into several new sectors to include manufacturing, healthcare, restaurants, and automotive.

Prior to joining Graham Holdings Company, O’Shaughnessy served as chief executive officer of LivingSocial, which he co-founded in 2007. During his tenure, the e-commerce and marketing company grew sales to nearly $2 billion. Earlier in his career, he worked at AOL as a product manager. He later moved to Revolution Health, where he rose to vice president of product development. During that time, O’Shaughnessy and three others developed a successful series of applications for Facebook. That company grew into LivingSocial, where he was CEO for seven years.

O’Shaughnessy holds a BSBA in Marketing, Operations and Information Management from Georgetown University. He is a member of the Federal City Council and serves on the Executive Committee. He has served as a board member and advisor to several private companies.

He is married to Laura Graham O’Shaughnessy, a daughter of Donald E. Graham, and lives in Washington, DC, with their three children.

Jacob (Jake) Maas is an executive vice president of Graham Holdings Company where he is a key member of the executive team leading the Company’s investment and development strategies. Maas joined the Company in October 2015 as senior vice president of planning and development. Prior to joining Graham Holdings, Maas spent 7 years at LivingSocial in a variety of leadership roles to include chief financial officer, executive vice president of operations, and head of corporate development. He helped grow the company from a small startup to a global enterprise with nearly $2 billion in sales.

Previously, Maas served as a managing director at Revolution Health Group, helping to acquire and build a portfolio of technology companies focused on consumer healthcare. Maas also worked on Capitol Hill for Senate Majority Leader Tom Daschle and served as the press secretary on his re-election campaign in 2002. Maas began his career as an investment banker at Credit Suisse First Boston in the Media and Telecom division, advising on both M&A and corporate finance transactions.

Maas earned his MBA from Harvard Business School and his undergraduate degree in economics from Stanford University, where he was an "All American athlete" on the track and cross country teams.

Andrew S. Rosen is Chairman and CEO of Kaplan, Inc., among the world’s largest, most diverse education organizations. He also serves as Executive Vice President of Graham Holdings Company (NYSE: GHC), Kaplan’s parent company.

Since he joined the company in 1992, Kaplan has transformed from an unprofitable test prep firm to a broad global educational enterprise known for its innovation in higher education, professional licensure, certifications and workforce development, international university pathway programs, English-language training, university hosting, and transnational education, while restoring its pre-eminence in test preparation. Rosen has helped pioneer much of the company’s innovation and growth, with a focus on student success and outcomes. These innovations include a focus on learning science as the foundation for all its programs, its early adoption of online instruction and competency-based learning, and its commitment to demonstrating measurable results for its students.

Over the past decade, Kaplan has expanded its relationships with universities and corporate clients, while extending its roots serving individual students.

Most recently, Mr. Rosen oversaw the transfer of Kaplan’s primarily online university to Purdue, which enabled the creation of Purdue University Global, an extension of the Purdue University System designed to serve working adults. He is the author of Change.edu: Rebooting for the New Talent Economy, which offers a prescription for restoring the pre-eminence of American higher education.

Prior to Kaplan, Rosen was Assistant Counsel at Newsweek after earlier serving as a staff attorney for The Washington Post newspaper. Before joining The Washington Post Company (now Graham Holdings Company), Rosen clerked for the Hon. Levin H. Campbell, Chief Judge, U.S. Court of Appeals for the First Circuit (Boston, MA) after graduating from Yale Law School. His bachelor’s degree is from Duke University.

Wallace R. Cooney, senior vice president, finance and chief financial officer, joined Graham Holdings Company (then The Washington Post Company) in 2001 as controller. He became the vice president, finance and chief accounting officer in 2009 and served in that role until 2017. From 1997 to 2001, he was director of financial reporting at Gannett Co., Inc. Cooney began his career with Price Waterhouse in 1985, serving three years in The Hague, The Netherlands, from 1991 to 1994 and as a senior manager from 1994 to 1997. 

Cooney graduated from Lafayette College in 1985, cum laude and Phi Beta Kappa, with a bachelor’s degree in economics. He served on the Standing Advisory Group (SAG) of the Public Company Accounting Oversight Board (PCAOB) from 2013 to 2015 and is a member of Financial Executives International (FEI), where he served on the Committee on Corporate Reporting (CCR) from 2001 to 2018. Cooney is also a member of the American Institute of Certified Public Accountants.

Sandy Stonesifer joined Graham Holdings in 2020 and became vice president and chief human resources officer in 2021. Prior to joining the Company, Stonesifer owned and operated an independent consulting practice providing organization development coaching and facilitation to leaders, leadership teams, and boards. 

Previously Stonesifer held leadership roles in the social sector and government. Most recently, she served as a political appointee at the U.S. Agency for International Development, where she led the Agency's external advisory committee comprised of major partners and stakeholders.

Stonesifer earned an MS in organization development from American University and an undergraduate degree in biomedical ethics from Brown University. She lives in Washington, DC with her husband and three young children.

Spiro Roiniotis is Vice President and Chief Technology Officer of Graham Holdings Company, leading AI and technology initiatives across the company's diverse portfolio of businesses. He stepped into the corporate CTO role in late 2025 after more than 15 years leading product and engineering teams at several of the company’s business units.

Spiro joined Graham Holdings (then The Washington Post Company) in 2009 as part of its nascent WaPo Labs group. There, he helped launch platform services and consumer-facing products before going on to lead engineering and product development at SocialCode and Decile. Across roles at Graham Holdings and at earlier companies, he has built AI-powered products, with a recent focus on applying the latest AI tools and models to meaningfully improve product development, operations, and the way teams work.

Before Graham Holdings, Spiro was Director of Technology at Folio Investing. He led the team behind the company's patented online portfolio trading platform, including its licensing and customization for international markets. He originally joined Folio Investing in 1999 as part of the core team that launched the initial platform, which was later acquired by Goldman Sachs.

Spiro holds a Bachelor of Science in Computer Science from the University of Virginia. He lives in Arlington, VA with his wife and three children.