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Board Members

Sunny Gupta

Co-Founder and CEO, Apptio

Sunny is the co-founder and CEO of Apptio, responsible for company vision, strategic direction, planning, and execution. Sunny's enterprise software career spans more than 20 years with roles in general management, strategic marketing, product management, and business development. Before founding Apptio, he was Executive VP of Products at Opsware and was responsible for all of Opsware product businesses up to its acquisition by HP for over $1.6 billion. Sunny holds a bachelor’s degree in computer science from the University of South Carolina.

Tom Bogan

Chairman of the Board and CEO, Adaptive Insights

Tom joined Apptio’s Board of Directors in November 2007. He currently serves as Chairman of the Board and sits on the Audit Committee as well as the Compensation Committee. As CEO at Adaptive Insights, Tom has a deep passion for helping high-growth SaaS companies reach their potential. Prior to CEO, he was an investor and board member of several highly successful software companies including Citrix Systems and Acquia. Previously, Tom was a partner at Greylock Partners where he focused on enterprise software investments. He was also president and COO at Rational Software until its acquisition by IBM. Before Rational, Tom served as CEO at Avatar Technologies and Pacific Data. Tom holds a bachelor’s degree in accounting from Stonehill College in Easton, Massachusetts, where he also serves as a trustee.

Peter Klein

Former CFO of Microsoft

Peter joined Apptio’s Board of Directors in November 2013, where he serves as Chairman of the Audit Committee. Most recently, Peter served as the CFO of Microsoft from November 2009 until May 2013. Previously, he spent 13 years in corporate finance at McCaw Cellular Communications, Orca Bay Capital Group, Asta Networks, and While at, he helped lead the company through a successful IPO and acquisition. Peter holds a bachelor’s degree from Yale University and a MBA from the University of Washington.

John McAdam

Former CEO of F5 Networks

John has served on Apptio’s Board of Directors since February 2013. He currently leads the Compensation Committee and is a member of the Nominating and Corporate Governance Committee. During his tenure at F5, he grew the company's annual revenue from $108.6 million to more than $1 billion. Under John’s leadership, F5 was added to the S&P 500—one of the world's most widely followed stock market indices. Fortune Magazine named F5 to its 2011 list of 100 Fastest Growing Companies worldwide and in 2010, included F5 among the top "Technology Stocks for the Next Ten Years." In addition to Apptio, John now serves on the boards of F5, Tableau Software, and Nutanix. John received his bachelor’s degree in Computer Science from the University of Glasgow, Scotland.

Matt McIlwain

Managing Director, Madrona Venture Group

Matt joined Apptio’s Board of Directors in November 2007, presently serving as Chairman of the Nominating and Corporate governance committee. He is also a board member of the Washington Technology Industry Association and the Villa Academy, and serves on Washington State Attorney General Rob McKenna's Technology Advisory Board and the advisory board of Families Northwest. In his role as Managing Director at Madrona, he focuses on a broad range of software-driven companies and has previously been on the board of many successfully companies including iConclude (acquired by Opsware), Performant (acquired by Mercury Interactive), World Wide Packets (acquired by Ciena), and Isilon (acquired by EMC). Matt is a graduate of Dartmouth College, holds an MBA from Harvard Business School, and a master’s degree in Public Policy from Harvard's Kennedy School of Government.

Rebecca Jacoby

Former CIO and SVP of Operations, Cisco

As Cisco’s head of global operations, Jacoby was responsible for driving profitable growth and enabling operational excellence. In this role, she also oversaw various functions including IT, supply chain, security and trust, global procurement, and renewals. Previously, Jacoby served as Cisco’s CIO where she made the Cisco IT organization a strategic business partner, producing significant business value in the form of financial performance, customer satisfaction and loyalty, market share, and productivity. Her strong commitment to operational excellence, innovative approach to business problems, and aptitude for partnering cross-functionally reshaped and elevated the role of IT at Cisco, resulting in great synergies of IT and Engineering through a history of Cisco on Cisco deployments. In 2009, Jacoby was appointed as a strategic advisor to the Apptio’s Board before accepting a formal board seat in 2018. She was a founding member of the nonprofit TBM Council and also serves on the Board of Directors for S&P Global (NYSE: SPGI), a publicly traded financial and analytics company.

Rajeev Singh

CEO, Accolade

Rajeev joined Apptio’s Board of Directors in September 2010 and is a member of the Audit Committee. He currently serves as the CEO of Accolade, an on-demand healthcare concierge for employers, health plans, and health systems. Prior to that, he co-founded the expense management firm Concur, which is the eighth-largest SaaS company in the world. There, Rajeev served in various roles, including the Executive Vice President of Sales, Marketing & Services. Previously, he held roles in engineering project management at Ford Motor Company and General Motors Corporation. Rajeev received his bachelor’s degree in engineering from Western Michigan University.

Kathleen Philips

CFO, Zillow Group

Kathleen joined Apptio’s Board of Directors in May 2017. She is a member of both the Compensation Committee and the Audit Committee. As CFO of Zillow, Kathleen oversees finance, treasury, and accounting as well as legal operations and corporate development for Zillow Group and its portfolio of brands. She can speak to Zillow Group’s financial news and corporate strategy. Previously, Kathleen served as general counsel of Hotwire, Stubhub, Flip Video camera maker Pure Digital Technologies, and FanSnap. She received her juris doctor with honors from the University of Chicago Law School and her bachelor’s degree in political science with distinction from the University of California, Berkeley.