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Sunny Gupta

Strategic Director

Sunny Gupta is the Co-founder and CEO of Apptio. He co-founded Apptio in 2007 with a customer obsession that led him to uncover significant untapped demand for pioneering a new software category (Technology Business Management or TBM) – an analytics-based business management system for CIOs. Gupta led Apptio to an IPO in September 2016  as well as its acquisition by Vista Equity Partners in January 2019 for $1.94B.  Since going private with Vista he has led 4 acquisitions, significantly expanded the customer base, expanded into international markets and  increased innovation.

As Strategic Director, Sunny advises Madrona portfolio companies at the earliest stages of innovation and, with later stage companies, as they build to scale.

Prior to founding Apptio, Sunny was EVP of Products at Opsware, responsible for all product businesses, until Opsware’s acquisition by HP in 2007. He was also the co-founder and CEO of iConclude, which pioneered the IT runbook automation market through its acquisition by Opsware. Previously, Sunny held senior leadership roles in Products, Business Development and Engineering at Mercury Interactive, Rational Software, and IBM. Sunny earned a B.S. in Computer Science from the University of South Carolina (Now Coastal Carolina University), was selected as a “Top 40 CEO Under 40”, and was recognized an Ernst & Young Entrepreneur of The Year 2012 for Pacific Northwest. Sunny was named to the prestigious Puget Sound Business Journal Power 100 list for 2020 and 2021.

Sunny joined the Gainsight Board of Directors in May 2021, and also serves as Strategic Advisory Board Member to Foster School of Business at University of Washington.