Sunny Gupta

Strategic Director

Sunny Gupta

Sunny Gupta

Strategic Director

Sunny is the co-founder and CEO of Apptio.

Journey to Madrona

Sunny 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. Sunny led Apptio to an IPO in September 2016 and to its acquisition by Vista Equity Partners in January 2019 for $1.94B. Since going private with Vista, he has led four acquisitions, significantly expanded the customer base, expanded into international markets, and increased innovation.

Prior to founding Apptio, Sunny was EVP of products at Opsware. He was responsible for all product businesses until HP acquired Opsware 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.

Lessons learned

  1. Unwavering commitment to a customer – listen, learn, and have the ability to change and morph based on customer feedback.
  2. Continuously focus on things that are breaking and not working well.
  3. Focus and reward on delivering results vs. efforts.

When he’s not in the office…

Sunny loves watching the Seattle Seahawks, riding his Peloton and keeping fit, and traveling and spending time with his two kids and wife.


Sunny earned a bachelor’s in computer science from the University of South Carolina (Now Coastal Carolina University). He was named a “Top 40 CEO Under 40″ and was recognized as an Ernst & Young Entrepreneur of The Year 2012 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, joined the board of Securonix in May of 2022, and serves as Strategic Advisory Board Member to the Foster School of Business at the University of Washington and Gupta College of Science at Coastal Carolina University.

Sunny on Madrona

"I have worked with Madrona and specifically Matt McIlwain since 2003, and it has been an amazing journey. Madrona was there with me through two of my startups from day 1, helping source team, early customers, participating in customer interviews, helping raise capital, helping us decide to go public. I called Matt every week, and he coached me and helped through every step of the way — I truly felt like I got unconditional love and support to help me achieve my potential with Apptio."