For Sunny Gupta, the inspiration behind Apptio started with a simple question: What are you struggling with?
After selling two companies, Gupta wasn’t really looking to launch another startup. But it was that question, during a 2007 conversation with a CIO at a large financial firm, that got his entrepreneurial gears going again.
“We spend $3 billion on technology and it’s only going to grow,” the CIO told him. “We don’t know how to manage our cost base and how to demonstrate the value of our technology investments.”
Gupta set out to solve that problem with Apptio, which helped companies get a handle on their software spending and pioneered a new category called “Technology Business Management.” The Seattle-area startup went public in 2016, got acquired by Vista Equity Partners in 2019 for nearly $2 billion, and was purchased again last year by IBM in a $4.6 billion deal.
Asking good questions was key to Gupta’s startup success. Early in the Apptio journey, he put together a customer advisory board as he searched for validation.
“I kept asking: why would you buy? Why would you not buy?” Gupta recalled last week at an event in Seattle hosted by Stifel Venture Banking and Wilson Sonsini.
Apptio went on to raise more than $130 million in private funding before its successful IPO in 2016.
The company’s journey had plenty of bumps along the way, particularly in its first year trading on the public markets, when Apptio lost nearly half its market capitalization.
Gupta said the company’s ability to morph and change helped it maneuver around challenges. He also pointed its culture.
“We were really the grinders,” Gupta said. “We had a lot of grit. We persevered.”
Gupta, who started Apptio in the Bellevue, Wash., library and his home basement, said part of the motivation behind building Apptio was to do something big in his backyard.
“We wanted to build the next large software enterprise software company in the Pacific Northwest,” he said.
Apptio, which has more than 1,300 employees and 1,800 customers, is one of the region’s biggest tech success stories. And many more could follow, based on Gupta’s assessment of the Seattle market.
“The access to talent is incredible,” Gupta said, noting the presence of two of the five largest tech companies as measured by market value (Amazon and Microsoft).
Gupta, who stepped down as Apptio CEO this year and remains a strategic director at Madrona — an early backer of Apptio and his previous company iConclude — said Seattle is also a great place for startups to find their initial customers.
“People are very receptive to early concepts and ideas,” Gupta said. “I think it’s a better place to build these companies than the Bay Area.”
