Apptio CEO Sunny Gupta didn't have to raise more cash, since his fast-growing upstart still had money in the bank from a $14 million round last August. But the seasoned entrepreneur decided that another equity round would supercharge the business at a perfect moment in time. Because of that belief, Apptio today is announcing an oversubscribed $16.5 million venture round from existing investors like Madrona Venture Group, Greylock and Andreessen Horowitz. Led by Shasta Ventures, the financing deal brings total funding to $37.5 million.

Entrepreneurs don't always like the idea of taking on more venture money as it can dilute their personal equity positions. But Gupta said he didn't really look at it that way when investors started calling.

"Really, we believe in the bigger pie theory," said Gupta, who previously worked at iConclude, Opsware and Performant. "So, we felt like: Why don't we take on additional capital which allows us to scale our business even faster than what we would have done without having this capital. This, for us, is all about taking advantage of a big market opportunity."

The 40-year-old Gupta is a bit of a rarity in Seattle, a proven entrepreneur who is incorporating a swing-for-the-fences mentality at Apptio. He's told us before (and repeated again this week) that he wants to build the next big technology brand in the Pacific Northwest.

"We are very committed, and even more so now after this series C round, to really build a very large company in the Northwest," he said. "I've never seen a market opportunity like this, and more spectacular has been our execution against that market opportunity. So, that really gives us the conviction to run this business for a long time."

Sunny Gupta

The company, which has developed an online software system to help CIOs get a better handle on their corporate IT costs, has been on a serious growth curve this year. Gupta wouldn't disclose revenues, but gross bookings are up more than 300 percent year-over-year. Apptio now has more than 50 corporate customers, including big names such as Alaska Airlines, Blue Cross Blue Shield, BNP Paribas, Cisco, Starbucks and Volkswagen Credit.

Employee headcount also is on the rise, more than doubling so far this year to 85 people. By the end of the year, Gupta expects to be at 115 employees.

One of the reasons why Apptio is meeting with success is that chief information officers -- some with annual information technology budgets of $1 billion or more -- are looking at ways to gain insights about IT costs. Apptio not only offers a decision making engine which makes it easier for CIOs to determine how and where to cut or add costs, but Gupta said the company is expanding deeper into budgeting and forecasting for their IT departments. A benchmarking tool also allows CIOs compare across departments or industry sectors.

Apptio competes against H-P and BMC, but Gupta said that 85 to 95 percent of the deals they enter are non competitive. However, he said the competitive landscape is starting to shift.

"Certainly, the big guys -- the system management companies -- have really started to talk about it," he said. "But what we believe and what Apptio does that is different ... is that those guys are all about how the CIOs manage the technology itself. And, traditionally, they have not really helped them manage the business of technology. And that's why we think we are a new category of software which is different than what the existing guys do and we certainly believe we have a 24 month lead on any of the big guys."

Apptio's customers typically pay an annual license fee up front, with contracts typically ranging from $100,000 to more than $1 million. He said Apptio service can start delivering valuable insights about a large IT organization in a matter of weeks.

Those higher price points put Apptio in a stronger position than many software-as-service models, creating what Gupta hopes is a new type of recurring revenue model.