While iConclude was focused on system administrators, with an automated ticketing service system, Apptio is geared toward CIOs and managers trying to keep better tabs on the expense and returns of their technology investments.

Apptio is a subscription service that builds models of customers infrastructure and then produces dashboards and reports that can be used to analyze their costs. The system can be used to monitor ongoing costs, or to model the costs of making a change such as moving from an in-house to hosted email system.

Gupta said this time around, he wants to build the company into a major presence instead of selling it early, like he did three years after starting iConclude. He's thinking it could grow to the scale of Redmond's Concur and achieve $50 million anual sales within three years.

Will investors pressure Gupta to cash out early? Gupta said no.

"Our investors, they have pretty long-term perspective,'' he said. "I've worked with all of these investors in the past. The key piece, from when we started the company, is how can we make something bigger. I feel our incentives are really well aligned."

Apptio now has about 16 employees and $7 million in funding it received last November from Madrona Venture Group, Greylock Partners, Ignition Ventures and Shasta Ventures.

Co-founder and chief technology officer, Kurt Shintaffer, also worked with Gupta at iConclude, and vice president of product management, Eric Berg, previously led product management and marketing for Microsoft's System Center products.

Advisers include Netscape and Opsware founder Marc Andreessen, who bought iConclude, and early founders of Mercury Interactive where Gupta worked earlier.

"We think it's a superstar team ready to take advantage of a pretty big market opportunity,'' he said.

Among the CIOs that Apptio has been talking with about the product is Mark Gregory, CIO of Homestreet Bank in Seattle, who was also an advisor to iConclude and has options in Apptio.

"They're really solving a tough problem that I don't think anyone has solved,'' Gregory said.

At Homestreet, Gregory could see using the service monthly to track costs against the budget.

"Personally I think he's got something here ... especially in the financial services area, it seems like there's an appetite for it."