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Fresh off Westside Pitch win, startup inks big partnership


Casey Rillahan Stiira
Casey Rillahan and two other Trupp HR workers developed Stiira to meet a growing set of needs.
Stiira

Portland startup Stiira is building software to help companies manage the myriad of regulations around paid and unpaid employee leave.

To that end, it’s recently inked a partnership with a large HR technology provider that will get the tool into more hands.

This month, Stiira announced it's partnering with Charlotte, N.C.-based Isolved to integrate the startup’s tool into the Isolved human capital management platform People Cloud.

The move is part of Stiira’s go-to-market strategy that keys into two kinds of customers, said Casey Rillahan, co-founder and vice president of sales. One set of customers is internal company HR teams that need a tool to track and manage employee leave.

The other is companies like Isolved that provide platforms that employers and HR outsourcing companies use to track this information.

The partnership comes just more than a month after Stiira won the Seed Stage pitch competition at the West Side Pitch event. The company landed a $50,000 investment. To date, the company has raised $400,000, mostly from friends and family, said Rillahan.

Stiira launched in February 2023 after incubating for two years within Portland HR services company Trupp HR. Rillahan, CEO Calvin Gower and Software Development Manager David Karstens were all leaders at Trupp.

Calvin Gower Stiira
Calvin Gower is co-founder and CEO of Stiira.
Stiira

The Stiira product started when the team, while still at Trupp, sought a product to manage employee leave but couldn’t find exactly what they wanted, Rillahan said. The need kicked into high gear once the pandemic hit and different mandatory state and federal leave options were introduced for almost every company and employee nationwide, said Rillahan.

“As soon as that happened, our phones rang off the hook,” he said. “I signed up 50 clients and $600,000 in (annual recurring revenue) in two years.”

But, the technology they were using wasn’t keeping up. And in true entrepreneurial fashion, the team at Trupp looked to build something better.

“We spent two and a half years incubating with (Trupp’s) leave specialists and software developers,” said Rillahan, before the startup spun out. “We still have a strategic alliance. They use our tool to support clients.”

David Karstens
David Karstens is co-founder and software development manager at Stiira.
Stiira

The team is still rolling out requested features for the tool, but already has 140 companies and 6,500 users nationwide. In Oregon, public sector customers have adopted it as the state’s paid leave requirements have evolved.

Stiira plans to add two workers to its full-time team of four in January 2025. It's balancing bootstrapping with fundraising, with an acquisition serving as the expected exit in the next five to seven years.

“The great thing we find is it could be an acquisition from a (human capital management) company and they take our tool and stick their name on it,” he said.

Stiira is the latest Portland tech company to launch based on meeting the need for regulatory compliance. One of the region’s largest software companies, Lake Oswego-based Navex, has built a huge business in the government, risk and compliance market. RadarFirst, which, like Stiira spun-out of an existing Portland company, has found success with software to manage data breaches and incident response compliance.

And business at digital archiving company Smarsh is also driven by compliance for its highly regulated customers.


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