OEN News2025 Angel Oregon Technology Investment Announced
Oregon Entrepreneurs Network (OEN) announced the investment recipient of the Angel Oregon Tech (AOTech) 2025 fund at an announcement mixer hosted at the Mission Theater on Monday, August 18, 2025.
Stiira, an easy-to-use leave management software solution, streamlines the employee leave process which is cumbersome, ever changing and usually managed via spreadsheets. Stiira received the $145,000 AOTech investment by showing impressive traction and year over year growth as a second year AOTech participant. The company’s specialized software system simplifies the leave management process, improving efficiency and reducing stress for administrators and employees alike. CEO and Founder, Calvin Gower along with Casey Rillahan, VP of Sales and Cofounder, presented the company alongside finalists Chandler Schaak from Hindsight VIP, Denise Ker Waldron from Life2Launch, Austin Buell and Jamie McGaw from Topsail, and Shannon Smith from Yak.
“We’re thrilled to have the AOTech family joining us on our journey,” said co-founder and CEO Calvin Gower. “This investment will be a key piece to our next stretch of growth.”
“This recognition validates both our technology and the urgent problem we’re solving,” said co-founder and VP of Sales Casey Rillahan. “And give us more momentum to deliver value to customers and scale Stiira’s impact.”
In a surprise announcement at the end of the mixer, OEN announced that Yak, a software platform that streamlines the full audit lifecycle saving auditors up to 30% of their time, would be receiving a $55,000 investment from the angel syndicate.
After a successful and unplanned AOTech investment last year, the OEN team remained committed to raising three Angel Oregon investments this year – food, technology and life sciences. This allowed OEN to raise investment from both institutional and individual angel investors, resulting in a larger investment than was deployed 2024.
This year’s AOTech angel fund is made up of investments from a dozen local investors. Investors in the program first selected 10 companies to screen after seeing 19 companies pitch that initially applied for the investment. The angel investors conducted intense due diligence on 5 finalists and selected a winner in a private vote, the results of which were revealed at the mixer. Attendees included entrepreneurs, investors and venture capital firms, universities, government agencies, service providers, and nonprofits, representing a cross-section of the Oregon and Southwest Washington technology sector.
“There were over 50 companies that went through AOTech over the past two cohorts and the innovation we are seeing across the state is impressive,” said Cara Turano, President and Executive Director of OEN. “The caliber of this year’s finalists sparked a lot of debate and inspiration among the angels. Kudos to the Stiira team on receiving this investment and congratulations to all the companies who participated. We cannot wait to see how you continue to grow your businesses.”
Oregon Entrepreneurs Network (OEN) is a 501(c)3 nonprofit organization dedicated to helping entrepreneurs start up and scale up. The organization hosts a mix of sector-specific Angel Oregon entrepreneur education and angel investment programs each year, including Angel Oregon Life & Bioscience (AOBIO), Oregon Tech (AOTech) and Oregon Angel Food (OregonAF), as well as the annual OEN Entrepreneurship Awards. Learn more at www.oen.org.
