OEN NewsPortland at the Core: Stiira’s Specialized Leave Management Solution
Calvin Gower describes himself as “Portland born and raised,” a fact that has influenced his education, work and personal interests. After earning a degree at Portland State University, Gower launched his career in advertising and marketing. One of his early roles was at a human resources outsourcing company, where Gower was a part of scaling a boutique organization to a national brand. He then shifted into the e-learning space, revamping the company’s legacy training workshops into a virtual education program.
That experience introduced Gower to product management, where he found his passion for building innovative solutions to solve complex problems. Just before the COVID-19 pandemic, the company had launched leave administration services, an offering that exploded in popularity once the entire U.S. workforce became fully aware of protected leave, a previously unforeseen benefit to most employees. COVID also amplified the rapidly evolving regulation landscape, with a remote-distributed workforce that introduced employers to the complicated web of multi-state compliance. In the new frontier of increased leave requests and intersecting legal requirements, Gower saw a budding opportunity.
“I was overseeing our development roadmap and marketing strategy for the internal solution we were building at the time,” he explains. “It started as a sort of Swiss Army Knife application to support a few different HR services we offered, but the huge opportunity in leave management made it clear we should fine tune a specialized software to address what the market really needed.”
Stiira was born from necessity, Gower says. The team incubated the product for a few years and officially spun off into a separate technology company, introducing their leave management software to the market in early 2023. When Gower and his team researched the existing market, there were just a few legacy players that came with a price tag out of reach for 70% of the market. Stiira was designed to adapt to the new world of work, with robust functionality at an affordable cost. “We developed the first specialized third-party administrator solution for leave management, which in turn, addresses both the insourcing and outsourcing needs in the market,” Gower says.
Gower says Stiira is a Portland company through and through. All of the founding team members met here to bring the vision to life, and Portland’s startup culture is infused into the DNA of the company. “When people think of Portland, it’s usually the Nikes and Intels that come to mind, but we’re proud to be part of a new wave of innovative, emerging tech companies starting their journey in this city,” Gower says. Stiira was recently named the 2025 Angel Oregon Technology investment winner, a sign of the company’s fast expansion.
“This has been our biggest growth year so far,” Gower says. “We have really exciting new features coming down the pipeline in 2026.”
Those new features are set to differentiate Stiira further and position the startup to compete with those legacy systems that have been in the market for over a decade. As they aim to target more enterprise-level customers, Gower says the Stiira team is also growing.
The community feel of the team has been important to Stiira’s evolution. Even as Stiira’s presence grows nationally, Gower says their roots remain in Portland. The work/life balance focus, creative culture, and space to recharge in the nearby outdoors have been integral to Stiira’s journey.
“You have to be a little crazy to take on the mission of starting a technology company,” Gower says. “Which is why it’s so important to separate work and life and connect with your support system. I place a lot of value in that.”
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