Community Spotlight: Taylor Kawaguchi on Trusting her Instincts, Leading with Clarity, and creating askelle on Her Own Terms

Meet Taylor Kawaguchi 

Taylor Kawaguchi is the founder of askelle, an AI-powered platform that helps mission-driven organizations simplify and streamline funding applications. Her path to building a tech company was shaped not by venture pitches or accelerators, but by lived experience, burnout, and a quiet moment of clarity during maternity leave. 

Most of Taylor’s career has been spent in the nonprofit world. She started in fund development and eventually moved into project and asset management at a large Western Canadian organization. She was often the person behind the scenes making things work, navigating complex funding systems and managing capital grants. Over time, the pace and pressure of that work began to wear on her. 

“I burned out in a senior ops role and took maternity leave,” she says. “I knew I needed a more flexible path that let me spend more time with my two-year-old daughter. That’s really what sparked the idea for askelle. The company is actually named after her, which makes it even more special to me.” 

A Founder Grounded in Real-World Insight 

As Taylor prepared to step away from her role, she had to transfer years of knowledge to her team. The most difficult part was explaining how she managed complex capital grant and contribution applications. That process revealed something larger: these systems were not built to be easily shared or sustainable. 

“While I was away, I chatted with my two directors, both with startup backgrounds, and it turns out we’re not alone. Lots of organizations run into the same issues when they’re trying to figure out funding.” 

That realization stuck. Taylor didn’t rush into building a product. She paid attention to the patterns and began imagining what it might look like to solve them in a different way. 

Values First, Technology Second 

askelle isn’t just a platform. It reflects how Taylor works and leads. She builds with care, communicates clearly, and prioritizes trust. 

“At askelle, we really focus on two things: being open about your data and making content that feels like it’s yours,” she explains. “You always get to decide how your information is used, which is super important if you’re in an industry where sensitive data or IP matters.” 

Rather than forcing organizations to adopt a generic system, askelle learns from the content they already have and helps produce proposals that feel authentic to their brand and voice. 

Pacing Growth with Intention   

In the past year, Taylor and her team have moved from early wireframes to a fully operational product. Beta 2.0 launches in August, and a public alpha is planned for 2026. These milestones represent more than just progress. They reflect her commitment to building something sustainable, thoughtful, and useful.   

“We have transformed askelle from initial wireframes and preliminary code into a fully operational product launched to the public market. This achievement reflects the dedication and vision of the askelle team, who are committed to addressing our customers’ needs.” 

One of her proudest accomplishments is building a technical foundation that allows the product to scale without compromising on privacy or integrity. It hasn’t been easy, but it’s exactly the kind of behind-the-scenes work she’s always been good at. 

Advice from Experience 

Taylor is open about what she wishes she had done differently. “Looking back, I wish I’d trusted my instincts more, especially when it came to bringing technical talent onto the team.” 

She describes staying too long with an early technical team that wasn’t aligned with askelle’s vision. It slowed progress and led to missed opportunities. “There was a mismatch between their approach and our vision, and it meant we wasted resources heading in the wrong direction.”  

Now, she leads with more confidence and encourages other founders to do the same.   

“Getting stuck in indecision—what I like to call decision paralysis—can be a real company killer. Don’t be afraid to just go for it, even if your decision turns out to be the wrong one. You’ll still walk away with valuable lessons.” 

She also reminds other women building companies not to get discouraged by what they see online. 

“In this virtual world, everyone is always sharing their latest wins or showing off their amazing progress, and it can really make you doubt your own journey. But what you don’t see is the everyday reality most founders face, dealing with messiness, setbacks, and the constant ups and downs.” 

And the best advice she’s ever received? 

“No one really knows what they are doing. We are all figuring it out as we go along. Give yourself a break to figure it out too.”