Kyle Maskewich · Staff Content Designer
Nine years in, I work on the structure underneath complex products: information architecture, content models, and the design systems and AI that scale them. I build it with the whole team, to hold up long after launch.
I led content for Shopify's one-page checkout, lifting conversion across mobile and desktop at global scale.
I redesigned account balances for 200,000+ new investors, with fewer support calls and a higher NPS.
I built Questrade's first content design system inside Allspark: writing guidelines, a terminology glossary, and component standards, with the team to run them.
I led the content architecture for Microsoft's M365 design-system docs: the ecosystem map, the IA, the audience model, and a CMS schema precise enough to build without interpretation.
I turned account display into a content token system, built into a backend API that powers 100+ features across every Questrade product.
I defined what AI getting it wrong looks like before any copy was written, so TurboTax Canada's first AI-powered categorization earned trust. Every target confirmed at launch.
