Kyle Maskewich · Staff Content Designer
I solve problems with systems.
Information architecture, content models, design systems, and the AI that scales them.
Work
Content strategy and architecture
Content at scale
How I work
Four ways I keep complex products clear as they scale.
- I model the system before I write
- I scale through structure, not style guides
- I get the whole room to the same words
- I build it to run without me
I treat content as architecture. Before I write, I map how the pieces connect, then design the structure that keeps them clear as the product grows. Style guides drift; systems hold. So I build shared language the whole room can use, and I make the work run without me. The real test of a system is whether it survives after you leave.
Background
I came to product design from translation and advertising, in Toronto and Paris, where I learned that clarity is a structure problem with words on top. Over the last nine years I've built that into a content-systems practice: information architecture, content models, design systems, and the token, API, and AI logic that scale them. I've worked in-house and as a consultant, from founding a content practice to leading content for the world's highest-converting checkout.
Intuit
Staff Content Designer
Aug 2025 — Now · Toronto
I lead content for CRA tax compliance at TurboTax Canada: consultation with tax analysts, a change process the team runs, and AI skills authoring. Zero compliance incidents.
Microsoft
Staff Content Designer
Jan — Jul 2025 · Toronto
Built the content system and CMS behind CxD's design-system documentation for Teams, SharePoint, and OneDrive: nested IA, a token taxonomy, and writing-instruction frameworks.
Questrade
Principal Content Designer
2023 — 2024 · Toronto
A one-year consulting engagement. Shipped Allspark, Questrade's first content design system, and a token-based account API reused across 100+ features.
Shopify
Senior Content Designer
2021 — 2023 · Toronto
Led content for the one-page checkout, the world's highest-converting checkout: mobile conversion +91%, desktop +56%.
Questrade
Principal UX Writer
2017 — 2021 · Toronto
Founded Questrade's content design practice and scaled the team from one to six. Sole UX writer for QuestMobile and every investing product.
Agencies & freelance
Copywriter & Translator
2010 — 2017 · Toronto · Paris
Translation, advertising, and brand strategy across Toronto and Paris. Carrying exact meaning across languages became how I think about content systems.
References
“Kyle was instrumental in building and launching Shopify's one-page checkout. His strategic insights and ability to simplify complex problem spaces allowed us to tackle challenges efficiently.”
“Kyle consistently develops effective strategies that align with business goals. His structured approach to information architecture made our content not only well-organized but highly accessible.”
“Kyle's candid and inquisitive nature makes him an invaluable collaborator. He takes full ownership of projects, diving deep into the research and asking the critical questions others might miss.”
“Kyle has an amazing ability to identify where content design can make the biggest impact. His systemic solutions empowered our design teams to deliver high-quality work while meeting deadlines.”
“Kyle is a great mentor and leader who brings fresh ideas and challenges conventional thinking. His proactive approach has been instrumental in fostering a culture of innovation.”
“Kyle's mentorship has been transformative, deepening my understanding of content strategy and design systems. His ability to break down complex concepts makes learning seamless.”
About
I'm a content and design-systems architect. I turn content into systems that keep complex products clear as they scale.
I work in English and French. I lived and worked in France. That cross-market lens is how I build content systems that hold up internationally.
- Languages
- English · French
- Based
- Toronto, Canada · open to relocating internationally
- Citizenship
- UK & Canada (dual)
- Level
- Staff / Principal
- Focus
- Content systems · IA · design systems · applied AI
Contact
Open to Staff and Principal roles
Let's build something good.
UK and Canadian citizen · open to relocating internationally.
