I'm Kyle Macmillan, a Toronto-based Solutions Engineer at Square. I've spent 8+ years solving real business problems with technical solutions that actually hold up.

My path started with mechanical engineering at the University of Ottawa, took a turn through Deloitte where I led multi-million dollar digital transformations as a Manager of Product Engineering & Delivery, and now has me at Square helping businesses grow. Through all of it, I've thrived in the space between strategy and execution, translating messy, complex problems into solutions that actually ship.

At Square, I partner directly with merchants and businesses to understand their goals and architect tailored solutions that drive real growth. Before that, at Deloitte, I led cross-functional teams through enterprise cloud transformations, navigating the ambiguity, stakeholder complexity, and execution demands that come with large-scale change.

My technical foundation spans full-stack development, enterprise architecture, and program delivery. I'm comfortable across the stack, from React, Python, Java, and SQL to the major cloud hyperscalers, containerization, and a long list of enterprise platforms. But the tools are just the means. What I'm really focused on is understanding the problem deeply, building the right solution, and making sure it gets delivered.

Outside of client work, I write here about what I'm learning, the bigger questions that come up along the way, and the occasional opinion I can't keep to myself.