Jordan Chalupka is a Founding Product Engineer with a decade of hands-on experience building simple, scalable, and high-performance systems across startups and fast-moving product teams. He has shifted between technical leadership and founding roles—most recently at Rove after stints as Technical Lead at Boosted and Co-Founder of InsurOS—bringing product-minded engineering to early-stage companies. His background spans backend and full-stack work at Float and Amazon, plus practical machine learning deployment experience from a PagerDuty internship, demonstrating an ability to take models and services into production. Based in Toronto, he pairs an engineer’s rigor (B.Eng. in Software Engineering with a Statistics minor) with sailor-like focus and an appetite for writing, often favoring elegant, maintainable solutions over complexity.
11 years of coding experience
8 years of employment as a software developer
Bachelor’s Degree, Software Engineering with Minor in Statistics, Bachelor’s Degree, Software Engineering with Minor in Statistics at University of Guelph
Twenty fork :) -- Meet our AI-powered Insurance CRM that automates your workflows and eliminates manual tasks, so you can focus on serving your clients.
Contributions:14 reviews, 70 PRs, 79 pushes in 1 month
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