Cooper is an AI coworker for the insurance industry. Getting a business insured involves mountains of paperwork: filling out repetitive forms, re-typing the same information into one insurance company’s website after another, and comparing offers by hand. We’re a small team with deep insurance roots, teaching AI to do real, trusted work in a massive, overlooked industry. Backed by Lightspeed, General Catalyst, and Valor, Cooper AI is building from the ground up to modernize a $1T+ global insurance industry. We’re hiring the Founding Engineering team for a new hyper-growth AI business unit. You’ll build AI agents and AI workflows that enable unique, tailored experiences for insurance use cases
- so insurance professionals can move 10x faster and unlock major efficiency gains. Full stack engineering experience.



You’ll be coding across the stack and are comfortable in different languages and platforms. Hands-on with contemporary AI stacks (LLMs, VLMs, ASR / TTS, vector stores, orchestration, evals). You’ll map out complex customer workflows and deploy end to end custom builds. Competitive salary & equity ~ Medical, dental & vision insurance ~ Off sites, happy hours, and team building events 180K – $220K
• Offers Equity We set our salary ranges using compensation data from companies similar to our stage and size. The actual base salary will vary depending on multiple factors unique to each candidate, including location, job-related knowledge, transferable skills, work experience and our assessment of your level during the interview process. #

📌 AI Engineer (Winnipeg)
🏢 Cooper AI
📍 Winnipeg