Founding AI Engineer in Winnipeg

Founding AI Engineer in Winnipeg

Winnipeg Full-Time On-site
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Who we are: 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. Cooper does that busywork automatically, right inside the tools people already use, so brokers and their teams can focus on advising clients instead of pushing paper. 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. About the role: 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. This is a high-velocity, high-impact role that will revolutionize the $1T+ global insurance market. About you: Full stack engineering experience. You’ll be coding across the stack and are comfortable in different languages and platforms.

Hands-on with modern AI stacks (LLMs, VLMs, ASR / TTS, vector stores, orchestration, evals). You’re pragmatic about trade-offs across latency, cost, reliability and safety.

Thrive in challenging situations. You’ll map out complex customer workflows and deploy end to end custom builds.

Strong communication skills. You’ll partner with Product, GTM, Design and Marketing teams, as well as directly interface with end users.

High velocity and ownership in an ambiguous environment. We’re moving exceptionally fast in a space that hasn’t been innovated before.

Benefits: Competitive salary & equity

Medical, dental & vision insurance

Monthly wellness stipend

401k with company match

Unlimited PTO

Company sponsored lunch 5x per week

Off sites, happy hours, and team building events

Compensation

$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.

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Contact Details:

Cooper AI Recruitment Team