Senior AI Systems Engineer (Automation / Agents / Data Infrastructure)
Team: Full Stack Developer
Location: Toronto, Ontario
Commitment: Full-Time
Workplace Type: onsite
Sports betting is booming, but most bettors still fly blind. Betstamp changes that. Since 2020, we've built the go-to platform for odds comparison, +EV betting discovery, and real-time bet tracking across 200+ sportsbooks, DFS, casino, and sweepstakes sites. Our tools level the playing field so every bettor, rookie to pro, has an edge.
We're a product-obsessed, data-driven startup where shipping great features beats endless meetings, and where every engineer has a direct line to user impact. If you thrive on ownership and want your code to improve someone's ROI tomorrow, you'll fit right in.
The Role
We're looking for an AI-native engineer who focuses on building systems that automate engineering work and multiply developer output using AI, tooling, and large-scale data pipelines.
What You’ll Build
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AI workflows that generate and validate code, scripts, and integrations
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Systems that automatically create and maintain sportsbook data feeds
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Developer tooling that automates debugging, testing, and deployments
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High-scale data ingestion pipelines for sportsbook markets and odds feeds
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Monitoring agents that detect failures and propose fixes automatically
What We're Looking For
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Building AI workflows, agents, or developer automation tools
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Designing systems that run large numbers of automated jobs or integrations
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Building data pipelines, scraping systems, or distributed backend infrastructure
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Experimenting with LLM orchestration or AI development tooling
This role is not focused on traditional feature development. We're looking for engineers who enjoy building automation, systems, and internal tooling that accelerate the entire engineering team. We're looking for engineers who have experience with:
You're A Great Fit If You
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Are constantly experimenting with AI tools, agents, and developer automation
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Enjoy building systems that eliminate repetitive engineering work
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Prefer building tools and infrastructure over shipping simple product features
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Move fast, prototype aggressively, and iterate quickly
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Have built things outside of work - automation tools, scrapers, AI systems, side projects
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Have 3+ years building production systems (Go / Python a plus)
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Enjoy working in an early-stage, ship-fast, own-your-stuff environment
Tech We Use
What's In It For You
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Competitive salary & raises – share in the upside you build
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Autonomy & influence – you'll make architectural calls, not just tickets.
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Gear & learning stipend – get the tools and courses that level you up
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AI-Augmentation – free reign on testing & spending on the AI tools of the future to help you excel
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World-Class betting tools – get access to our best tools that professional bettors use, for FREE
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Sports-centric culture – team watch parties, office prop pools, and the inside scoop on sharp bets.
The Process
- 45-min intro call – meet the team, swap questions.
- Lightweight take-home challenge (under 2 hours) – a real problem that reflects the type of work you'll be doing here, not a LeetCode exercise.
- Systems design interview – we'll work through a real architecture problem together, no whiteboard algorithms.
- Final interview – meet leadership, hear the vision for the role, and see if we're the right fit for each other.
- Offer → onboarding → shipping to thousands of bettors.
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