Senior AI Systems Engineer (Automation / Agents / Data Infrastructure)

Posted 5 Hours Ago
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Toronto, ON, CAN
In-Office
Senior level
Sports
The Role
Build AI-native automation systems, developer tooling, and high-scale data ingestion for sportsbook odds and market feeds. Create AI workflows/agents that generate and validate code, maintain data feeds, automate debugging/testing/deployments, and monitor failures with automated remediation. Focus on internal automation, LLM orchestration, and distributed backend pipelines to accelerate the engineering team.
Summary Generated by Built In
About Us:

Betstamp is the future of sports betting. We were founded in 2020 to make sports betting easy and accessible to everyone, while also improving your odds of winning your bets. Our team is dedicated to creating the best user experience possible while educating the public about sports betting.

How Betstamp Works:

We help develop winning bettors with tools, tracking, promotions, and analysis!

With 200+ sportsbook, DFS, casino & social sweepstakes sites integrated into our products, Betstamp is your one-stop for everything sports betting and advantage play. Betstamp is built by a team of winning bettors looking to help you enhance your long-term success. Whether you're a sharp, professional winning bettor or just getting started, Betstamp offers the tools and resources you need to optimize your betting strategy, increase your profits, and identify betting trends.  

Our products & features include: 
- Professional +EV Betting Screen - Quickly identify market outliers, arbitrage opportunities, and the best bets across multiple sportsbooks.
- Free Sports Betting Odds Comparison – Compare real-time betting odds & get the best price across major sportsbooks, daily fantasy sports (DFS) providers and sweepstakes sports
- Player Props Research Tool – Find and compare player prop odds for all your favourite betting sports and sports leagues
- Bet Tracking - Seamlessly input & track your bets in real-time for FREE and receive notifications when your bets win
- Betting Insights & Analysis – Use our sports betting software to analyze your betting history for actionable insights and improvements.
- Betting Community – Connect with friends, receive updates & tips from their bets, and engage with the betting community
- Betting Promotions - Stay on top of the latest promotions from betting and casino sites to maximize your dollars on Day 1!

Join the Betstamp community TODAY and unlock your edge!

Career Opportunities & Culture:

Learn more about our company at https://betstamp.com/careers!

Why Betstamp?

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

  • AI workflows that generate and validate code, scripts, and integrations

  • Systems that automatically create and maintain sportsbook data feeds

  • Developer tooling that automates debugging, testing, and deployments

  • High-scale data ingestion pipelines for sportsbook markets and odds feeds

  • Monitoring agents that detect failures and propose fixes automatically

What We're Looking For

    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:

  • Building AI workflows, agents, or developer automation tools

  • Designing systems that run large numbers of automated jobs or integrations

  • Building data pipelines, scraping systems, or distributed backend infrastructure

  • Experimenting with LLM orchestration or AI development tooling

  • You've built meaningful systems yourself (side projects, automation tools, internal platforms, or AI agents), not just shipped features inside large companies.

You're A Great Fit If You

  • Are constantly experimenting with AI tools, agents, and developer automation

  • Enjoy building systems that eliminate repetitive engineering work

  • Prefer building tools and infrastructure over shipping simple product features

  • Move fast, prototype aggressively, and iterate quickly

  • Have built things outside of work - automation tools, scrapers, AI systems, side projects

  • Have 3+ years building production systems (Go / Python a plus)

  • Enjoy working in an early-stage, ship-fast, own-your-stuff environment

Tech We Use

    Our current stack includes Go, Python, TypeScript, Postgres, ClickHouse, AWS, and LLM tooling. We care far more about systems thinking and building leverage through automation than experience with any specific language.

What's In It For You

  • Competitive salary & raises – share in the upside you build

  • Autonomy & influence – you'll make architectural calls, not just tickets.

  • Gear & learning stipend – get the tools and courses that level you up

  • AI-Augmentation – free reign on testing & spending on the AI tools of the future to help you excel

  • World-Class betting tools – get access to our best tools that professional bettors use, for FREE

  • 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.

We are a team of experienced developers writing exciting new features for Betstamp every day. If you’re looking for an opportunity to have increased responsibility, design decisions, and manage projects from start to finish, Betstamp is a good fit for you.
 
We care more about the ability to learn and deliver than ticking every box—if you’re close, apply!
 
Plan to start in April 2026, but we’ll flex for the right person.
 
The engineers who thrive here are constantly experimenting with AI tools and building systems that eliminate manual work.

Skills Required

  • 3+ years building production systems
  • Experience building AI workflows, agents, or developer automation tools
  • Experience designing systems that run large numbers of automated jobs or integrations
  • Experience building data pipelines, scraping systems, or distributed backend infrastructure
  • Experience experimenting with LLM orchestration or AI development tooling
  • Built meaningful systems yourself (side projects, automation tools, internal platforms, or AI agents)
  • Experience with Go or Python (a plus)
  • Comfort working in an early-stage, ship-fast startup environment
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The Company
HQ: Toronto, ON
20 Employees
Year Founded: 2020

What We Do

betstamp is a mobile and web based platform in the sports betting space, built for people looking to take sports betting seriously. betstamp solves the problems serious sports bettors face on a daily basis by providing them with information and tools they need to succeed. betstamp was founded and built in-house by people who bet on sports every day.

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