You’ll work alongside senior engineers, Product, and our Chief Product & Technology Officer (CPTO) to design, prototype, and ship AI-powered capabilities quickly
This role is hands-on and iterative, focused on building production-grade agentic workflows that improve how internal communications are curated, designed, delivered, measured, and orchestrated
This is an AI engineering role with real infrastructure ownership
You won’t be handed a platform - you’ll help build the one our AI features run on
If you like being close to both the model and the metal, this is that job
Agentic Design & Orchestration: Build agentic workflows and orchestration patterns (energetic routing, tool-using agents, feedback loops) - contributing to the design and owning the implementation of well-scoped components
Evals & Measurement: Own the eval harness for the features you ship. Build the datasets, the automated grading, and the offline regression suites that tell us whether a prompt or model change actually made things better. Raise the bar for evaluation across the team - judge design, offline and online metrics, and the judgment to know when a number is real. Turn production failures into evals that catch that class of failure next time
Infrastructure for AI: Own work with SRE and build the infrastructure your features depend on, as code. Build the deployment path for AI workloads on EKS alongside our SRE and platform engineers
Reliability, Cost & Safety: Keep our AI layer trustworthy as it grows. Instrument token spend, latency, and failure rates as first-class metrics. Design for the failure modes that matter - hallucination, timeout, rate limit, cost blowout - and make sure the system degrades gracefully instead of falling over. Respond when things behave unexpectedly in production




Prompts & Model Configuration as Code: Treat prompts as versioned, reviewable, rollback-able artifacts rather than strings someone edited in a console. Own how we move a prompt or model change from idea to production safely, and how we back it out when it turns out worse
Data Residency & Trust: We run regional deployments because our customers require it. Help make sure AI features respect those boundaries - that customer data stays in-region, model invocations are logged, and what we send to a model is what we intended to send. Think about prompt injection and PII exposure before an auditor does
Execution & Experimentation: Take a defined problem and run with it. Contribute to our quarterly AI roadmap, run experiments to benchmark model value, and iterate systematically on prompts, retrieval, and model configurations based on what the data tells you
Cross-Functional Partnership: Work closely with Product Management to turn product ideas into concrete technical work - both customer-facing features and internal workflow automation
Grow With the Team: Participate actively in design discussions and code reviews. Ask questions early, elevate blockers, and share what you learn. Contribute to documentation practices (agents, markdown, Knowledge Bases) as we figure them out together
Cultural Stewardship: Be a full participant in helping the engineering culture evolve as we grow Benefits Hybrid Work
Employee Stock Options




Personal Development Budget
Bi-weekly Lunch & Learn
Monthly Team-building Activities
Health & Dental Coverage
Bonus Opportunities
Extended Vacation Days (34 days of vacation annually, with summer Fridays, and more) This is a great fit if you’ve shipped LLM features in production, you’re comfortable when the answer involves a Terraform plan rather than a prompt tweak, and you’re ready to go deeper - with senior engineers around you to learn from You are able to work collaboratively and independently You have excellent oral and written communication skills You’ve written and applied infrastructure as code yourself. Terraform preferred - you’ve authored modules, read a plan carefully before applying it, and recovered from state that didn’t match reality. Terragrunt, Cloud Formation, or CDK experience transfers You default to AI in your own workflow. You’ve already integrated modern AI tools into how you work, and you use them to move faster rather than as a crutch You bring intellectual humility, empathy, and strong listening skills to the team You have familiarity with RAG architectures and vector stores, and an interest in multi-agent orchestration frameworks - you don’t need to have run them at scale, but you should know the landscape You can reason about what an AI feature costs to run - tokens, context size, retries, caching - and you treat that as an engineering constraint rather than someone else’s problem You prioritize a “question first, then answer” approach, thinking critically about problems before committing to a code path You hold a Bachelor’s degree (or higher) in Computer Science, Statistics, Mathematics, or Engineering, or equivalent practical experience You are

📌 Applied Artificial Intelligence Engineer (Toronto)
🏢 ContactMonkey
📍 Toronto