To power measurable employee engagement worldwide.

About the job - Applied AI Engineer Join the Engineering Team, where you'll help build our agentic future. 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. Ruby on Rails and Vue.js in a production SaaS codebase

• Amazon Bedrock for model inference

• AWS on EKS, provisioned with Terraform and Terragrunt across regions

• MySQL and PostgreSQL. We're mid-migration to a GitOps deployment model with Argo CD and Karpenter. It's careful system design, honest measurement, and shipping production systems that people rely on every working day. 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.

Agentic Design & Orchestration: Build agentic workflows and orchestration patterns (dynamic 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. 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. 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. Be a full participant in helping the engineering culture evolve as we grow. You hold a Bachelor's degree (or higher) in Computer Science, Statistics, Mathematics, or Engineering, or equivalent practical experience. ~3+ years of professional software engineering experience, including hands-on work with AI/ML or LLM-powered features. ~ Strong fullstack experience - Ruby on Rails (or any other backend language/framework) and Vue.js/React (or any other framework) preferred.

Working knowledge of AWS beyond the console: IAM (roles, policies, least privilege), VPC and networking basics, secrets management, and how a containerized workload gets deployed and observed. You’ve taken LLM work past a prototype at least once - you've thought about output quality, iterated on prompts against real usage, and dealt with the gap between "works in the notebook" and "works for customers." ~ You understand how to structure LLM calls for reliability: using function calling and structured outputs to ground results, testing responses systematically,



and designing for failure modes (hallucinations, latency, cost). ~ 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 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 are comfortable with agile development. ~ Side projects count.

You’ve built an eval harness that changed a decision - where the numbers told you to ship, hold, or roll back, and you listened. You’ve operated AI in production - you've been on the other side of a cost spike, a provider outage, a model deprecation, or a quality regression that only showed up under real traffic. You've built with AI coding agents and have a view on what they're valuable and bad at - we use them, and we're still figuring out the right practices.

You prototype fast, iterate quickly, and use data to change direction when the evidence says so. 100% employer-paid benefits + a Health Spending Account from day one ~ Generous vacation package to recharge and relax ~ Personal development budget to fuel your growth ~ One personal day + two volunteering days to give back ~ Beautiful downtown Toronto office for hybrid work-fully stocked with all the best snacks Compensation is thoughtfully determined based on your experience, skill set, and alignment with our internal compensation framework and internal equity. This is a net recent position for our AI Engineering Team based out of our downtown Toronto office, at King and Spadina. Our team works in the office 3x per week or as needed to promote collaboration.

Imagine being part of a team of brilliant minds, all shaping the future of workplace communication. Here at ContactMonkey, we're not just sending out traditional emails with our internal comms software; Diversity is our strength At ContactMonkey, we are building diverse products and we need a diverse team to do that. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.

AI Disclosure We use AI to take notes during our interview. Our applicant tracking system utilizes AI for workflows and hiring process efficiencies. #

📌 Staff Applied AI Engineer (Toronto)
🏢 ContactMonkey
📍 Toronto