Back to jobs
tags.new

AI Architect

Toronto

Hey there! We’re ContactMonkey 👋

Our mission? To power measurable employee engagement worldwide. And we’d love for you to join us!

 

About the job - AI Architect 

ContactMonkey's platform already runs AI in production - Claude-powered template editing, a standalone ConfidenceCheck service that evaluates outgoing emails for editorial quality and link safety, Braintrust-backed evaluations, and per-organization feature gating. The next wave is bigger: grounded assistants, retrieval over customer brand and campaign history, richer agentic flows inside the composer, and data products that make sending decisions smarter.

We're forming a dedicated AI pod to own that trajectory. With the team you will be setting the technical direction for the pod, make the foundational infrastructure bets (vector store, evals, data warehouse, agent orchestration), and ship the first production systems yourself. This is an architect role in the sense that you own the shape of the thing - it is not a role where you stop writing code.

 

Your impact

  • AI platform direction: Model selection and routing, prompt and context architecture, evaluation strategy, cost and latency budgets, safety and PII handling. Decide where we go deeper with frontier models, where we fine-tune smaller ones, and where classical ML beats an LLM.
  • Retrieval and grounding infrastructure: You'll pick it, design the ingestion path (brand kits, past campaigns, template library, per-org knowledge), own the chunking/embedding/refresh strategy, and set the quality bar via evals.
  • Agent and tool-use patterns: Multi-turn tool-calling loops, deterministic fallbacks, observability, recoverable failure modes across Sidekiq and SQS, human-in-the-loop checkpoints where they matter.
  • Data engineering foundations: You'll decide whether we need a warehouse (BigQuery / Snowflake / DuckDB-on-S3/ RedShift), design the pipelines that feed both product analytics and model training/eval datasets, and make sure the lineage is clean enough that we trust what we ship. Build a foundation for the next level data analytics across the company.
  • Cloud and deployment architecture: We run on AWS (ECS, S3, SQS etc). You'll make the calls on how AI services are deployed - when a new microservice like ConfidenceCheck is the right pattern vs. embedding in the Rails monolith, how we handle GPU/accelerated inference if we ever need it, how we isolate model spend per tenant.

 

What we expect from you technically

You should be credible across all four of AI, Cloud, Data, and Fullstack - not a specialist in one with passing knowledge of the others. 

Concretely:

AI / ML

  • Built and operated LLM-backed features in production against real users.
  • Deep familiarity with at least one major provider SDK (Anthropic, OpenAI) and comfort switching between them. Understand prompt caching, structured outputs, tool use, and the tradeoffs between agent loops and pipeline-style orchestration.
  • Evals are a reflex, not an afterthought. You've run a real eval harness (Braintrust, promptfoo, in-house) against golden datasets and used it to block regressions.
  • Working knowledge of retrieval systems: embeddings, hybrid search, reranking, and where each breaks. Opinions on pgvector vs. dedicated vector DBs and when either is wrong.
  • Bonus: fine-tuning or distillation experience, classical ML for ranking/classification, prompt-injection and jailbreak threat modelling.

Cloud

  • AWS fluency at the architecture level - VPCs, IAM boundaries, secrets management, queue-based decoupling, cost control. Equally comfortable if we need to run a workload on GCP for a specific reason.
  • Container-native deployment (ECS, EKS, or equivalent). IaC experience (Terraform or CDK) - even if we aren't using it yet, you should expect to bring it in.
  • Have operated production systems under real load. You've been paged, and you've written the postmortem.

Data Engineering

  • Can design a data pipeline end-to-end: ingestion, transformation, storage, serving. Batch and streaming. Have built this in at least one real organization.
  • Comfortable with SQL and non SQL at a level that lets you reason about query plans, not just write queries. You've tuned a slow query by looking at the plan, not by guessing.
  • Opinion on when a warehouse earns its keep vs. when read replicas are enough. We're at that decision point.
  • Bonus: dbt, Airflow / Dagster / Prefect, CDC patterns, multi-tenant data partitioning at scale.

Fullstack

  • Our backend is Ruby 3.4 on Rails 7.2 with Sidekiq Pro and SQS; our frontends are Vue 3 (main app), Nuxt 4 (recipient-facing content), and a Fastify/TypeScript AI microservice. You don't need all of this on day one, but you should be a polyglot who ramps quickly.
  • Write real TypeScript. The AI-adjacent services are TS-first and that is likely to grow.
  • Understand API design past the happy path - versioning, auth modes (we run session auth for the main API and bearer tokens for integrations), rate limiting, idempotency.

 

What we bring to the table 

🏥 100% employer-paid benefits + a Health Spending Account from day one

🌎 Work from anywhere in the world for up to 4 weeks

💰 Stock option plan—own a piece of our success

💲 RRSP Group Savings Plan to plan for your future

🏝 Generous vacation package to recharge and relax

📚 Personal development budget to fuel your growth

🧖 One personal day + two volunteering days to give back

🎂 Your Birthday off—celebrate on us!

🍎 Five health days per year to stay at your best

💼 Beautiful downtown Toronto office for hybrid work—fully stocked with all the best snacks

 

Compensation & Work Details

Compensation is thoughtfully determined based on your experience, skill set, and alignment with our internal compensation framework and internal equity.

We’re always happy to answer questions about compensation throughout the hiring process.

This is a net new position based out of our downtown Toronto office, at King and Spadina. Our engineering team works primarily remote but we are looking for someone who is willing to come into the office occasionally on an as needed basis.

 

Who We Are 

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; we’re changing the way companies connect and communicate with their people. Brands like IKEA, Roku, KMPG, and countless others are using our solution to transform employee engagement.

Our all-in-one platform—featuring a drag-and-drop email builder, engagement tools, and analytics—makes it easy for businesses to create, send, and measure their internal email campaigns directly within Outlook or Gmail. This way, internal communications go from being ignored to binge-worthy, sparking more opens, clicks, and conversations.

We’ve been on an explosive growth streak over the past few years, and we’re not slowing down anytime soon. Here’s a bit of what we’re proud of:

  • Ranked by the Globe & Mail as one of Canada’s fastest-growing companies
  • Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 50™ awards for revenue growth over the past four years
  • Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 500™ as one of the fastest-growing companies in North America
  • Raised $55 million Series A financing in 2023

 

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. 

We are committed to creating an accessible experience for all candidates. If you require any accommodations or adjustments during the interview process or beyond, please inform us, and we will work with you to ensure the necessary support is in place. We are continually striving to enhance our accessibility practices and welcome any feedback or suggestions on how we can better serve candidates with accessibility.

 

AI Disclosure: 

We use AI to take notes during our interview. Applications and interviews are reviewed by our Talent Acquisition team. Our applicant tracking system utilizes AI for workflows and hiring process efficiencies.

Create a Job Alert

Interested in building your career at ContactMonkey? Get future opportunities sent straight to your email.

Apply for this job

*

indicates a required field

Resume/CV

Accepted file types: pdf, doc, docx, txt, rtf

Resume*

Accepted file types: pdf, doc, docx, txt, rtf

Select...

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in ContactMonkey’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Select...
Select...
Race & Ethnicity Definitions

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

Select...

Voluntary Self-Identification of Disability

Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 04/30/2026

Why are you being asked to complete this form?

We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.

Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.

How do you know if you have a disability?

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:

  • Alcohol or other substance use disorder (not currently using drugs illegally)
  • Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
  • Blind or low vision
  • Cancer (past or present)
  • Cardiovascular or heart disease
  • Celiac disease
  • Cerebral palsy
  • Deaf or serious difficulty hearing
  • Diabetes
  • Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
  • Epilepsy or other seizure disorder
  • Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
  • Intellectual or developmental disability
  • Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
  • Missing limbs or partially missing limbs
  • Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
  • Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
  • Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
  • Partial or complete paralysis (any cause)
  • Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
  • Short stature (dwarfism)
  • Traumatic brain injury
Select...

PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.