Senior AI Engineer
ContactMonkey•Toronto, ON
•Hybrid
About The Position
Join the Engineering Team at ContactMonkey, where you’ll help shape and build our agentic future. You’ll work closely with our Product and Engineering Teams, and our Chief Product & Technology Officer (CPTO), to turn vision into reality, partnering with a small, high-impact team 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.
Requirements
- Bachelor’s degree (or higher) in Computer Science, Statistics, Mathematics, or Engineering, or equivalent practical experience.
- 7+ years of professional software engineering experience, including 2+ years building AI/ML or data-driven systems in production SaaS environments
- Deep technical proficiency in AI systems, including handling complex subsystem interactions and dependencies.
- Experience moving LLM work past prototypes into production—thinking through eval frameworks, monitoring output quality, and iterating on prompts based on real-world performance.
- Understanding of how to structure LLM calls for reliability: using function calling to ground outputs, testing responses systematically, and designing for failure modes (hallucinations, latency, cost).
- Working knowledge of multi-agent orchestration frameworks and RAG architectures, including vector stores.
- Prioritize a "question first, then answer" approach, thinking critically about problems before committing to a code path.
- Intellectual humility, empathy, and strong listening skills.
- Ability to work collaboratively and independently.
- Comfortable with agile development.
- Excellent oral and written communication skills.
Nice To Haves
- Designed and shipped autonomous workflows where LLMs reason across multiple steps, make decisions based on tool outputs, and adapt their behavior based on feedback.
- Previous experience working within the email ecosystem or similar high-scale communication platforms.
- Proven track record of rapid prototyping, iterating quickly on features, and leveraging data to pivot when necessary.
- Act as a catalyst for new engineering principles and tools within your current organization, helping to raise the technical bar for your peers.
Responsibilities
- Contribute to the technical vision for our AI layer, driving technology adoption and research initiatives from spike to task breakdown, with a focus on core AI infrastructure to ensure our systems are robust and scalable.
- Architect and implement robust agentic workflows, multi-agent systems, intelligent system behaviors, and orchestration patterns (e.g., dynamic routing, autonomous agents, feedback loops).
- Build and execute against a 3-month strategic roadmap while refining work as you learn. Design and execute different approaches and experimentation frameworks to benchmark model value, measure success, and systematically iterate on prompts and model configurations.
- Own the reliability and scalability of AI subsystems in production, so our AI layer stays trustworthy as it grows. This includes designing and implementing comprehensive testing strategies that move beyond existing framework, focusing on systematic testing of LLM responses and failure modes.
- Collaborate closely with Product Management and the CPTO to translate business vision into concrete technical specifications and product-facing or internal workflow automation tools.
- Be active within your team and the company. Participate in meetings; volunteer to lead initiatives; escalate questions or issues when necessary. Act as a subject matter expert for complex subsystem troubleshooting, cross-org dependencies, and architectural reviews, including how to structure and maintain documentation (e.g., using agents, markdown, or external Knowledge Bases).
- Be a full participant in helping the engineering culture evolve as we grow.
Benefits
- 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
- RRSP Group Savings Plan
- Generous vacation package
- Personal development budget
- One personal day + two volunteering days
- Your Birthday off
- Five health days per year
- Beautiful downtown Toronto office for hybrid work—fully stocked with all the best snacks
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What This Job Offers
Job Type
Full-time
Career Level
Senior
