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Senior AI Engineer

ContactMonkey7 days ago
Toronto
Senior Level
Full-Time

Top Benefits

Hybrid Work
Employee Stock Options
Personal Development Budget

About the role

  • Join the Engineering Team, 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
  • Architectural Ownership: Lead the technical vision for our AI layer, driving technology adoption and research initiatives from spike to task breakdown
  • Agentic Design: Move beyond simple features to architect and implement robust agentic workflows and intelligent system behaviors
  • Strategic Execution: Operate with autonomy by building and executing against a 3-month strategic roadmap while refining work as you learn
  • Production Ownership: Own the reliability and scalability of AI subsystems in production, so our AI layer stays trustworthy as it grows
  • Cross-Functional Partnership: Collaborate closely with Product Management and the CPTO to translate business vision into concrete technical specifications
  • Lead by Example: 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
  • 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)- You have working knowledge of multi-agent orchestration frameworks and RAG architectures, including vector stores
  • You possess deep technical proficiency in AI systems, including handling complex subsystem interactions and dependencies
  • You prioritize a “question first, then answer” approach, thinking critically about problems before committing to a code path
  • You are comfortable with agile development
  • You have excellent oral and written communication skills
  • You are able to work collaboratively and independently
  • You understand how to structure LLM calls for reliability: using function calling to ground outputs, testing responses systematically, and designing for failure modes (hallucinations, latency, cost)
  • You’ve moved LLM work past prototypes into production—thinking through eval frameworks, monitoring output quality, and iterating on prompts based on real-world performance
  • You bring intellectual humility, empathy, and strong listening skills to the team; you lead by example
  • You hold a 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
  • You have designed and shipped autonomous workflows where LLMs reason across multiple steps, make decisions based on tool outputs, and adapt their behavior based on feedback
  • You have previous experience working within the email ecosystem or similar high-scale communication platforms
  • You have a proven track record of rapid prototyping, iterating quickly on features, and leveraging data to pivot when necessary
  • You act as a catalyst for new engineering principles and tools within your current organization, helping to raise the technical bar for your peers

About ContactMonkey

Technology, Information and Internet
51-200

ContactMonkey is an internal communications company that helps businesses boost growth and productivity via their internal communications. With our powerful internal communications software, businesses can create, send, and track HTML email within Outlook or Gmail.

Trusted daily by over 100,000 users, 1,200 Internal Comms teams, join Amazon, Expedia, Oracle, and see what happens after you hit send.

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