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Senior AI Engineer

ContactMonkeyabout 2 months 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