Engineering Manager, AI

Jobgether; Canada; Remote; CAD 190,000 - 240,000; Full time

Benefits offered by this job

Stock option grant

Comprehensive medical, dental & vision

Maternity & paternity leave

Four weeks vacation (flexible timing)

Remote-first; work from anywhere in CA

Job summary

Jobgether is seeking an Engineering Manager, AI in Canada to lead an AI engineering team building production-ready features and scalable AI infrastructure within a regulated healthcare environment. You will partner with Product, Clinical, Pharmacy, and Customer Experience to shape the AI roadmap while ensuring safety and accountability.

You will guide evaluation frameworks, model management, and observability, balancing innovation with reliability.

Qualifications

• At least 3 years leading engineering teams.
• Hands-on experience shipping LLM/ML products to production.
• Knowledge of AI evaluation methodologies.
• Judgment on when AI is appropriate vs alternatives.
• Strong leadership to unblock teams and grow engineers.
• Clear communication with product and stakeholders.
• Familiarity with AI evaluation, observability, experimentation.
• Experience across frontend and backend technologies.
• Balance innovation with reliability and safety.
• Experience in regulated industries is a plus.

Responsibilities

• Lead AI engineering team delivering production-ready capabilities.
• Define and optimize AI systems and frameworks.
• Establish standards for AI quality and release criteria.
• Own production AI performance, cost, latency, observability.
• Collaborate with Clinical, Pharmacy, and Customer Experience teams.
• Partner with Product and Design to shape AI roadmap.
• Lead team planning and development ceremonies.
• Contribute to engineering and business decisions balancing trade-offs.
• Mentor and develop engineers.

Skills

Engineering leadership

LLM deployment

Cross-functional collaboration

AI evaluation methods

Observability & monitoring

Frontend & Backend experience

Strategic planning

Tools

Model management

Evaluation tooling

Prompt engineering

Observability tools

Job description

Our partner is looking for an Engineering Manager, AI based in Canada.

Lead the development of applied AI products that improve patient experiences and help healthcare teams operate more efficiently. As Engineering Manager, AI, you will guide a team building and deploying LLM-powered features and AI infrastructure in a regulated healthcare environment. You will shape the AI roadmap in partnership with Product, Clinical, Pharmacy, and Customer Experience teams, ensuring that innovation is balanced with accuracy, safety, and accountability. From evaluation frameworks and model management to production monitoring and performance optimization, you will establish the engineering practices needed to deliver reliable AI at scale. This role combines hands‑on technical expertise with people leadership and strategic decision‑making. Join a remote‑first team where your work can meaningfully expand access to digital healthcare across Canada.

Accountabilities

You will lead the AI engineering team in delivering production-ready AI capabilities while establishing the technical foundations, quality standards, and operational practices needed for safe and reliable deployment.

• Lead, develop, and grow a team of engineers building AI-powered features and platform capabilities across patient-facing and operational experiences.
• Define, build, and optimize the systems supporting AI products, including evaluation frameworks, prompt and model management, retrieval systems, guardrails, and monitoring.
• Establish standards for measuring AI quality and develop evaluation practices that enable confident, evidence-based product releases.
• Own the operational performance of AI systems in production, including model upgrades, cost and latency optimization, and observability to detect performance degradation early.
• Collaborate with Clinical, Pharmacy, and Customer Experience teams to maintain appropriate human oversight and ensure AI solutions meet clinical and regulatory expectations.
• Partner with Product and Design to identify opportunities, brainstorm new features, prioritize initiatives, and shape the AI roadmap.
• Lead team planning, ceremonies, and development processes in alignment with product priorities.
• Contribute to engineering and broader business decisions, balancing technical quality, product outcomes, operational needs, and long-term scalability.
• Foster a collaborative engineering culture through mentorship, knowledge sharing, and continuous professional development.

Requirements

You are an experienced engineering leader with a strong technical foundation in applied AI and a practical understanding of what it takes to deploy reliable machine learning systems in production.

• At least 3 years of experience as an engineering leader or engineering manager.
• Hands‑on experience taking LLM-based or machine learning-driven products from development into production, beyond prototypes or experimental projects.
• Strong understanding of AI evaluation methodologies, including how to measure output quality objectively and establish reliable release criteria.
• Sound technical judgment about when AI is an appropriate solution and when alternative approaches are more effective.
• Demonstrated leadership skills, including the ability to unblock teams, guide technical execution, and support engineers' growth.
• Strong communication skills, with the ability to explain technical concepts clearly and collaborate effectively with Product and cross‑functional stakeholders.
• Familiarity with AI evaluation, observability, and experimentation tools and practices.
• Experience working across both front‑end and back‑end technologies.
• Ability to balance innovation and delivery speed with reliability, safety, and operational performance.
• Experience in a regulated industry, such as healthcare, fintech, or insurance, is an advantage.

Benefits

• Annual compensation: CA$190,000–240,000.
• Equity through a stock option grant.
• Comprehensive medical, dental, and vision benefits.
• Maternity and paternity leave policy.
• Four weeks of vacation, including three weeks to use throughout the year and one week during the holiday period.
• Remote‑first work environment, with the flexibility to work from anywhere in Canada.
• Collaborative, high‑performing team culture.
• Opportunity to make a significant impact within an early‑stage technology company.
• Professional development opportunities and close collaboration with founders and senior leadership.
• Inclusive recruitment practices, with accommodations available at any stage of the hiring process.