Managing Director of Technology

Team: IT

Location: US

Commitment: Full-time

Workplace Type: remote

Accountabilities:

• Lead technical delivery for enterprise clients, serving as the senior technical authority on major engagements, evaluating feasibility, defining architecture, and ensuring solutions are successfully delivered.
• Develop scalable delivery systems and processes, including discovery frameworks, reference architectures, deployment templates, evaluation practices, staffing models, and repeatable approaches that enable multiple engagements to operate effectively.
• Hire, lead, and develop the engineering organization, setting technical standards, managing the talent pipeline, providing architecture guidance and code review, and helping engineers grow through direct and constructive feedback.
• Own platform and infrastructure direction, making decisions around build versus buy, tooling, deployment, security, and architectural priorities while partnering with engineering leadership on day-to-day execution.
• Shape AI technology strategy through hands-on experience with LLM orchestration, RAG, agents, evaluation, fine-tuning, and other emerging technologies, prioritizing technical investments based on practical client value.
• Partner closely with senior leadership on business and technical strategy while maintaining ownership of technical execution, engineering capability, and the platform.
• Engage directly with client executives and technical stakeholders, translating complex technical trade-offs into clear recommendations and decisions.
• Contribute hands-on when necessary, helping resolve production issues, unblock teams, and maintain technical depth across critical projects.

Requirements:

• Demonstrated experience building and deploying AI/ML systems in production environments that are actively used and relied upon, rather than prototypes or demonstrations alone.
• Experience hiring and leading a technical team of at least five people, with a track record of navigating organizational growth and improving team effectiveness.
• Strong ability to communicate technical concepts, trade-offs, and architecture decisions to non-technical executives and senior stakeholders in high-stakes environments.
• Deep, hands-on understanding of AI architecture, with practical experience across areas such as LLM orchestration, RAG, agents, evaluation, and fine-tuning.
• A builder-first mindset and willingness to engage directly with technical challenges, production issues, and team obstacles rather than relying solely on delegation.
• Strong knowledge of cloud infrastructure and modern engineering practices, with the technical judgment required to make platform and architecture decisions confidently.
• Bachelor’s degree or equivalent practical experience; an advanced degree is considered an asset but is not required.
• Experience scaling a startup or early-stage organization, including building teams, systems, and operational practices, is an asset.
• Experience working within a services or consultancy model, including SOWs, staffing, and client delivery, is an asset.
• An established professional network of engineers who could potentially contribute to a growing technical organization is an asset.
• Strong accountability, curiosity, adaptability, and comfort making important decisions with incomplete information.
• Commitment to responsible AI practices, including transparency, human oversight, privacy, and thoughtful implementation.

Benefits:

• Remote-friendly position available across Canada.
• Independent contractor arrangement for Canadian applicants.
• Preference for candidates aligned with the EST timezone.
• Periodic travel of approximately 10–20% for client work, team offsites, and industry events.
• Opportunity to lead and shape a growing technical organization, including its engineering team, delivery model, systems, and technical direction.
• Exposure to production AI systems, enterprise technology challenges, and complex client engagements.
• Inclusive, collaborative environment that values diverse perspectives and high-performing teams.