Technical Program Manager

This position is listed on behalf of a partner company, which manages all applications and next steps. Our partner is looking for a Technical Program Manager based in Canada.

This is a senior leadership opportunity to drive complex, large-scale enterprise technology transformations within a fast-growing applied AI and engineering environment. As a Technical Program Manager, you will oversee the full lifecycle of major AI, cloud, and digital transformation programs, translating business objectives into actionable technical strategies and measurable outcomes. You will coordinate multiple Agile teams, align engineering and business stakeholders, and ensure successful delivery across complex, multi-workstream initiatives. Working closely with client executives and technical leaders, you will influence architectural decisions, manage risks, and navigate competing priorities while maintaining delivery quality and momentum. You will also play a central role in integrating AI-driven solutions into enterprise operations, establishing standards for responsible development, evaluation, and deployment. This position offers significant ownership, strategic influence, and the opportunity to shape innovative delivery practices alongside highly experienced, distributed engineering teams.

Accountabilities:

• Lead the end-to-end delivery of large-scale enterprise AI, digital, and cloud transformation programs, including engagements valued at $10 million or more, from initial strategy and roadmap development through implementation, launch, and measurable business outcomes.
• Break down complex programs into manageable workstreams, establishing clear responsibilities, delivery milestones, sequencing, dependencies, and accountability across teams.
• Coordinate multiple concurrent Agile teams, including engineering, product management, Scrum Masters, and delivery leaders, ensuring alignment around an integrated program plan.
• Establish program-level governance frameworks, performance indicators, and reporting processes to monitor scope, timelines, budgets, quality, risks, and overall delivery health.
• Translate business objectives and customer requirements into technical specifications, functional requirements, and actionable engineering priorities, ensuring every technical decision supports a defined business outcome.
• Facilitate architecture and engineering discussions, collaborating with technical leads to guide solution design and maintain a strong understanding of frontend, backend, and cloud-native technologies.
• Break down complex technical challenges into practical solutions and deliverable initiatives, helping teams make informed decisions and maintain implementation momentum.
• Own the AI Development Life Cycle (AIDLC) at the program level, establishing consistent delivery standards and ensuring Senior Delivery Managers apply these practices across individual workstreams.
• Define program-wide quality standards for AI-driven and probabilistic features, including evaluation thresholds, human-in-the-loop validation checkpoints, post-launch monitoring, and performance expectations.
• Partner with AI engineering leaders to assess model risks, data readiness, evaluation strategies, and observability requirements, translating technical uncertainties into actionable plans and risk management frameworks.
• Establish success metrics for AI-augmented delivery, measuring quality, development velocity, rework, review requirements, and overall operational effectiveness.
• Evaluate when agentic AI approaches are appropriate for client needs, considering technical feasibility, context management, latency, infrastructure requirements, and cost implications.
• Integrate AI tools into everyday program management activities, including planning, specifications, reporting, documentation, and stakeholder communication, while encouraging adoption across delivery teams.
• Act as a senior strategic partner to client executives, building trusted relationships through transparent communication, consistent delivery, and a clear understanding of business priorities.
• Anticipate delivery bottlenecks, manage escalations, resolve stakeholder misalignment, and facilitate decisions when business objectives, technical constraints, timelines, and resources compete.
• Communicate program progress, delivery schedules, risks, and business impact to senior stakeholders, ensuring visibility into both execution and realized value.
• Collaborate with Client Partners to identify follow-on projects, expansion opportunities, and additional ways to deliver value to existing clients.
• Mentor and support Senior Delivery Managers and Delivery Managers through actionable feedback, coaching, and opportunities for professional development.
• Contribute to the evolution of delivery methodologies, internal frameworks, tools, and operational practices beyond individual client engagements.
• Evaluate staffing requirements, identify capability gaps, support resource planning, and collaborate with leadership on talent development and recruitment decisions.
• Participate in executive-level interviews and contribute to hiring recommendations and strategic talent decisions.

Requirements:

• At least 5 years of experience leading multiple Agile teams concurrently or at scale, including collaboration with Scrum Masters, Product Owners, engineering teams, and product stakeholders.
• At least 5 years of experience managing and delivering enterprise-level IT engagements, ideally within consulting, technology services, or digital transformation environments.
• Proven track record of leading large-scale AI, digital, or cloud transformation programs valued at $10 million or more, from strategic planning through implementation and measurable business results.
• Strong understanding of program management methodologies, Agile delivery practices, and enterprise governance, with the ability to manage complex dependencies, budgets, timelines, and competing priorities.
• Practical experience applying cloud architecture frameworks and methodologies, such as AWS Well-Architected Framework and Cloud Adoption Framework, to support technical decision-making and solution governance.
• Strong technical foundation, with the ability to engage credibly in architecture discussions, understand frontend and backend technologies, evaluate cloud-native solutions, and translate complex technical challenges into executable plans.
• Demonstrated ability to convert customer business needs into clear technical requirements, functional specifications, and measurable delivery objectives.
• Experience managing enterprise programs where AI, machine learning, or agentic capabilities were central to the solution, including exposure to model risk management, evaluation strategies, and client expectations.
• Ability to establish program-wide AI quality standards, including evaluation criteria, human oversight mechanisms, monitoring practices, and responsible implementation processes.
• Demonstrable daily use of AI tools, such as Claude or equivalent solutions, to improve planning, documentation, specifications, reporting, and communication.
• Familiarity with engineering and program delivery tools, including Jira, Confluence, GitHub, Azure DevOps, and CI/CD pipelines.
• Excellent stakeholder management and executive communication skills, with the confidence to lead discussions, facilitate difficult decisions, and manage client relationships at senior levels.
• Strong leadership and mentoring capabilities, with experience guiding delivery professionals, developing teams, and promoting accountability and continuous improvement.
• Comfortable working in ambiguous, fast-paced environments where priorities evolve and decisions must often be made with incomplete information.
• Commercial awareness and the ability to identify opportunities for additional client engagement and business growth in collaboration with Client Partners.
• A proactive, resourceful, and ownership-driven mindset, combined with strong judgment, adaptability, attention to detail, and the ability to remain composed under pressure.

Nice-to-have qualifications:

• Industry experience in one or more of the following sectors: Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, or Manufacturing.
• Experience delivering enterprise AI initiatives, agentic AI solutions, AI co-workers, or applied AI transformation programs.
• Extensive knowledge of AWS services, cloud architectures, and best practices, with the ability to guide technical strategy and architectural decisions.
• Previous ownership of complex, multi-workstream agentic AI transformation programs from initial planning through production deployment.
• Previous experience in client-facing consulting, engagement management, account leadership, or strategic client relationship management.
• Experience influencing organizational delivery practices and implementing scalable frameworks across distributed engineering teams.

Benefits:

• Competitive compensation: Annual salary range of CA$202,589 to CA$238,426 for the Canadian market, depending on qualifications, experience, skills, seniority, and geographic location.
• Comprehensive healthcare coverage: Medical, dental, and vision insurance for eligible employees.
• Retirement benefits: Access to a 401(k) retirement savings plan for eligible employees.
• Paid time off: Paid leave to support work-life balance and personal well-being.
• Remote flexibility: Fully remote working arrangement, with the opportunity to work from Canada or the United States.
• International collaboration: Work alongside highly experienced, distributed engineering and delivery teams across multiple regions.
• Professional development: Opportunities to expand expertise in enterprise AI, cloud transformation, and emerging technologies.
• Leadership opportunities: Significant ownership and influence over major enterprise programs, delivery frameworks, and organizational practices.
• Innovative environment: Opportunity to work on advanced AI solutions, including agentic AI and AI-powered enterprise applications.
• Experienced colleagues: Collaborate with multidisciplinary professionals whose teams average more than 15 years of industry experience.

How Jobgether works:

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

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