Technical Program Manager

Robots & Pencils

. Own end-to-end delivery of large-scale ($10M+) AI, digital, and cloud transformation programs from strategy and roadmap through launch and realized business value .

Posted 11/4/2026full-timeRemote • Canada, United StatesMid-LevelSenior💰 CA$191,226 - CA$238,426 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading large-scale AI, digital, and cloud transformation programs, with a strong focus on Agile methodologies, technical architecture, and program governance. Capable of bridging business and technical requirements while driving successful outcomes through effective communication and stakeholder management.

Highest-signal resume keywords

AI Transformation Program LeadershipAgile Team ManagementCloud Adoption Framework ApplicationTechnical Architecture ExpertiseAI Tools Utilization

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Applicant Tracking System Keywords

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Hard Skills

AI Development Life CycleProgram-Level KPIs DefinitionCloud-Native DesignFrontend TechnologiesBack-End TechnologiesTechnical Requirements SpecificationModel Risk ManagementEvaluation StrategyHuman-in-the-Loop CheckpointsPost-Launch Monitoring

Soft Skills

Stakeholder CommunicationAmbiguity ManagementMentoringClient PartnershipEscalation Management

Tools & Technologies

JiraConfluenceGitHubAzure DevOpsCI/CD PipelinesClaude

Industry Keywords

Digital TransformationCloud TransformationAI/ML SolutionsWell-Architected FrameworkEnterprise-Level IT Engagements

Tech Stack

Tools & technologies

AzureCloud

About the role

Key responsibilities & impact

Own end-to-end delivery of large-scale ($10M+) AI, digital, and cloud transformation programs from strategy and roadmap through launch and realized business value
Break complex programs into manageable workstreams with clear ownership, sequencing, and dependencies
Drive schedules across multiple concurrent Agile teams and maintain an integrated plan
Define program-level KPIs and governance and report program health across scope, timeline, budget, and quality
Bridge business requirements and technical solutions and help drive technical direction
Facilitate engineering and architecture discussions and decompose technical problems into deliverable solutions
Contribute to technical documentation and define documentation standards
Own the AI Development Life Cycle at the program level
Define standards for AI-driven features, including evaluation thresholds, human-in-the-loop checkpoints, and post-launch monitoring
Partner with AI engineering leads on model risk, data readiness, evaluation strategy, and observability
Define success metrics for AI-augmented delivery and drive status visibility across AI pipelines
Evaluate when an agentic approach is inappropriate based on context management, latency, infrastructure, and cost
Use AI tools such as Claude for planning, specifications, reporting, and stakeholder communication
Serve as senior program partner to client executives and manage escalations and trade-off decisions
Communicate schedules, progress, and business impact to stakeholders and senior leaders
Partner with Client Partners on follow-on work and expansion opportunities
Lead and mentor Senior Delivery Managers and Delivery Managers
Shape the company’s delivery practice, tools, and frameworks
Assess staffing and capability gaps and partner on staffing needs and talent
Conduct executive interviews and contribute to go/no-go hiring decisions

Requirements

What you’ll need

5+ years of experience leading multiple Agile teams concurrently or at scale
5+ years of experience leading and delivering enterprise-level IT engagements
Proven track record leading large-scale ($10M+) AI, digital, or cloud transformation programs from strategy through to realized business value
Practical application of Well-Architected and Cloud Adoption Framework frameworks
Strong technical foundation in architecture, frontend and back-end technologies, cloud-native design, technical requirements, and functional specifications
Experience leading programs where AI/ML or agentic capability was core to the solution, including model risk, evaluation, client expectations, human-in-the-loop checkpoints, and monitoring
Demonstrable daily use of AI tools such as Claude
Experience with Jira, Confluence, GitHub, Azure DevOps, and CI/CD pipelines
Comfort operating in ambiguity and bringing growth conversations forward with Client Partners
Background check may be required as a condition of employment

Benefits

Comp & perks

Paid time off
Medical insurance
Dental insurance
Vision insurance
401(k)