Senior AI Transformation Program Manager (Remote)

Robots and Pencils; Canada; Remote; CAD 203,000 - 238,000; Full time

Benefits offered by this job

Paid time off

Medical insurance

Dental insurance

Vision insurance

401(k)

Job summary

Robots & Pencils is seeking a Technical Program Manager to oversee large, multi-workstream AI and cloud transformation programs. You will translate client business goals into technical plans, coordinate architecture discussions, and drive successful launches across distributed teams.

You will facilitate collaboration between business and engineering leads, define governance, align priorities, and ensure delivery remains on schedule and within budget, while delivering measurable business value.

Qualifications

• 5+ years of experience leading multiple Agile teams concurrently or at scale.
• 5+ years of experience delivering enterprise IT engagements.
• Proven track record leading large-scale AI, digital, or cloud transformation programs.
• Experience with delivery tooling: Jira, Confluence, GitHub, Azure DevOps, CI/CD pipelines.
• Ability to distill customer needs into technical requirements and map to business outcomes.
• Daily use of AI tools to enhance planning, reporting, and documentation.

Responsibilities

• Own end-to-end delivery of large-scale AI, digital, and cloud programs from strategy to value realization.
• Break complex programs into manageable workstreams with clear ownership and sequencing.
• Drive program schedules across multiple Agile teams with aligned plans.
• Define KPIs and governance; report program health to guide decisions.
• Bridge business requirements and technical solutions to deliver outcomes.
• Lead stakeholder alignment with client executives and partner teams.

Skills

Agile leadership

Stakeholder management

Program strategy

Technical/architecture understanding

Tools

Jira

Confluence

GitHub

Azure DevOps

CI/CD pipelines

Job description

Robots & Pencils is seeking a Technical Program Manager to oversee large, multi-workstream AI and cloud transformation programs. You will translate client business goals into technical plans, coordinate architecture discussions, and drive successful launches across distributed teams.

You will facilitate collaboration between business and engineering leads, define governance, align priorities, and ensure delivery remains on schedule and within budget, while delivering measurable business value.