Senior Delivery Manager (AI)

Location: Remote in Canada

Salary: $170,000–$220,000 CAD

Company

Robots & Pencils is an applied AI engineering firm that designs and ships AI co-workers and enterprise digital systems, with delivery centers in Canada, the United States, Eastern Europe, and Latin America.

What you will do

• Lead end-to-end delivery of complex, multi-phase engagements across scope, budget, timeline, quality, releases, and operations transitions.
• Facilitate agile planning and execution, manage dependencies, risks, scope changes, escalations, KPIs, QA, and UAT.
• Own AI-native and agentic delivery approaches, including model risk, data readiness, evaluation strategy, definition of done, human-in-the-loop checkpoints, monitoring, and drift management.
• Set standards for AI-augmented delivery, observability, context management, latency, infrastructure, guardrails, and status visibility.
• Serve as the primary client delivery contact, communicate trade-offs and business impact to executives, and identify expansion opportunities.
• Lead distributed teams, coach delivery managers, improve delivery practices, and contribute to hiring and staffing decisions.

Requirements

• 5+ years of experience in software delivery, technical project management, or engineering leadership.
• Strong understanding of agile delivery practices such as Scrum, SAFe, or Kanban across complex, multi-team engagements.
• Experience managing distributed onshore and offshore teams and delivering complex, multi-platform digital systems.
• Strong client-facing communication and relationship-management skills.
• Experience with delivery tooling such as Jira, Confluence, GitHub, Azure DevOps, and CI/CD pipelines.
• Familiarity with cloud-native architectures and AI-enabled platforms, plus demonstrable use of AI tools such as Claude for delivery planning, reporting, and documentation.
• Experience leading at least one engagement where AI/ML or agentic capability was core to the solution, including model risk, evaluation, and client expectations.
• Experience setting standards for AI-native work and leading an agentic development or delivery process, including observability, success metrics, status visibility, infrastructure, context management, and latency trade-offs.
• Ability to identify engagement growth opportunities and bring those conversations forward with Client Partners.

Nice to have

• PMP, Scrum Master, SAFe, or equivalent certification.
• Industry depth in Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, or Manufacturing.
• Experience delivering agentic, AI co-worker, or applied-AI enterprise initiatives.
• Prior client-facing experience in engagement management, consulting, or account leadership.

Culture & Benefits

• Remote employment in Canada with distributed onshore and offshore teams.
• Teams average more than 15 years of experience and emphasize ownership, direct feedback, continuous improvement, and delivery quality.
• Benefits include paid time off, medical, dental, and vision insurance, and a 401(k) for eligible employees.
• Employment may be conditional on successful completion of a background check under local legislation.