Senior Delivery Manager (AI)

Location: Canada — Remote

Salary: CAD 170,000–220,000 annually

Company

Robots & Pencils is an applied AI engineering firm building and shipping AI co-workers and enterprise solutions, 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, and delivery commitments.
• Facilitate sprint planning, backlog refinement, phased releases, production readiness, QA, UAT, and transitions into operations and maintenance.
• Manage dependencies, risks, scope changes, escalations, delivery KPIs, and trade-offs across distributed cross-functional teams.
• Own AI-native and agentic delivery approaches, including AIDLC adoption, evaluation, observability, context management, latency, infrastructure, guardrails, and post-launch monitoring.
• Serve as the primary client delivery contact, communicate progress and business impact to executive stakeholders, and identify expansion opportunities.
• Lead and mentor delivery managers, improve delivery practices, assess staffing needs, and participate in executive hiring decisions.

Requirements

• 5+ years of experience in software delivery, technical project management, or engineering leadership.
• Strong understanding of agile delivery practices across complex, multi-team engagements, including Scrum, SAFe, or Kanban.
• Experience managing distributed onshore and offshore teams and delivering complex, multi-platform digital systems in agile environments.
• 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.
• Track record leading at least one engagement where AI/ML or agentic capability was core to the solution, including model risk, evaluation, and client expectations.
• Ability to set standards for AI-native work, including evaluation criteria, human-in-the-loop checkpoints, monitoring, observability, success metrics, status visibility, infrastructure, context management, and latency trade-offs.
• Experience leading a team through an agentic development or delivery process, not only using AI tools personally.

Nice to have

• PMP, Scrum Master, SAFe, or equivalent certification.
• Experience in Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, or Manufacturing.
• Experience delivering agentic, AI co-worker, or applied-AI initiatives in enterprise environments.
• Prior client-facing experience in engagement management, consulting, or account leadership.
• Experience identifying engagement growth opportunities and shaping follow-on work with Client Partners.

Culture & Benefits

• Remote work from Canada with distributed onshore and offshore teams.
• Culture emphasizes ownership, direct feedback, continuous improvement, craftsmanship, resourcefulness, and calm decision-making under pressure.
• Teams average 15+ years of experience and work with senior engineering, UX, AI product, and delivery professionals.
• Comprehensive benefits include paid time off, medical, dental, and vision insurance, and 401(k) for eligible employees.
• Employment may be conditional on a background check in accordance with local legislation.