Senior Delivery Manager (AI)

Location: Canada, remote-friendly

Salary: CAD 160,000–200,000 per year

Company

Robots & Pencils is an applied AI engineering firm that designs and ships AI co-workers for enterprise operations, combining AWS, UX, and senior engineering expertise.

What you will do

• Lead end-to-end delivery of complex, multi-phase engagements across scope, budget, timeline, quality, and production readiness.
• Facilitate agile planning, backlog refinement, phased releases, QA, UAT, and transitions into operations and maintenance.
• Manage dependencies, risks, scope changes, escalations, delivery KPIs, and status visibility across AI-driven pipelines.
• Define and implement AI-augmented delivery practices, including evaluation standards, human-in-the-loop checkpoints, monitoring, observability, and success metrics.
• Partner with AI product managers and engineers on model risk, data readiness, infrastructure, context management, latency, and agentic delivery trade-offs.
• Serve as the primary client delivery contact, lead executive communication, identify expansion opportunities, and coach delivery managers across distributed teams.

Requirements

• 5+ years of experience in software delivery, technical project management, or engineering leadership.
• Strong experience with agile delivery across complex, multi-team engagements and distributed onshore/offshore teams.
• Proven ability to deliver complex, multi-platform digital systems and manage client relationships.
• Experience with delivery tools such as Jira, Confluence, GitHub, Azure DevOps, and CI/CD pipelines, plus familiarity with cloud-native architectures and AI-enabled platforms.
• Track record leading AI/ML or agentic engagements, including model risk, evaluation, client expectations, observability, success metrics, and status visibility.
• Ability to define AI-native delivery standards and coach other delivery managers on evaluation, monitoring, infrastructure, context management, and latency trade-offs.

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 enterprise initiatives.
• Client-facing experience in engagement management, consulting, or account leadership.

Culture & Benefits

• Work with senior teams averaging more than 15 years of experience.
• Culture centered on ownership, direct feedback, continuous improvement, and high-quality delivery.
• Paid time off and medical, dental, and vision insurance.
• 401(k) benefits for eligible employees.

Hiring process

• Employment may be conditional on successfully completing a background check in accordance with local legislation.