Senior Delivery Manager (AI)

Location: Remote in Canada or the United States

Salary: $160,000–$190,000 USD annually or $170,000–$220,000 CAD annually, depending on location and qualifications.

Company

Robots & Pencils is an applied AI engineering firm that designs and ships AI co-workers integrated into enterprise operations.

What you will do

• Own end-to-end delivery of complex, multi-phase AI and digital engagements across scope, budget, timeline, quality, and production readiness.
• Facilitate sprint planning, backlog refinement, phased releases, QA, UAT, and transitions into operations and maintenance.
• Manage dependencies, risks, scope changes, escalations, delivery KPIs, and trade-offs across distributed onshore and offshore teams.
• Define and lead AI-augmented delivery processes, including observability, status visibility, evaluation metrics, human-in-the-loop checkpoints, and post-launch monitoring.
• Partner with AI product managers and engineers on model risk, data readiness, context management, latency, infrastructure, and evaluation strategy.
• Lead client communication, executive stakeholder sessions, roadmap alignment, team coaching, hiring input, and engagement expansion discussions.

Requirements

• 5+ years of experience in software delivery, technical project management, or engineering leadership.
• Strong experience with agile delivery practices across complex, multi-team engagements, including Scrum, SAFe, or Kanban.
• Experience managing distributed teams and delivering complex, multi-platform digital systems.
• Track record leading an engagement where AI/ML or agentic capability was core to the solution, including model risk, evaluation, and client expectation management.
• Experience leading an agentic development or delivery process, including observability, success metrics, status visibility, infrastructure, and context-management trade-offs.
• Strong client-facing communication skills and experience with delivery tools such as Jira, Confluence, GitHub, Azure DevOps, or CI/CD pipelines.

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.
• Previous engagement management, consulting, account leadership, or other client-facing experience.

Culture & Benefits

• Remote work available in Canada or the United States.
• Paid time off and medical, dental, and vision insurance for eligible employees.
• 401(k) benefits for eligible employees.
• Work with experienced teams averaging more than 15 years of experience.
• Culture centered on ownership, direct feedback, continuous improvement, and high-quality delivery.

Hiring process

• Employment may be conditional on a background check in accordance with local legislation.
• Executive interviews are part of the firm's hiring process for engineers, designers, and other engagement roles.