Delivery Manager

Robots and Pencils

$120K — $150K *
US-AnywhereRemote in Canada
Education, Government & Non-Profit
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 10+ years in software development or technical delivery
  • Track record of successfully delivering complex projects in agile frameworks
  • Experience working with engineering teams on AI systems
  • Proficient with tools like Jira, Confluence, Microsoft Office, Google Workspace, and Lucid
  • Ability to utilize delivery metrics and performance data for strategic optimization
  • Strong interpersonal skills for managing executive-level relationships
  • Relevant certifications like PMP or Scrum Master are preferred
  • Familiarity with AI tools, particularly Claude, for operational efficiency
  • Experience in higher education environments or complex documentation engagements is a plus

Responsibilities

  • Lead and maintain focus and accountability within the AI delivery pod
  • Own the delivery operating model, ensuring effective sprint cadence and communication
  • Identify and manage dependencies and risks proactively
  • Collaborate with both the Robots & Pencils team and client teams to maintain momentum
  • Surface potential blockers early to mitigate issues before they escalate
  • Drive high-quality delivery against priorities on a weekly basis
  • Foster strong client relationships at the operational level during project execution

Benefits

  • High-visibility and fast-paced work environment
  • Opportunity to shape AI practices at a major online university
  • Engagement with an ambitious client committed to AI transformation
  • Development of a reference model for scaling AI across an institution
  • Collaboration with a cross-functional, high-performing team
Full Job Description
Robots & Pencils has been engaged by a major online university to stand up an integrated AI Pod - an embedded, cross-functional delivery team building and deploying AI-enabled systems across institutional workflows. This is a high-visibility, high-velocity engagement with a client that is serious about AI transformation and committed to moving fast.

The pod operates as both a delivery unit and a reference model. The practices, sprint rhythms, and operating patterns established here become the blueprint the university replicates as it scales AI across the institution.

We are looking for an experienced Delivery Lead to keep the pod focused, moving, and accountable. This person owns the delivery operating model - sprint cadence, dependency management, risk identification, and stakeholder communication. You will work across both the R&P team and client-side counterparts, maintaining momentum through ambiguity, surfacing blockers before they become problems, and ensuring the pod delivers against priorities week over week.

The right person for this role is not a project manager who tracks status. They are a delivery operator who understands AI product development, knows how to run a high-performing pod, and can hold a team accountable while maintaining strong client relationships at the operational level.

This is not a coordination role. It is an execution and accountability role in a fast-moving, high-stakes client engagement.

Required Skills & Experience
  • 10+ years in software development or technical delivery
  • Proven success delivering complex projects in agile environments, meeting demanding timelines and quality expectations
  • Comfort working alongside engineering teams building agentic systems
  • Strong familiarity with tools such as: Jira/Confluence/Microsoft Office/Google/Lucid
  • Ability to leverage delivery metrics and performance data to inform strategies and optimize outcomes
  • Exceptional interpersonal and stakeholder management skills; confident managing executive-level relationships and escalations
  • PMP, Scrum Master, or other relevant technical/project management certifications are highly desirable
  • In-depth knowledge of AI tools such as Claude and use in day-to-day work for increased efficiency
  • Experience working with education or higher education environments, or leading complex discovery and operational documentation engagements, is a strong plus


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