Location: Remote in US or Canada | Travel: RegularCompany Overview Robots & Pencils is an applied AI engineering firm building the next frontier of business architecture. We design and ship AI co-workers that integrate into enterprise operations and deliver measurable results for our clients. We're all in on AWS, combining deep UX capability with senior engineering talent to get AI into production fast and keep it there.We’ve earned the trust of leaders across Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, and Manufacturing and more, and earned a reputation as the nimble alternative to traditional global systems integrators. Founded in 2009, with delivery centers in Canada, the United States, Eastern Europe, and Latin America, we are smaller, faster, and more senior by design. Our teams average 15+ years of experience. We move rapid, sweat the details, and build things that actually ship.Position Overview As a Delivery Manager, you own delivery on a cross-functional project: leading the team from kickoff through release, coordinating onshore and offshore contributors, and serving as a key delivery partner to the client. You bring the discipline to keep work on track, the judgment to navigate everyday trade-offs, and the ownership to make sure the project lands.Why This Role Matters Delivery Managers are where Robots and Pencils’ promise of “production-ready AI in 30 to 45 days” turns into actual project plans, sprint cadences, and shipped work. On the projects you run, you set the pace of delivery, the discipline behind it, and the trust that builds when the team consistently ships on time. The work moves only as fast as someone is willing to own the plan, surface trade-offs early,



and keep the team pulling in the same direction.What You’ll Do Craft & Delivery Lead end-to-end delivery of cross-functional projects, ensuring alignment across scope, budget, timeline, and quality to meet delivery commitments and achieve successful outcomesFacilitate sprint planning, backlog refinement, and delivery execution across one or more cross-functional teamsManage releases, production readiness, and transitions into operations and maintenance modelsIdentify and proactively manage dependencies, risks, scope changes, and escalations before they become blockersDefine, track, and report delivery KPIs, using data to guide decisions, manage delivery health, and inform tradeoffs across scope, timeline, and budgetSupport QA and UAT efforts, ensuring quality is validated and outcomes meet agreed acceptance criteriaBring an AI-forward mindset to your daily work, using tools like Claude to enhance delivery planning, reporting, and stakeholder communicationsServe as the primary delivery contact for clients, building trusted relationships through transparency, consistency, and clear communicationLead stakeholder working sessions and delivery forums with confidenceCommunicate progress, risks,



and tradeoffs clearly to executive and non-technical audiencesSupport Senior Delivery Managers and Client Partners in identifying opportunities to expand value within the engagementLeadership & Influence Lead delivery teams across onshore and offshore locations, fostering accountability, collaboration, and delivery excellenceMentor delivery coordinators and team members on your project, sharing knowledge and supporting their growthFoster a culture of transparency, continuous improvement, and high performance across the engagementContribute to improving delivery practices, tools, and frameworks across engagementsParticipate in interviews for project team members and contribute input to hiring decisionsWhat You’ll Bring 3+ years of experience in software delivery, technical project management, or engineering leadershipStrong understanding of agile delivery practices (e.G., Scrum, Kanban)Experience managing distributed teams across onshore and offshore locationsAbility to deliver multi-platform digital systems in agile environmentsStrong client-facing communication and relationship management skillsExperience with delivery tooling (e.G., Jira, Confluence, Git Hub, Azure Dev Ops, CI/CD pipelines)Familiarity with cloud-native architectures and AI-enabled platformsDemonstrable usage of AI tools to enhance delivery planning, reporting, and documentation (e.G., Claude)Scrum Master or equivalent certification preferredExperience in regulated environments (e.G., utilities, government, finance) is a plusHelpful Extras and Unique Skills Vertical depth in one or more of Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, or ManufacturingExperience delivering agentic, AI co-worker, or applied-AI initiatives in enterprisePrior career experience in client-facing roles (engagement management, consulting,

📌 Delivery Manager (Toronto)
🏢 Robots and Pencils
📍 Toronto