Senior Delivery Manager

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 fast, sweat the details, and build things that actually ship.

As a Senior Delivery Manager, you are the senior delivery authority on a cross-functional engagement: owning execution from kickoff through release, leading distributed onshore-and-offshore teams, and serving as the primary delivery partner to the client. You bring the judgment to navigate ambiguity, the discipline to keep complex programs on track, and the instinct to make every engagement a foundation for the next one.

Senior Delivery Managers are where Robots and Pencils’ promise of “production-ready AI in 30 to 45 days” actually has to hold. On the engagements you run, you set the pace of delivery, the discipline behind it, and the trust that decides whether the client comes back for more. The work moves only as fast as someone is willing to own the plan, surface trade-offs early, and keep distributed teams pulling in the same direction.

• Lead end-to-end delivery of complex, multi-phase engagements, ensuring alignment across scope, budget, timeline, and quality to meet delivery commitments and achieve successful outcomes

• Facilitate sprint planning, backlog refinement, and delivery execution across one or more cross-functional teams

• Facilitate milestone-sprint demos and client sign-off against defined acceptance criteria (e.g., clinical UAT), managing a deemed-acceptance review cadence

• Manage phased releases, production readiness, and transitions into operations and maintenance models

• Coordinate delivery across a split architecture owned by two parties (e.g., Provider-owned AWS application layer / Client-owned Azure data layer), including API contract and event-schema alignment

• Identify and proactively manage dependencies, risks, scope changes, and escalations before they become blockers

• Define, track, and report delivery KPIs, using data to guide decisions, manage delivery health, and inform tradeoffs across scope, timeline, and budget

• Support QA and UAT efforts, ensuring quality is validated and outcomes meet agreed acceptance criteria

• Bring an AI-forward mindset to your daily work, using tools like Claude to enhance delivery planning, reporting, and stakeholder communications

• Serve as the primary delivery contact for clients, building trusted relationships through transparency, consistency, and clear communication while identifying opportunities to expand value within the engagement

• Lead stakeholder working sessions, roadmap alignment discussions, and delivery forums with confidence

• Communicate progress, risks, and tradeoffs clearly to executive and non-technical audiences

• Partner with Client Partners to spot expansion opportunities inside the engagement (scope, follow-on work, new use cases) and help shape the case for what’s next

• Translate delivery progress into business impact for client stakeholders (ROI, milestones, decisions) so executives see ongoing value, not just status

• Lead distributed delivery teams across onshore and offshore locations, fostering accountability, collaboration, and delivery excellence

• Coach junior delivery managers with concrete feedback and stretch opportunities, contributing to their development plans

• Foster a culture of transparency, continuous improvement, and high performance across the engagement

• Con…