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. 

Position Overview  

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. 

Why This Role Matters  

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. 

What You’ll Do  

Craft & Delivery  

• 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 

Collaboration & Communication  

• 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 

Leadership & Influence  

• 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 

• Contribute to improving delivery practices, tools, and frameworks across engagements  

• Assess team strengths and gaps on your engagements, and partner with Client Partners to flag staffing needs and high-potential talent for the firm 

• Conduct executive interviews for engineers, designers, and other roles joining your engagements, and serve as an essential voice in go/no-go hiring decisions across the firm 

What You’ll Bring  

• 5+ years of experience in software delivery, technical project management, or engineering leadership  

• Experience delivering in HIPAA-regulated or other compliance-heavy environments (healthcare, financial services, government) - this role involves PHI, a Business Associate Agreement, and HIPAA-eligible infrastructure. 

• Strong understanding of agile delivery practices across complex, multi-team engagements (e.g., Scrum, SAFe, Kanban)  

• Experience managing distributed teams across onshore and offshore locations  

• Comfort working with clinical stakeholders and executives who are not primarily technical. 

• Proven ability to deliver complex, multi-platform digital systems in agile environments  

• Strong client-facing communication and relationship management skills  

• Experience with delivery tooling (e.g., Jira, Confluence, GitHub, Azure DevOps, CI/CD pipelines)  

• Familiarity with cloud-native architectures and AI-enabled platforms  

• Familiarity with EHR/health-data integration concepts (e.g., Epic, HL7v2/FHIR) sufficient to coordinate with a client-owned data layer  

• Demonstrable usage of AI tools to enhance delivery planning, reporting, and documentation (e.g., Claude)  

• PMP, Scrum Master, SAFe, or equivalent certification preferred  

• Instinct for spotting where an engagement can grow, and the credibility with clients to bring those conversations forward with Client Partners 

Helpful Extras and Unique Skills  

• Deep understanding of the healthcare industry, ideally clinical/virtual care delivery (virtual nursing, hospital operations, EHR workflows) 

• Experience delivering agentic, AI co-worker, or applied-AI initiatives in enterprise 

• Prior career experience in client-facing roles (engagement management, consulting, account leadership) that informs growth conversations 

You’ll Do Well Here if You Are  

• A doer.  You see something broken and fix it. You'd rather move on clarity than wait for certainty. 

• A fast learner who knows you don't know everything.  The AI landscape changes weekly. You're senior enough to know better and curious enough to keep learning anyway. 

• Direct in a way that makes the work better.  You give honest feedback. You'd rather have the hard conversation than blow smoke. 

• Obsessed with craft.  You know genius is in the details. You ship exceptional, not perfect, and you don't put your name on work you wouldn't stand behind. 

• Built for ownership.  You honor commitments, admit mistakes fast, and back your teammates when a decision costs something. No handoffs, no finger-pointing. 

• All in.  You treat clients' businesses like your own. You take the work seriously without taking yourself seriously. 

• Resourceful when the budget, timeline, or team is tight.  Constraints don't slow you down. They sharpen you. 

• Calm when it gets hot.  When scope, timeline, and stakeholders pull in three directions, you slow the room down enough to make the right call. You’d rather raise the hard trade-off in week two than absorb it in week eight. 

• Glad to be in the room with people who care as much as you do.  Our teams average fifteen-plus years of experience. We hire people who push each other to do better work.