Senior Delivery Manager

Robots and Pencils•Cleveland, OH

About The Position

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.

Requirements

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

Nice To Haves

PMP, Scrum Master, SAFe, or equivalent certification preferred
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

Responsibilities

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
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