Senior Delivery Manager (AI)

TL;DR

Senior Delivery Manager (AI): Managing the end-to-end execution of complex AI engineering engagements for enterprise clients with an accent on distributed team leadership and regulatory compliance. Focus on deploying production-ready AI systems, coordinating multi-platform architectures, and driving business impact for healthcare and financial services stakeholders.

Location: Cleveland, OH (Remote Friendly)

Company

Applied AI engineering firm specializing in building AI co-workers and business architecture for enterprise operations across various industries.

What you will do

• Lead end-to-end delivery of multi-phase AI engagements, ensuring alignment on scope, budget, timeline, and quality.
• Facilitate agile ceremonies, including sprint planning and backlog refinement across one or more cross-functional teams.
• Manage phased releases, production readiness, and transitions into operations and maintenance models.
• Coordinate split architectures (e.g., AWS application layer and Azure data layer), managing API contracts and event-schema alignment.
• Serve as the primary delivery contact for clients, translating technical progress into business ROI and identifying expansion opportunities.
• Lead and coach distributed onshore and offshore teams while contributing to firm-wide delivery practices and frameworks.

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).
• Strong understanding of agile delivery practices (Scrum, SAFe, Kanban) and delivery tooling (Jira, Confluence, GitHub, Azure DevOps).
• Ability to communicate progress and trade-offs clearly to executive and non-technical stakeholders.
• Familiarity with cloud-native architectures, AI platforms, and EHR/health-data integration concepts (Epic, HL7v2/FHIR).
• Demonstrable usage of AI tools (e.g., Claude) to enhance delivery planning, reporting, and documentation.

Nice to have

• Deep understanding of the healthcare industry, particularly clinical/virtual care delivery and EHR workflows.
• Experience delivering agentic, AI co-worker, or applied-AI initiatives in an enterprise setting.
• Prior career experience in client-facing roles such as engagement management or strategic consulting.

Culture & Benefits

• Work within a high-seniority environment where teams average 15+ years of experience.
• Culture of ownership, direct honest feedback, and an obsession with technical craft.
• Fast-paced environment focused on shipping exceptional, production-ready work.
• Emphasis on continuous learning to keep pace with the rapidly evolving AI landscape.
• Collaborative environment that values resourcefulness and calmness under pressure.