Technical Program Manager (AI)

Location: US Remote is listed; the role requires 3 days per week on-site in New York City or Mountain View, California, with approximately 20% client travel.

Salary: $180,000–$215,000 USD per year. Benefits include paid time off, medical, dental and vision insurance, and 401(k) for eligible employees.

Company

Robots & Pencils is an applied AI engineering firm that designs and delivers AI co-workers, cloud solutions, and enterprise technology transformations for clients across multiple industries.

What you will do

• Own end-to-end delivery of large-scale, $10M+ AI, digital, and cloud transformation programs from strategy and roadmap through launch and realized business value.
• Structure complex programs into workstreams, define ownership and dependencies, and coordinate schedules across concurrent Agile teams.
• Translate business goals into technical requirements, facilitate architecture and engineering discussions, and guide technical direction across frontend, backend, and cloud-native solutions.
• Own the program-level AI Development Life Cycle, including evaluation thresholds, human-in-the-loop checkpoints, monitoring, model risk, data readiness, and observability.
• Manage executive and client stakeholder alignment, escalations, trade-offs, program governance, KPIs, and reporting on scope, timeline, budget, quality, and business impact.
• Lead and mentor Delivery Managers and Senior Delivery Managers, shape delivery practices, assess staffing needs, and participate in executive interviews and go/no-go hiring decisions.

Requirements

• 5+ years of experience leading multiple Agile teams, including Scrum Masters and Product Owners, concurrently or at scale.
• 5+ years of experience leading and delivering enterprise-level IT engagements.
• Proven experience leading large-scale, $10M+ AI, digital, or cloud transformation programs from strategy through realized business value.
• Practical application of Well-Architected and Cloud Adoption Framework principles for program decisions and solution governance.
• Strong technical foundation covering architecture, frontend and backend technologies, cloud-native design, technical requirements, functional specifications, and decomposition of complex technical problems.
• Experience leading programs where AI/ML or agentic capability was core to the solution, including model risk, evaluation, client expectations, human-in-the-loop checkpoints, and monitoring.
• Demonstrable daily use of AI tools such as Claude for planning, specifications, reporting, and documentation.
• Experience with delivery and engineering tools including Jira, Confluence, GitHub, Azure DevOps, and CI/CD pipelines.
• Comfort operating in ambiguity and credibility with clients to bring growth conversations forward with Client Partners.

Nice to have

• Industry depth in Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, or Manufacturing.
• Experience delivering agentic, AI co-worker, or applied-AI initiatives in enterprise environments.
• Comprehensive knowledge of AWS services, architectures, and best practices.
• End-to-end ownership of complex, multi-workstream agentic AI transformation programs.
• Prior client-facing experience in engagement management, consulting, or account leadership.

Culture & Benefits

• Work in an innovative, fast-moving environment where ambiguity and conflicting priorities are common.
• Teams are designed to be senior and average more than 15 years of experience.
• Culture emphasizes ownership, direct feedback, continuous learning, craftsmanship, and practical problem-solving.
• Paid time off, medical, dental and vision insurance, and 401(k) are available to eligible employees.
• Background checks may be required as a condition of employment in accordance with local legislation.