Technical Program Manager

Robots and Pencils•New York City, NY

11d•$180,000 - $215,000•Hybrid

About The Position

Robots & Pencils is an applied AI engineering firm that designs and delivers AI co-workers for enterprise operations. The Technical Program Manager owns the full arc of large, multi-workstream programs, translating client business goals into technical plans and guiding delivery through launch and realized business value. The role bridges business and engineering, facilitating architecture and engineering discussions, shaping technical direction with engineering leads, and aligning distributed teams around shared outcomes. The role leads enterprise AI, digital, and cloud transformation programs, including engagements valued at $10M or more. It establishes integrated plans, governance, KPIs, and delivery standards; guides technical and AI-related decisions; manages risks and trade-offs; and serves as a senior partner to client executives. The Technical Program Manager also mentors delivery managers, contributes to the firm's delivery practice, and partners with Client Partners on staffing and follow-on opportunities. The position is on-site three days per week in New York City or Mountain View, California, and requires approximately 20% client travel. The stated salary range is $180,000–$215,000 USD. Eligible employees receive paid time off, medical, dental, and vision insurance, and a 401(k).

Requirements

At least 5 years of experience leading multiple Agile teams concurrently or at scale, including Scrum Masters and Product Owners.
At least 5 years of experience leading and delivering enterprise-level IT engagements.
A proven track record leading large-scale ($10M+) AI, digital, or cloud transformation programs from strategy through realized business value.
Practical application of frameworks such as Well-Architected and Cloud Adoption Framework to inform program decisions and solution governance.
Strong technical foundation and ability to engage credibly on architecture, frontend and back-end technologies, and cloud-native design.
Ability to decompose complex technical problems into deliverable solutions, translate customer needs into technical requirements and functional specifications, and map them to business outcomes.
Experience leading programs where AI/ML or agentic capability was core to the solution, including managing model risk, evaluation, and client expectations.
Ability to set program-wide standards for AI evaluation, human-in-the-loop checkpoints, and monitoring.
Demonstrable daily use of AI tools such as Claude to improve planning, specifications, reporting, and documentation.
Experience with delivery and engineering tools such as Jira, Confluence, GitHub, Azure DevOps, and CI/CD pipelines.
Comfort operating amid ambiguity and credibility with clients to bring growth conversations forward with Client Partners.

Nice To Haves

Vertical depth in one or more of Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, or Manufacturing.
Experience delivering agentic, AI co-worker, or applied-AI initiatives in an enterprise setting.
Comprehensive knowledge of AWS services, architectures, and best practices, applied to technical decisions and strategic planning.
Ownership of end-to-end delivery for complex, multi-workstream agentic AI transformation programs.
Prior client-facing career experience in engagement management, consulting, or account leadership that informs growth conversations.

Responsibilities

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.
Break complex programs into manageable workstreams with clear ownership, sequencing, and dependencies.
Drive schedules from design through launch across multiple concurrent Agile teams, aligning delivery managers and product managers around an integrated plan.
Define program-level KPIs and governance, and use data to report health and guide decisions across scope, timeline, budget, and quality.
Translate customer needs into technical requirements linked to business outcomes, and facilitate architecture and engineering discussions to help guide technical direction.
Decompose complex technical problems into actionable solutions and contribute to technical documentation and program documentation standards.
Own the AI Development Life Cycle at the program level and set standards for Senior Delivery Managers to apply across workstreams.
Define program-wide completion standards for probabilistic and AI-driven features, including evaluation thresholds, human-in-the-loop checkpoints, and post-launch monitoring.
Partner with AI engineering leads on model risk, data readiness, evaluation strategy, and observability; translate uncertainty into a client-actionable program plan and risk register.
Define and report success measures for AI-augmented delivery, including quality, rework, review overhead, and velocity.
Assess whether agentic approaches suit client needs, considering context management, latency, infrastructure, and cost, and explain decisions to clients.
Use AI tools such as Claude to accelerate planning, specifications, reporting, and stakeholder communication, and model this use for delivery leaders.
Serve as a senior program partner to client executives and maintain trust through transparent, consistent communication.
Anticipate bottlenecks, manage escalations, and make trade-offs that balance business needs and technical constraints.
Lead trade-off decisions with customers, stakeholders, and partner teams when priorities conflict, and address misalignments that put outcomes or quality at risk.
Communicate schedules, progress, and business impact to stakeholders and senior leaders.
Partner with Client Partners on follow-on work and program expansion opportunities.
Lead and mentor Senior Delivery Managers and Delivery Managers, providing concrete feedback and stretch opportunities.
Create clarity for teams amid ambiguity and conflicting priorities, and contribute to the firm's delivery practice, tools, and frameworks.
Assess program staffing and capability gaps, and work with Client Partners and leadership on staffing needs and high-potential talent.
Conduct executive interviews and contribute to firm-wide go/no-go hiring decisions.