Technical Program Manager

Robots and Pencils•New York, NY

10d•$180,000 - $215,000•Hybrid

About The Position

Robots & Pencils is hiring a Technical Program Manager to own the full lifecycle of large, multi-workstream programs, translating client business goals into technical plans and leading delivery through launch and realized business value. The role operates at the intersection of business and engineering, facilitating architecture and engineering discussions, shaping technical direction with engineering leads, and aligning distributed teams around shared outcomes. Programs include enterprise AI, cloud, and digital transformations, often involving multiple teams, stakeholders, and significant budgets. The Technical Program Manager leads programs from strategy and roadmap through launch, establishes integrated plans across concurrent Agile teams, and sets program-level governance, KPIs, and standards. The role also owns program-level AI Development Life Cycle practices, including standards for evaluating AI-driven features, human-in-the-loop checkpoints, model risk, data readiness, observability, and post-launch monitoring. The position requires regular use of AI tools to accelerate delivery activities and sound judgment about when agentic approaches are appropriate. This role serves as a senior partner to client executives, manages trade-offs and escalations, communicates progress and business impact, and partners with Client Partners on follow-on opportunities. It also mentors delivery managers, contributes to the firm’s delivery practice and frameworks, assesses staffing needs, and participates in hiring decisions. The role is based on-site three days a week in New York City or Mountain View, California, and requires approximately 20% client travel.

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.
Proven experience 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 and translate customer needs into technical requirements and functional specifications tied to business outcomes.
Experience leading programs where AI/ML or agentic capabilities were core to the solution, including management of model risk, evaluation, and client expectations.
Ability to establish 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 advance growth conversations alongside Client Partners.

Nice To Haves

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

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 concurrent Agile teams and maintain an integrated plan with delivery managers and product managers.
Define program-level KPIs and governance, report program health, and guide decisions about scope, timeline, budget, and quality.
Translate customer needs into technical requirements and connect requirements to business outcomes.
Facilitate engineering and architecture discussions and help guide technical direction across frontend and back-end technologies.
Decompose complex technical problems into actionable solutions teams can deliver.
Contribute to technical documentation and establish documentation standards for programs.
Own the AI Development Life Cycle at the program level and set standards for Senior Delivery Managers implementing it across workstreams.
Define program-wide completion standards for 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, and translate uncertainty into actionable plans and risk registers.
Define and report success measures for AI-augmented delivery, including quality, rework, review overhead, and velocity.
Assess when an agentic approach is unsuitable, considering context management, latency, infrastructure, and cost, and explain the decision to clients.
Use AI tools such as Claude in day-to-day planning, specifications, reporting, and stakeholder communication, and model their use for delivery leaders.
Serve as a senior program partner to client executives and build trust through transparent, consistent communication.
Anticipate bottlenecks, manage escalations, and balance business needs against technical constraints.
Lead trade-off decisions with clients, stakeholders, and partner teams, and address misalignments when outcomes or quality are 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 through feedback and stretch opportunities.
Create clarity for teams in an innovative environment with ambiguity and conflicting priorities.
Help shape the company’s delivery practice, tools, and frameworks beyond assigned programs.
Assess staffing and capability gaps and partner with Client Partners and leadership on staffing needs and talent.
Conduct executive interviews and contribute to hiring go/no-go decisions.