Technical Program Manager

Robots & Pencils; United States; Remote; USD 140,000 - 190,000; Full time

Job summary

Robots & Pencils is seeking a Technical Program Manager to own end-to-end, multi-workstream AI, cloud, and enterprise transformation programs, translating client goals into technical plans and delivering measurable business value.

You will bridge business and engineering, facilitate architecture discussions, drive integrated planning across distributed teams, and define KPIs, governance, and risk management to keep programs on track and on budget.

Qualifications

• Experience leading large, multi-workstream AI, cloud, and digital transformation programs.
• Ability to translate client goals into technical plans and drive execution across teams.
• Strong ability to define KPIs, governance, and data-driven program health.

Responsibilities

• Own end-to-end delivery of large-scale AI/digital/cloud programs from strategy to value realization.
• Break down complex programs into deliverable workstreams with clear ownership.
• Drive program schedules across multiple Agile teams with aligned plans.
• Define program-level KPIs, governance, and risk management.

Skills

Program leadership

Agile delivery

Stakeholder management

Technical direction

AI enablement

Job description

Technical Program Manager

Remote in Canada or US

Company Overview

Robots & Pencils is an applied AI engineering firm building the next frontier of business architecture. We design and ship AI co-workers that integrate into enterprise operations and deliver measurable results for our clients. We're all in on AWS, combining deep UX capability with senior engineering talent to get AI into production fast and keep it there.
We’ve earned the trust of leaders across Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, and Manufacturing and more, and earned a reputation as the nimble alternative to traditional global systems integrators. Founded in 2009, with delivery centers in Canada, the United States, Eastern Europe, and Latin America, we are smaller, faster, and more senior by design. Our teams average 15+ years of experience. We move fast, sweat the details, and build things that actually ship.

Position Overview

As a Technical Program Manager, you own the full arc of large, multi-workstream programs, from translating a client’s business goals into a technical plan through launch and the value it delivers afterward. You sit at the intersection of business and engineering: facilitating architecture and engineering discussions, shaping technical direction alongside our engineering leads, and keeping multiple distributed teams moving toward the same outcome.

Why This Role Matters

The biggest engagements Robots and Pencils takes on are enterprise AI, cloud, and agentic transformations with many teams, many stakeholders, and real money on the line. Technical Program Managers are what keep those programs from fragmenting. You can sit with a client executive in the morning and an engineering lead in the afternoon and make sure both are working toward the same business result. When priorities conflict, or risk shows up with limited information and a tight deadline, you frame the trade-off clearly and drive the decision, so our promise of production-ready AI holds at enterprise scale.

What You’ll Do

Program Leadership

• 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
• Take large, complex programs and break them down into manageable, deliverable workstreams with clear ownership, sequencing, and dependencies
• Drive program schedules from design to launch across multiple concurrent Agile teams, keeping delivery managers and product managers aligned on one integrated plan
• Define program-level KPIs and governance, using data to report program health and guide decisions across scope, timeline, budget, and quality

Technical Direction

• Bridge business requirements and technical solutions, distilling customer needs into clear technical requirements and mapping each one back to the business outcome it serves
• Facilitate engineering and architecture discussions, and build a deep enough technical understanding of the products, across frontend and back-end technologies, to help drive the technical direction of the teams
• Decompose complex technical problems into actionable, deliverable solutions the teams can execute against
• Contribute to technical documentation and define the documentation standards your programs follow

AI Enablement

• Own the AI Development Life Cycle (AIDLC) at the program level, and set the standard Senior Delivery Managers follow for standing it up across workstreams
• Set the program-wide definition of done for probabilistic and AI-driven features (evaluation thresholds, human-in-the-loop checkpoints, post-launch monitoring) and hold every workstream to it
• Partner with AI engineering leads on model risk, data readiness, evaluation strategy, and observability for agentic work, and translate technical uncertainty into a program plan and risk register the client can act on
• Define what success looks like for AI-augmented delivery across the program (quality, rework, review overhead, and velocity, not just tests passed) and drive status visibility across complex AI-driven pipelines
• Make the call on when an agentic approach is the wrong tool for a client’s needs, weighing context management, latency, infrastructure, and cost, and defend that call to the client
• Use AI yourself every day, with tools like Claude, to accelerate planning, specifications, reporting, and stakeholder communication, and model that for the delivery leaders on your programs

Stakeholder Alignment & Communication

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