Technical Program Manager

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

Serve as the senior program partner to client executives, building trust through transparency, consistency, and clear communication

Anticipate bottlenecks before they land, provide escalation management, and make the trade-offs that balance business needs against technical constraints

Facilitate and lead trade-off decisions with customers, stakeholders, and partner teams when priorities conflict, and manage escalations or misalignments whenever committed outcomes or quality are at risk

Communicate program schedules, progress, and business impact to stakeholders and senior leaders, so executives see ongoing value, not just status

Partner with Client Partners to shape the follow-on work and expansion opportunities that grow out of the program

Leadership & Influence

Lead and mentor the Senior Delivery Managers and Delivery Managers on your programs with concrete feedback and stretch opportunities

Thrive in an innovative environment where ambiguity and conflicting priorities are the norm, and create clarity for the teams around you

Shape R&P’s delivery practice, tools, and frameworks beyond your own programs

Assess program staffing and capability gaps, and partner with Client Partners and leadership on staffing needs and high-potential talent

Conduct executive interviews and serve as an essential voice in go/no-go hiring decisions across the firm

What You’ll Bring

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 track record leading large-scale ($10M+) AI, digital, or cloud transformation programs from strategy through to realized business value

Practical application of frameworks (Well-Architected, Cloud Adoption Framework) to inform program decision-making and solution governance

Strong technical foundation: able to engage credibly on architecture, frontend and back-end technologies, and cloud-native design, and to decompose complex technical problems into deliverable solutions; ability to distill customer needs into technical requirements and functional specifications, map them to business outcomes

Track record leading programs where AI/ML or agentic capability was core to the solution, including how you managed model risk, evaluation, and client expectations, and the ability to set program-wide standards for evaluation, human-in-the-loop checkpoints, and monitoring

Demonstrable daily use of AI tools (e.g., Claude) to enhance planning, specifications, reporting, and documentation

Experience with delivery and engineering tooling (e.g., Jira, Confluence, GitHub, Azure DevOps, CI/CD pipelines)

Comfort operating in ambiguity, and the credibility with clients to bring growth conversations forward with Client Partners

Helpful Extras and Unique Skills

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 app0lied-AI initiatives in enterprise

Comprehensive knowledge of AWS services, architectures, and best practices, applied to guide technical decisions and strategic planning

Owned the end-to-end delivery of complex, multi-workstream agentic AI transformation programs

Prior career experience in client-facing roles (engagement manageme