Remote in Canada or US

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. We move fast, sweat the details, and build things that actually ship.

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.

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.

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

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

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

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

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

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

Jira, Confluence, GitHub, Azure DevOps, CI/CD pipelines)

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 management, consulting, account leadership) that informs growth conversations

The AI landscape changes weekly. You're senior enough to know better and curious enough to keep learning anyway.

You ship exceptional, not perfect, and you don't put your name on work you wouldn't stand behind.

An employee's position within the salary range will be based on several factors including, but not limited to, relevant education, qualifications, certifications, experience, skills, seniority, geographic location, performance, shift, travel requirements, sales or revenue-based metrics, any collective bargaining agreements, and business or organizational needs. The salary range for this role is $202,589 CAD - $238,426 CAD or $191,226 - $219,746. We offer a comprehensive package of benefits including paid time off, medical/dental/vision insurance and 401(k) to eligible employees.

An offer of employment may be conditional upon successful completion of a background check in accordance with local legislation and our candidate privacy notice. Employment decisions are based upon job-related reasons regardless of an applicant's race, color, religion, sex, sexual orientation, gender identity, age, national origin, disability, marital status, genetic information, protected veteran status, or any other status protected by law.

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📌 Technical Program Manager (Remote) (Ottawa)
🏢 Robots and Pencils
📍 Ottawa