[Hiring] Technical Program Manager @Robots and Pencils

Role Description

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.

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.

Qualifications

• 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 applied-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.

Benefits

• Salary range: $202,589 CAD - $238,426 CAD or $191,226 - $219,746.
• Comprehensive package of benefits including paid time off, medical/dental/vision insurance, and 401(k) to eligible employees.