At Pencil, we are building the operating system for AI-powered marketing — a SaaS platform that uses Generative AI to redefine how the world's biggest brands plan, produce and deploy advertising. Our mission is to make AI the default in marketing without replacing creative people. To do that at the pace we're moving, our product and engineering teams have to move together without losing coherence. The Lead Technical Program Manager independently owns a portfolio of complex, cross-team programs that have a direct impact on the company: platform releases, integrations, technical migrations, and the engineering commitments we make to our most important clients. You will be the program owner who turns what our largest enterprise customers need into scoped, sequenced engineering work and who makes sure what we commit to them is realistic, tracked, and delivered. This is a senior craft role. It doesn't own a product area and doesn't manage engineers directly. What it owns is rigour (the structure that keeps a fast-moving engineering team aligned) combined with the technical depth and judgement to apply that rigour credibly in an AI-native, agent-driven environment, and to help others in the TPM function do the same. This role reports into the Principal Technical Program Manager and partners closely with engineering leads, product managers and client-facing teams. Remote, based in Canada, the US or LATAM, with regular working-hours overlap with our London-based teams. Design and run the operating cadence for your area of the product and engineering organisation, and help shape the cadence used across the wider TPM function. Support (not own) the recurring sprint rhythm — planning, standups, retros and demos — and coordinate larger retrospectives across teams when a program or incident calls for one. Workback Planning & Dependency Management Keep your project management tool (e.g. Actively reduce complexity: automate status collection, reporting and tracker hygiene wherever possible, and lead adoption of new tools and AI-native workflows that make the function faster. Surface technical and timeline risk early, challenge optimistic plans, and enforce readiness gates before commitments are made externally. Independently run the programs that require multiple teams to move together — feature launches, client integrations and technical migrations — including those with company-level impact. Manage the seams between teams — where product hands off to engineering, engineering hands off to another workstream, and client-facing teams hand off to delivery. Put out fires before they cause harm: spot the program that is drifting and act on it independently. Risk, Escalation & Decision Support Apply and refine the escalation framework: flag what is on track, what is at risk, and what needs a leadership call — and make sure the right call gets made. Own the first-responder rota for incidents and client interrupts in your area, absorbing and routing them before they land on a team mid-flow. Translate engineering reality for non-technical stakeholders and back again, so no one is surprised by scope or timeline. Stay current with how leading AI-native engineering organisations run delivery, and bring the best ideas back to Pencil. People management, performance, growth, and hiring decisions — stay with engineering leadership and team leads. Technical decisions and architecture — owned by engineering leadership. Priority and product direction — owned by Product Managers. The commercial client relationship — owned by client-facing teams; this role owns the engineering delivery behind it. 8+ years of experience as a Technical Program Manager, ideally in AI/ML, platform infrastructure, or developer tooling. ~ Experience owning engineering delivery for enterprise or Tier 1 clients: managing their requests, setting realistic commitments, and keeping them informed without over-promising. ~ Genuine technical fluency: comfortable reading a system architecture and understanding the implications; Bonus: experience in a high-growth scale-up, and/or experience in a company building infrastructure while simultaneously using it on real customer workloads. Tier 1 client engineering commitments are delivered on time, with risks raised to client-facing teams before dates slip, not after. An operating rhythm for your area that runs on time, with explicit inputs and decisions out — measured by stakeholder satisfaction and meeting hygiene. On-time delivery of the cross-functional programs in your portfolio, with material risks raised before they become crises. Reduction in escalations reaching senior leadership that should have been resolved within your programs. 25 days PTO plus public holidays, although we operate a Flexible Time Off scheme. ~ Health insurance / private medical cover. ~ Remote — work from anywhere in your home country within Canada, the US or LATAM. ~ Enhanced parental leave polic

📌 Lead Technical Program Manager (Canada)
🏢 Pencil
📍 Canada