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 transparent 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 policies, whether you become a parent through birth, adoption or surrogacy. ~ Access to our Pencil office in The Shard, London, when you're there. ~ Flexible working hours. Pencil uses AI to make ads. Our mission is to make marketing effective and effortless.

We want to become the default way ads get made — because AI ads are faster and cheaper to make, and better performing, than making them without AI. We're called Pencil because we believe AI will be a tool for creative people, not a replacement — it may even be as fundamental a tool in the future as the pencil was in the past. Pencil was founded in 2018 with a team from Google, Facebook and Uber with backing from Sequoia and Entrepreneur First.

The Brandtech

Group's mission is to be the best company in the world at helping leading global brands drive growth by connecting content, data and media using technology. It was founded in June 2015 (as You & Mr Jones), with a simple mission to help brands do their marketing better, faster and cheaper using technology. It was renamed The Brandtech Group in January 2022.

Today it generates more than $1BN in revenue and is a leading global digital content partner for many of the world's biggest brands and companies, often using its unique in-housing model. Clients include Banco Itau, Danone, Google, Intuit, LVMH, Microsoft, Morgan Stanley, Netflix, Reckitt, Renault-Nissan, PayPal, TikTok, Uber and Unilever. #

📌 Lead Technical Program Manager - Remote (Toronto)
🏢 Pencil
📍 Toronto