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. That is the work this role leads.

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. It sets the workback plans, dependency maps and operating cadence for those programs, and increasingly defines the methods and processes other program managers use.

A core part of this role is supporting the engineering requests and requirements of our Tier 1 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.





Key Responsibilities Tier 1 Client Engineering Requests

Own the program for engineering requests and requirements coming from our Tier 1 clients: intake, scoping, prioritisation input, sequencing and delivery tracking.

Partner with client-facing teams, product managers and engineering leads to translate client needs into clear, buildable requirements — and translate engineering reality back to the client side so commitments are realistic.

Enforce readiness gates before any date or scope is committed to a Tier 1 client, and keep a single trusted view of every open client commitment, its owner and its status.

Anticipate where client demands will collide with roadmap work and surface the trade-off early, with a recommended path, rather than letting it land as an escalation.

Operating Rhythm & Cadence

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.

Apply the minimum viable structure that keeps teams aligned without slowing them down: enough ceremony to make decisions stick, never more.

Ensure decisions get made on time, with the right people in the room, and with a written trail of what was decided and why.

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

Own the workback plans and dependency maps for the programs in your portfolio — releases, integrations, client commitments and cross-team engineering work.

Hold the full picture for your programs when everyone else is heads-down: what depends on what, who owns what, what is about to slip, and what needs to be escalated.

Keep your project management tool (e.g. Linear) trustworthy enough that its views can be read without a verbal check: issues correctly labelled, estimated, assigned and in the right state.

Own the standing views the organisation relies on — production bugs, in-flight work, blocked items, client commitments — so status is a link, not a meeting.

Actively reduce complexity: automate status collection, reporting and tracker hygiene wherever possible, and lead adoption of recent 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.

Cross-Team Program Delivery

Independently run the programs that require multiple teams to move together — feature launches, client integrations and technical migrations — including those with company-level impact.

Determine the methods and approach for new or ambiguous programs: scope, sequence and drive them to delivery, owning the schedule, the trade-offs and the comms back to stakeholders.

Manage the seams between teams — where product hands off to engineering, engineering hands off to another workstream, and client-facing tea

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