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Pencil is building an AI-powered marketing operating system—a SaaS platform that uses generative AI to help the world's biggest brands plan, produce, and deploy advertising. The company's mission is to make AI the default in marketing without replacing creative people.
As Lead Technical Program Manager, you will independently own a portfolio of complex, cross-team programs with direct company impact: platform releases, integrations, technical migrations, and engineering commitments to Tier 1 clients. You will set workback plans, dependency maps, and operating cadence for these programs, and increasingly define the methods and processes other program managers use.
This is a senior individual contributor role focused on rigour and technical depth. You do not manage engineers directly or own a product area. Instead, you own the structure that keeps a fast-moving engineering team aligned, combined with the technical judgment to apply that rigour credibly in an AI-native, agent-driven environment.
Key responsibilities include:
**Tier 1 Client Engineering Requests**: Own the full lifecycle of engineering requests from Tier 1 clients—intake, scoping, prioritization, 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 clients so commitments are realistic. Enforce readiness gates before dates or scope are committed, and maintain a single trusted view of every open client commitment.
**Operating Rhythm & Cadence**: Design and run the operating cadence for your area, applying minimum viable structure that keeps teams aligned without slowing them down. Ensure decisions get made on time with the right people in the room and a written trail of what was decided and why.
**Workback Planning & Dependency Management**: Own workback plans and dependency maps for programs in your portfolio. Hold the full picture when others are heads-down: what depends on what, who owns what, what is about to slip, and what needs escalation. Keep your project management tool trustworthy so status can be read without verbal check-ins. Actively reduce complexity through automation and new tools.
**Cross-Team Program Delivery**: Independently run programs requiring multiple teams to move together, including those with company-level impact. Determine methods and approach for new or ambiguous programs. Manage seams between teams and resolve cross-team blockers directly, lead-to-lead.
**Risk, Escalation & Decision Support**: Apply and refine escalation frameworks. Own the first-responder rota for incidents and client interrupts. Provide expert advice on complex delivery decisions. Produce trustworthy weekly written status for stakeholders and leadership.
**Goal Tracking**: Support engineering and product leads on OKR reporting and tracking.
**Growing the TPM Function**: Create templates, cadences, and trackers used across the TPM function. Mentor more junior program managers. Act as an ambassador for company values in how programs are run and in TPM hiring.
You will report into the Principal Technical Program Manager and partner closely with engineering leads, product managers, and client-facing teams. The role is remote, based in Canada, the US, or LATAM, with regular working-hours overlap with London-based teams.
**Requirements**
- 8+ years of experience as a Technical Program Manager, ideally in AI/ML, platform infrastructure, or developer tooling
- Track record of independently running complex programs with multi-team dependencies, hard external deadlines, and company-level impact
- 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 system architecture and understanding implications; comfortable in conversations about APIs, integration design, and platform trade-offs without being the engineer in the room
- Engineering background a strong plus
- Structured thinker who writes clean documents: takes ambiguity, incomplete specs, and competing stakeholder views and produces clear framing with a recommended path
- Communication at every altitude: crisp updates for leadership, detailed dependency maps for tech leads, clear status for client-facing teams, with judgment to know which the situation calls for
- Experience mentoring other program managers and creating templates, cadences, and norms a young TPM discipline runs on
- Track record of bringing in new tools or ways of working that measurably reduced overhead for teams around you
- Bonus: experience in a high-growth scale-up and/or experience in a company building infrastructure while simultaneously using it on real customer workloads
