About the role

Lead Technical Program Manager coordinating AI-powered advertising platform releases, integrations and migrations at Pencil. Owning Tier 1 client engineering commitments, dependencies and delivery across product and engineering teams.

Responsibilities

Own engineering-request programs for Tier 1 clients, including intake, scoping, prioritisation input, sequencing and delivery tracking.
Translate client needs into buildable requirements and communicate engineering constraints back to client-facing teams.
Enforce readiness gates and maintain a trusted view of client commitments, owners and statuses.
Design and run operating cadences across product and engineering teams.
Support sprint planning, standups, retrospectives and demos; coordinate larger retrospectives when needed.
Own workback plans, dependency maps and standing operational views for releases, integrations, client commitments and cross-team engineering work.
Maintain trustworthy project-management tooling, automate status collection and reporting, and lead adoption of new tools and AI-native workflows.
Run multi-team programs including feature launches, client integrations and technical migrations.
Manage cross-team dependencies, resolve blockers and independently address drifting programs.
Apply escalation frameworks, own first-response coverage for incidents and client interruptions, and advise on complex delivery decisions.
Produce weekly written status updates for stakeholders and leadership.
Support OKR reporting and tracking for engineering and product leads.
Create TPM templates, cadences and trackers; mentor junior program managers and participate in TPM hiring interviews.
Stay current with AI-native engineering delivery practices and bring relevant ideas to Pencil.

8+ years of experience as a Technical Program Manager, ideally in AI/ML, platform infrastructure, or developer tooling.
Track record 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 a system architecture and understanding the implications; comfortable in conversations about APIs, integration design, and platform trade-offs without being the engineer in the room.
Engineering background is a strong plus.
Structured thinker who writes clean documents and produces clear framing with a recommended path.
Strong communication across leadership, technical and client-facing audiences, with judgement about the appropriate level of detail.
Experience mentoring other program managers and creating templates, cadences and norms for a TPM discipline.
Track record of introducing tools or ways of working that measurably reduced overhead.
Bonus: experience in a high-growth scale-up and/or a company building infrastructure while using it on real customer workloads.
Must work from a home country within Canada, the US or LATAM, with regular working-hours overlap with London-based teams.

25 days PTO plus public holidays, although we operate a Flexible Time Off scheme.
Health insurance / private medical cover.
Monthly stipend towards wellness, fitness, and learning and development.
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.