Lead Technical Program Manager - Remote

Role overview

Client engineering delivery

• Own intake, scoping, prioritization input, sequencing, and delivery tracking for Tier 1 client engineering requests.
• Translate client needs into buildable requirements and communicate engineering realities to keep commitments realistic.
• Enforce readiness gates and maintain a trusted view of client commitments, owners, and status.
• Surface conflicts between client requests and roadmap work early, with a recommended trade-off.

Program operations and delivery

• Design and run operating cadences, coordinate timely decisions, and maintain written decision records.
• Support sprint planning, standups, retrospectives, and demos; coordinate larger retrospectives when appropriate.
• Own workback plans, dependency maps, schedules, and status views for releases, integrations, and cross-team programs.
• Run complex programs independently, resolve cross-team blockers, and manage handoffs between product, engineering, and client-facing teams.
• Identify and communicate delivery risks, challenge optimistic plans, and apply escalation frameworks.
• Automate reporting and tracker hygiene, and lead adoption of useful tools and AI-native workflows.
• Support OKR tracking and produce trustworthy written status for stakeholders and leadership.

TPM function development

• Create templates, cadences, and trackers for use across the TPM function.
• Mentor and support junior program managers and coordinate shared program activities.
• Participate in TPM hiring interviews and stay current with delivery practices in AI-native engineering organizations.

Background and qualifications

• 8+ years as a Technical Program Manager, ideally in AI/ML, platform infrastructure, or developer tooling.
• Track record independently delivering complex, multi-team programs with hard external deadlines and company-level impact.
• Experience owning engineering delivery for enterprise or Tier 1 clients and setting realistic commitments.
• Technical fluency in system architecture, APIs, integration design, and platform trade-offs.
• Engineering background is a strong plus.
• Ability to structure ambiguity and communicate clearly across leadership, technical, client, and client-facing audiences.
• Experience mentoring program managers, building TPM practices, and introducing tools or methods that reduce overhead.
• High-growth scale-up experience, or infrastructure-building experience alongside real customer workloads, is a bonus.

Work arrangement

• Remote work from the employee’s home country in Canada, the US, or LATAM.
• Regular working-hours overlap with London-based teams; flexible working hours are offered.

Benefits

• 25 days of PTO plus public holidays, with a Flexible Time Off scheme.
• Health insurance or private medical cover.
• Monthly wellness, fitness, and learning and development stipend.
• Enhanced parental leave and access to the Pencil office in The Shard, London.

About Pencil