Lead Technical Program Manager - Remote

Pencil

2d • Remote

About The Position

Pencil is hiring a Lead Technical Program Manager to own a portfolio of complex, cross-team programs spanning platform releases, integrations, technical migrations, and engineering commitments to Tier 1 clients. The role establishes workback plans, dependency maps, delivery tracking, and operating cadences, and helps define the methods and processes used across the TPM function.

A central focus is owning the engineering delivery program for requests from Tier 1 clients: translating customer needs into scoped, sequenced engineering work, ensuring commitments are realistic, and maintaining a trusted view of status, ownership, and dates. The role independently coordinates programs involving multiple teams, manages dependencies and risks, supports decision-making and incident response, and communicates delivery status to technical and non-technical stakeholders.

This is a senior individual-contributor craft role. It does not own a product area or directly manage engineers. It reports to the Principal Technical Program Manager and partners with engineering leads, product managers, and client-facing teams. The position is remote for candidates based in Canada, the US, or LATAM, with regular working-hours overlap with London-based teams.

Requirements

• At least 8 years of experience as a Technical Program Manager, ideally in AI/ML, platform infrastructure, or developer tooling.
• Demonstrated ability to independently run complex programs with multi-team dependencies, hard external deadlines, and company-level impact.
• Experience owning engineering delivery for enterprise or Tier 1 clients, including managing requests, setting realistic commitments, and providing updates without over-promising.
• Technical fluency, including the ability to read system architecture and understand implications, and to discuss APIs, integration design, and platform trade-offs without serving as the engineer.
• Ability to structure ambiguity, incomplete specifications, and competing stakeholder perspectives into clear written framing and a recommended path.
• Strong communication skills across audiences, from leadership updates to technical dependency maps and client-facing status.
• Experience mentoring other program managers and creating templates, cadences, and norms for a developing TPM discipline.
• A track record of introducing tools or working practices that measurably reduce overhead for surrounding teams.

Nice To Haves

• Engineering background.
• Experience in a high-growth scale-up.
• Experience at a company building infrastructure while simultaneously using it on real customer workloads.

Responsibilities

• Own intake, scoping, prioritisation input, sequencing, and delivery tracking for engineering requests and requirements from Tier 1 clients.
• Translate client needs into clear, buildable requirements with product managers and engineering leads, and communicate engineering constraints so client commitments remain realistic.
• Enforce readiness gates before committing dates or scope to Tier 1 clients, and maintain a trusted view of open commitments, owners, and statuses.
• Anticipate conflicts between client demands and roadmap work, surface trade-offs early, and recommend a path forward.
• Design and run the operating cadence for the assigned product and engineering area, and help shape cadence across the TPM function.
• Ensure decisions are made on time with the right participants and maintain a written record of decisions and rationale.
• Support recurring sprint activities, including planning, standups, retrospectives, and demos, and coordinate larger retrospectives when needed.
• Own workback plans and dependency maps for releases, integrations, client commitments, and cross-team engineering work.
• Track program dependencies, ownership, schedule risks, potential slippage, and escalation needs.
• Maintain trustworthy project management tools and organizational views for production bugs, in-flight work, blocked items, and client commitments.
• Automate status collection, reporting, and tracker maintenance where possible, and lead adoption of new tools and AI-native workflows.
• Surface technical and timeline risks early, challenge optimistic plans, and enforce readiness gates before external commitments.
• Independently deliver cross-team programs, including feature launches, client integrations, technical migrations, and programs with company-level impact.
• Determine scope, sequencing, methods, and approach for new or ambiguous programs; own schedules, trade-offs, and stakeholder communications.
• Manage handoffs and coordination across product, engineering, workstreams, client-facing teams, and delivery.
• Resolve cross-team blockers directly with team leads and independently intervene when programs drift.
• Apply and refine escalation frameworks, identify when leadership decisions are needed, and ensure appropriate decisions are made.
• Own the first-responder rota for incidents and client interrupts in the assigned area, routing issues before they disrupt teams.
• Advise on complex delivery decisions affecting other teams or the company.
• Translate engineering constraints and delivery status for non-technical stakeholders and communicate stakeholder needs back to engineering.
• Produce trustworthy weekly written stakeholder and leadership status updates, using the appropriate level of detail.
• Support engineering and product leads with OKR reporting and tracking, surfacing progress and drift and producing readable rollups.
• Create templates, cadences, and trackers for use across the TPM function and ensure they remain useful beyond the programs the role directly owns.
• Mentor and support more junior program managers and coordinate their activities on shared programs when needed.
• Represent Pencil's values in program delivery and TPM hiring, including participating in interview loops.
• Stay current on delivery practices at AI-native engineering organisations and bring useful ideas to Pencil.

Benefits

• 25 days of PTO plus public holidays; the company operates a Flexible Time Off scheme.
• Health insurance / private medical cover.
• Monthly stipend toward wellness, fitness, and learning and development.
• Enhanced parental leave policies for becoming a parent through birth, adoption, or surrogacy.
• Access to the Pencil office in The Shard, London.
• Flexible working hours.
• Remote work from anywhere in the employee's home country within Canada, the US, or LATAM.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed