Lead Technical Program Manager

This is a fully remote position, open to applicants in United States, +1 more country.

📋 Description

• Take ownership of engineering-request programs for Tier 1 clients, encompassing intake, scoping, prioritization input, sequencing, and delivery tracking.

• Transform client requirements into actionable specifications and relay engineering limitations back to client-facing teams.

• Implement readiness gates and uphold a reliable overview of client commitments, responsible parties, and project statuses.

• Design and facilitate operating cadences across product and engineering teams.

• Assist in sprint planning, standups, retrospectives, and demos; coordinate larger retrospectives as necessary.

• Manage workback plans, dependency maps, and ongoing operational views for releases, integrations, client commitments, and cross-team engineering efforts.

• Maintain reliable project management tools, automate status collection and reporting, and spearhead the adoption of new tools and AI-driven workflows.

• Oversee multi-team programs, including feature launches, client integrations, and technical migrations.

• Manage dependencies between teams, resolve obstacles, and independently tackle programs at risk of drifting.

• Implement escalation frameworks, oversee first-response coverage for incidents and client interruptions, and provide guidance on complex delivery decisions.

• Generate weekly written status updates for stakeholders and leadership.

• Assist with OKR reporting and tracking for engineering and product leaders.

• Develop TPM templates, cadences, and trackers; mentor junior program managers and engage in TPM hiring interviews.

• Stay updated with AI-driven engineering delivery practices and propose relevant ideas to Pencil.

⛳️ Requirements

• A minimum of 8 years of experience as a Technical Program Manager, preferably in AI/ML, platform infrastructure, or developer tooling.

• Proven ability to independently manage complex programs with multi-team dependencies, strict external deadlines, and significant company-level impact.

• Experience in overseeing engineering delivery for enterprise or Tier 1 clients: managing their requests, setting realistic expectations, and keeping them informed without over-promising.

• Authentic technical fluency: adept at reading system architecture and understanding implications; comfortable engaging in discussions about APIs, integration design, and platform trade-offs without being the engineer present.

• An engineering background is a considerable advantage.

• A structured thinker who produces clear documents and offers well-framed recommendations.

• Excellent communication skills across leadership, technical, and client-facing audiences, with discernment regarding the appropriate level of detail.

• Experience mentoring fellow program managers and establishing templates, cadences, and norms for TPM practices.

• Proven history of implementing tools or methodologies that measurably reduced overhead.

• Bonus: experience in a high-growth scale-up and/or a company building infrastructure while utilizing it on real customer workloads.

• Must reside in a home country within Canada, the US, or LATAM, with regular working hours overlap with London-based teams.

🏝️ Benefits

• 25 days of PTO in addition to public holidays, although we operate under a Flexible Time Off scheme.

• Health insurance/private medical coverage.

• Monthly stipend for wellness, fitness, and learning and development.

• Remote work — operate from anywhere within your home country in Canada, the US, or LATAM.

• Enhanced parental leave policies applicable whether you become a parent through birth, adoption, or surrogacy.

• Access to our Pencil office located in The Shard, London, during your visits.

• Flexible working hours.