pencil - Lead Technical Program Manager - Remote
Requirements
• 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 a strong plus — many of the best program managers we've worked with came up through engineering before moving into the discipline. • Structured thinker who writes clean documents: takes ambiguity, incomplete specs and competing stakeholder views and produces a clear framing with a recommended path. • Communication at every altitude: a crisp update for leadership, a detailed dependency map for a tech lead, a clear status for a client-facing team, and the judgement to know which the situation calls for. • Experience mentoring other program managers and creating the templates, cadences and norms a young TPM discipline runs on. • A track record of bringing in new tools or ways of working that measurably reduced overhead for the 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. • KPIS & SUCCESS MEASURES • Tier 1 client engineering commitments are delivered on time, with risks raised to client-facing teams before dates slip, not after. • Every open Tier 1 client request has a named owner, a status and a realistic date that can be read from a single view. • An operating rhythm for your area that runs on time, with clear inputs and decisions out — measured by stakeholder satisfaction and meeting hygiene. • Workback plans and dependency maps that exist, are current, and are trusted by the people they describe — measured by usage and reduction in unplanned slippage. • On-time delivery of the cross-functional programs in your portfolio, with material risks raised before they become crises. • Reduction in escalations reaching senior leadership that should have been resolved within your programs. • Team leads escalate delivery blockers to you, not upward — and client interrupts hit a named first responder, not whoever is nearest the code. • A trustworthy weekly status exists without leadership having to assemble it themselves. • New processes, templates and automations you created are adopted beyond your own programs and used across the TPM function. • More junior program managers you mentor grow measurably in scope and independence.
Responsibilities
• TIER 1 CLIENT ENGINEERING REQUESTS • Own the program for engineering requests and requirements coming from our Tier 1 clients: intake, scoping, prioritisation input, 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 the client side so commitments are realistic. • Enforce readiness gates before any date or scope is committed to a Tier 1 client, and keep a single trusted view of every open client commitment, its owner and its status. • Anticipate where client demands will collide with roadmap work and surface the trade-off early, with a recommended path, rather than letting it land as an escalation. • OPERATING RHYTHM & CADENCE • Design and run the operating cadence for your area of the product and engineering organisation, and help shape the cadence used across the wider TPM function. • Apply the minimum viable structure that keeps teams aligned without slowing them down: enough ceremony to make decisions stick, never more. • Ensure decisions get made on time, with the right people in the room, and with a written trail of what was decided and why. • Support (not own) the recurring sprint rhythm — planning, standups, retros and demos — and coordinate larger retrospectives across teams when a program or incident calls for one. • WORKBACK PLANNING & DEPENDENCY MANAGEMENT • Own the workback plans and dependency maps for the programs in your portfolio — releases, integrations, client commitments and cross-team engineering work. • Hold the full picture for your programs when everyone else is heads-down: what depends on what, who owns what, what is about to slip, and what needs to be escalated. • Keep your project management tool (e.g. Linear) trustworthy enough that its views can be read without a verbal check: issues correctly labelled, estimated, assigned and in the right state. • Own the standing views the organisation relies on — production bugs, in-flight work, blocked items, client commitments — so status is a link, not a meeting. • Actively reduce complexity: automate status collection, reporting and tracker hygiene wherever possible, and lead adoption of new tools and AI-native workflows that make the function faster. • Surface technical and timeline risk early, challenge optimistic plans, and enforce readiness gates before commitments are made externally. • CROSS-TEAM PROGRAM DELIVERY • Independently run the programs that require multiple teams to move together — feature launches, client integrations and technical migrations — including those with company-level impact. • Determine the methods and approach for new or ambiguous programs: scope, sequence and drive them to delivery, owning the schedule, the trade-offs and the comms back to stakeholders. • Manage the seams between teams — where product hands off to engineering, engineering hands off to another workstream, and client-facing teams hand off to delivery. • Resolve cross-team blockers directly, going lead-to-lead to clear dependencies so coordination doesn't need to escalate upward. • Put out fires before they cause harm: spot the program that is drifting and act on it independently. • RISK, ESCALATION & DECISION SUPPORT • Apply and refine the escalation framework: flag what is on track, what is at risk, and what needs a leadership call — and make sure the right call gets made. • Own the first-responder rota for incidents and client interrupts in your area, absorbing and routing them before they land on a team mid-flow. • Provide expert advice on complex delivery decisions that affect other teams or the company at large. • Translate engineering reality for non-technical stakeholders and back again, so no one is surprised by scope or timeline. • Produce a trustworthy weekly written status for stakeholders and leadership — a one-pager when it's a one-pager moment, a full dependency map when it isn't. • Support engineering and product leads on OKR reporting and tracking: keeping objectives and key results current, surfacing progress and drift each cycle, and turning them into a readable rollup so goal health is visible without a separate chase. • GROWING THE TPM FUNCTION • Create, not just improve, the templates, cadences and trackers used across the TPM function, and make sure they outlast you. • Mentor and actively support more junior program managers, and coordinate their activities on shared programs where needed. • Act as an ambassador for our values in how programs are run and in TPM hiring, including taking part in interview loops. • Stay current with how leading AI-native engineering organisations run delivery, and bring the best ideas back to Pencil. • EXPLICITLY NOT OWNED • People management, performance, growth, and hiring decisions — stay with engineering leadership and team leads. • Technical decisions and architecture — owned by engineering leadership. • Priority and product direction — owned by Product Managers. • The commercial client relationship — owned by client-facing teams; this role owns the engineering delivery behind it.
Benefits
• 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.
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