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Lead Technical Program Manager - Remote

USAPosted 21 Oct 2026

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About this role

At Pencil, we are building the operating system for AI-powered marketing — a SaaS platform that uses Generative AI to redefine how the world's biggest brands plan, produce and deploy advertising. Our mission is to make AI the default in marketing without replacing creative people. To do that at the pace we're moving, our product and engineering teams have to move together without losing coherence. That is the work this role leads.

The Lead Technical Program Manager independently owns a portfolio of complex, cross-team programs that have a direct impact on the company: platform releases, integrations, technical migrations, and the engineering commitments we make to our most important clients. It sets the workback plans, dependency maps and operating cadence for those programs, and increasingly defines the methods and processes other program managers use.

A core part of this role is supporting the engineering requests and requirements of our Tier 1 clients. You will be the program owner who turns what our largest enterprise customers need into scoped, sequenced engineering work and who makes sure what we commit to them is realistic, tracked, and delivered. This is a senior craft role. It doesn't own a product area and doesn't manage engineers directly. What it owns is rigour (the structure that keeps a fast-moving engineering team aligned) combined with the technical depth and judgement to apply that rigour credibly in an AI-native, agent-driven environment, and to help others in the TPM function do the same.

This role reports into the Principal Technical Program Manager and partners closely with engineering leads, product managers and client-facing teams. Remote, based in Canada, the US or LATAM, with regular working-hours overlap with our London-based teams. KEY 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.

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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.

GOAL TRACKING - 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. YOUR BACKGROUND - 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. BENEFITS - 25 days PTO plus public holidays, although we operate a Flexible Time Off scheme. - Health insurance / private medical cover.

Source listing: ashby_pencil

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