Senior Technical Program Manager at Pencil

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.

This is a craft role focused on rigour: the structure that keeps a fast-moving engineering team aligned, combined with enough technical depth to apply that rigour credibly in an AI-native, agent-driven environment.

Key Responsibilities

Operating Rhythm & Cadence

• Help establish the operating cadence for your area of the product and engineering organisation.
• Apply the minimum viable structure that keeps your 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.

Workback Planning & Dependency Management

• Own the workback plan and dependency map for programs in your portfolio — releases, integrations, 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.
• Maintain the trackers and visibility surfaces that let engineers, product managers, and stakeholders see the same state of the world — keeping 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 — so status is a link, not a meeting.
• Surface technical and timeline risk early, challenge optimistic plans, and enforce readiness gates before commitments are made externally.

Cross-Team Program Delivery

• Run end-to-end the programs that require multiple teams to move together — feature launches, integrations, and technical migrations.
• Scope, sequence, and drive these programs to delivery: own the schedule, the trade-offs, and the comms back to stakeholders.
• Manage the seams between teams — where product hands off to engineering, and where engineering hands off to another workstream.
• Resolve cross-team blockers directly, going lead-to-lead to clear dependencies so coordination doesn't need to escalate upward.

Risk, Escalation & Decision Support

• Apply 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.
• Translate engineering reality for non-technical stakeholders and back again, so no one is surprised by scope or timeline.
• Keep a clean view of your program portfolio for your manager and the wider TPM function — a one-pager when it's a one-pager moment, a full dependency map when it isn't.
• Produce a trustworthy weekly written status for stakeholders and leadership, giving visibility across your programs without requiring attendance at every meeting.

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.

Explicitly Not Owned

• People management, performance, growth, and hiring — stay with engineering leadership and team leads.
• Technical decisions and architecture — owned by engineering leadership.
• Priority and product direction — owned by Product Managers.

Your Background

• 6+ years of experience as a Technical Program Manager, ideally in AI/ML, platform infrastructure, or developer tooling.
• Track record running complex programs with multi-team dependencies and hard external deadlines.
• 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.
• 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, and the judgement to know which the situation calls for.
• Comfortable contributing to a young TPM discipline — helping shape templates, cadences, and norms rather than just inheriting them.
• 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

• 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 program.
• 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.
• Documentation and templates that outlast the individual — contributing to the cadences, formats, and trackers used across the TPM function.

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 EMEA.
• Enhanced parental leave policies, whether you become a parent through birth, adoption, or surrogacy.
• Access to our Pencil office in The Shard, London.
• Flexible working hours.