Head of Engineering

At Pencil, we are driving innovation in advertising technology through our state-of-the-art SaaS product, which harnesses Generative AI to redefine content creation. Our mission is to make AI the default in advertising without replacing creative people. To achieve this, we need to make sure that our technology isn’t just in the hands of big brands - we need to try to help small businesses and creative individuals too. You will lead Pencil’s core platform engineering organisation to deliver a high-performing, reliable, and scalable platform that powers our customers’ marketing workflows. You will set the technical direction, elevate engineering excellence, and enable teams to build fast, secure, and high-quality products that deeply integrate into customers’ day-to-day journeys. Key responsibilities: Leadership & OrganisationLead and grow a high-performing engineering organisation across multiple teams.Build a culture of technical excellence, ownership, psychological safety, and continuous improvement.Develop the engineering leadership bench through coaching, mentorship, and clear career pathways.Partner closely with Product, Design and GTM to align engineering delivery with business strategy and customer impact.Oversee hiring, onboarding, and career development for all engineers.Build diverse, high-trust teams capable of delivering ambitious technical outcomes.Create clarity through consistent communication, performance expectations, and feedback. Technical Direction & Execution:Define and drive the long-term technical strategy, architectural roadmap, and platform evolution.Provide technical oversight across systems, integrations, infrastructure, and data flows.Stay hands-on enough to support teams with architectural decisions, unblock complex challenges, and maintain a deep understanding of the codebase.Ensure engineering practices (CI/CD, testing, observability, reliability, security) scale with the company. Delivery, Projects & Prioritisation: Own the engineering delivery operating model: sprint rituals, planning, estimation, and cross-functional alignment.Ensure predictable, transparent, and outcome-driven delivery across all engineering squads.Identify risks early, remove blockers, and drive continuous improvement in velocity and quality. Platform Reliability, Performance & Security: Ensure the platform meets high standards for reliability, performance, and responsiveness.Implement strategies for scalability, fault tolerance, and incident reduction.Partner with Information Security to maintain SOC2 Type 2 controls and embed security-by-design across engineering.Oversee SLAs/SLOs, incident response, root-cause analysis, and preventive improvements. Your background:12+ years of industry experience, including senior engineering leadership in a fast-paced tech environment in Enterprise SaaS. Strong experience with building HTML editing workflows is a specific plus. Any experience in GenAI, creative or advertising industries would be beneficial.Proven experience managing multiple engineering teams and managers, whilst still staying close to the day to day of the Engineering team.Knowledge of Python, Typescript, multiple types of databases and asynchronous event driven architectures.Experience scaling engineering organisations, processes, and platforms.Prior exposure to SOC2 Type 2 compliance or similar security frameworks is a plus.Excellent communicator able to bridge technical and business priorities. You’ll Thrive Here If You Are…Fast: You bias to action, remove blockers quickly, and help teams ship value early and often.Human: You lead with empathy, build trust, and create an environment where engineers do their best work.Surprising: You challenge assumptions, think creatively, and introduce better ways to solve problems.Owner: You take responsibility for outcomes (not just output), and you empower teams to do the same.Simple: You cut through complexity and guide teams toward clear, scalable, maintainable solutions. KPIs & Success MeasuresPredictable delivery: % of sprints completed as planned, lead time, cycle time.Platform reliability: uptime, incident frequency, mean time to recovery (MTTR).Code quality: reduction in bugs, test coverage, and velocity improvements.Engineering engagement scores and retention of high performers.Manager effectiveness indicators across engineering.Delivery of major platform milestones/roadmap items. Benefits:25 days PTO plus public holidays, although we operate a Flexible Time Off schemeHealth insurance / private medical coverMonthly stipend towards wellness, fitness, and learning and developmentRemote - work from anywhere in your home countryEnhanced parental leave policies, whether you become a parent through birth, adoption or surrogacyAccess to our Pencil office in The Shard, London for UK employeesFlexible working hours