Director of Engineering

We’re looking for someone to lead the software engineering behind a national education platform, opening up curriculum data and safe AI to support brilliant teaching in every classroom. Oak is a fully remote, mission-driven organisation offering high levels of flexibility, autonomy, and purpose. We’re a national not-for-profit organisation working in partnership with teachers to create high-quality, sequenced curriculum and lesson resources for pupils across all subjects and age groups.

Our culture has been independently recognised through:

• Flexa verified (93% overall score, including 95% for working hours and 97% for role modelling)
• Escape the City's Top 1% Employers – based on anonymous colleague reviews of culture, development, and impact
• Investors in People Gold - through external accreditation and colleague feedback

About the Role

Oak is entering a critical new phase. Over the next three years, we will support the implementation of a revised national curriculum, deepen adoption of our digital products across schools, and play a leading role in shaping the safe and ethical use of AI in education. We are now seeking a Director of Engineering to lead the technology that underpins this work. This is a senior leadership role with responsibility for Oak’s engineering strategy, technical architecture and platform delivery.

You will lead engineering teams to build and operate reliable, secure and scalable systems that support teachers at scale and enable innovation across the education sector. You’ll work closely with product, design, data, teachers and content leaders to ensure our technology choices are grounded in real classroom needs, strong pedagogy and value for money, while also pushing forward what’s possible with the latest approaches and tools. You’ll empower teams to get solutions built and products and features shipped.

We welcome applications from candidates with senior engineering leadership experience across technology, digital or public service environments, including those who have not previously worked in education. If you’re excited by the challenge of building dependable systems that quietly do the heavy lifting for teachers, and shaping how safe AI is used across the sector, we’d love to hear from you.

What You’ll Be Doing

• Develop and manage a high performing Engineering department, leveraging internal and/or external relationships
• Manage the Engineering department budget (minimum of 6-figures)
• Accountable for the department's delivery against division and organisation-wide KPIs.
• Set and lead Oak’s technical direction, ensuring secure, scalable and high-performing platforms aligned with organisational and product priorities and public sector digital standards.
• Oversee software engineering, architecture, embedding engineering excellence, operational reliability, strong SDLC practice and continuous improvement, and ensuring compliance with relevant digital, security and data standards (including GDS and GDPR).
• Lead the implementation of data-intensive and emerging technologies (including AI/ML), ensuring production-ready systems and compliance with Oak’s technical and safety requirements.
• Member of the Senior Leadership Team.
• Lead the strategy and planning and model the culture of the organisation.
• Work in cross-functional and product-oriented squads with colleagues from across the organisation, as required.
• Deputise for the CEO and take on other general responsibilities as required.

3+ years’ experience overseeing engineering or technical capabilities of a department or division. Experience of being part of a senior or wider leadership team. Experience of recruiting, developing and managing a high performing department. Experience of managing a 6-figure budget and ensuring value for money. Extensive experience delivering secure, scalable, high-quality digital services in production environments. Experience implementing and operating data-intensive or emerging technologies (e.g., AI/ML), ensuring safe, reliable and responsible deployment. Experience leading the evolution of engineering systems over time, including evaluating new technologies, scaling cloud-based services, and ensuring high availability, CI/CD maturity and long-term platform resilience. Experience having deployed production ready AI technology (desirable).

You will be comfortable working at pace, with a range of digital systems (including proprietary ones as required) and you will continuously look at ways that the team can keep getting better. You will be excellent at working as part of a remote team, building relationships and managing your time effectively.

25 days annual leave, plus one extra day for each year of service (up to 28). Additional Oak closure days over Christmas/New Year. 11% employer pension contribution (with no minimum employee contribution). A 36-hour working week, with half-days on Fridays or every other Friday off. Fully remote working — we’ll support your home set-up and offer coworking options if preferred. Twice-yearly in-person offsites to collaborate, connect, and have fun. A culture that genuinely supports flexibility, autonomy, and trust.

Inclusion and Belonging

We believe diverse teams build better products. We warmly welcome applicants from all backgrounds, particularly those who are underrepresented in the tech and education sectors. We use the Applied recruitment platform to help reduce bias in our hiring process.

Location: Remote, but you must be based in the UK with the legal right to work here. Sponsorship: Unfortunately, we’re unable to offer visa sponsorship at this time. Closing date: 23:59 on Wednesday, 4 February 2026. We’ll be reviewing applications as they come in, and may close the role early.

If this sounds like the kind of role and team where you could do your life’s best work, we’d love to hear from you. We aim to run a fair, inclusive process that helps people show what they can really do.

Stage 1: Apply (via Applied) You’ll apply through the Applied platform. Your application will be scored anonymously against the published criteria and reviewed by more than one assessor.

Stage 2: Short practical exercise (video) If you progress, we’ll send you a short brief and a few suggested technologies you could use. You’ll then have time to go away, create a simple prototype or generate an insight in response to the brief, and record a short video walking us through what you have produced and why. For this role, we will be looking for evidence of technical judgement and engineering thinking, for example, how you approach system design, reliability, security, data or AI safety, rather than production quality or polished demos. The exercise is designed to be accessible to candidates who lead engineering teams and may not code day to day. Videos will be scored by a small group of assessors using clear criteria.

Stage 3: Interview A shortlist of candidates will be invited to a competency-based interview, assessed against the criteria set out in the job description. We’ll share full details, timelines and support as you progress. We’re happy to make reasonable adjustments at any stage.

Use of AI in applications You can use AI to help draft your answers, but remember, we are looking for your experiences and insights, not generic or AI-generated responses. We score for specific, real examples and your own judgement. If your answers read like AI output or could describe anyone’s experience, they will score poorly. We are receiving excellent responses to our job advertisements. This may lead us to close the role early, so if you are considering applying, then please get your application in early to avoid missing out.