Head of Engineering

Come shape the future of education with us.

At Compass, we're on a mission to transform the school day for everyone - from staff and students to families and administrators. We build smart, seamless technology that empowers schools to focus on what really matters: learning, growing and thriving.

That mission has fuelled our growth into a global scale-up, now supporting 5,000+ schools across three countries, backed by a team of 300+ people. Our all-in-one school management platform is redefining how education communities connect, communicate and operate.

We're now looking for a Head of Engineering to own end-to-end engineering delivery and the day-to-day people leadership of our engineering org, spanning Compass, SchoolBytes, Griddle and Clipboard.

About the Role

Reporting to the CPTO, you'll translate technology and product priorities into predictable engineering execution, build and develop a strong Development Manager cohort, and own the engineering operating model, organisational capability and delivery performance.

This is a leadership role built around the Development Manager layer - you'll lead through 5-7 Development Managers rather than directly managing squads, and be accountable for the consistency, capability and execution of the wider engineering organisation of ~40-50 engineers.

What You'll Do

Engineering Delivery & Operations

• Own engineering's delivery performance across all squads, partnering with Product to ensure capacity, priorities and roadmap commitments are realistic, transparent and aligned.
• Establish a consistent engineering operating model, spanning planning, estimation and release practices, that enables teams to plan, prioritise and deliver predictably at scale.
• Own engineering capacity planning and allocation across squads, balancing strategic priorities, delivery commitments and team capability.
• Establish and monitor meaningful engineering performance metrics, covering roadmap predictability, cycle time, quality, reliability technical debt and team health and report on these to the CPTO and ELT.
• Identify delivery risks and dependencies early, driving resolution or escalating material trade-offs to the CPTO.

People Leadership

• Directly manage and develop the Development Manager cohort. Set clear expectations, coach on people leadership and hold them accountable for their squads' delivery and team health.
• Own engineering headcount planning, hiring and onboarding in partnership with the CPTO and People & Culture.
• Continuously assess engineering team structures, skills and capabilities to ensure the organisation is designed for current and future priorities.
• Build engineering career pathways and capability frameworks that support progression for engineers and managers.
• Own engineering engagement and retention, monitoring team health signals and championing a strong engineering culture.

Engineering Practice & Standards

• Partner with technical leaders (Development Managers, Tech Leads and the Head of Technology) to ensure engineering decisions support scalability, maintainability, security, reliability and delivery outcomes - you'll own engineering quality and technical execution even though this role is not the ultimate architecture owner.
• Champion consistent engineering standards, tooling and ways of working across squads.
• Balance delivery pace against technical debt and quality, escalating trade-offs to the CPTO where they affect strategy or architecture.
• Partner with the Head of Technology to ensure engineering teams implement and maintain required standards for reliability security and compliance across AU, UK and Ireland.

Stakeholder Partnership

• Act as engineering's day-to-day representative to Product, People & Culture, the Head of Technology and other functional leaders.
• Give the CPTO clear, timely visibility into delivery status, risks and people matters.

About You

This role is for an experienced engineering leader who's managed through managers across multiple teams in a product-led SaaS environment - someone who measures success by the strength of the team they've built, backed by strong delivery, people leadership and commercial judgement.

You will bring:

• Experience leading through engineering managers across multiple teams, with accountability for delivery, people and organisational performance.

• 10+ years experience in software engineering, including several years leading Engineering/Development Managers in a product or SaaS environment; the shape of that experience matters more than an exact number of years.
• A track record of owning delivery outcomes across multiple teams to squads, ideally in a product-led SaaS, PE-backed or similarly performance-oriented environment where predictability and efficiency are closely tracked.
• Experience scaling an engineering organisation and leading through change or transformation, including building consistent practice from process immaturity.
• Strong people leadership - experience coaching and developing engineering managers, not just individual engineers.
• Strong commercial and resource-management capability, comfortable owning capacity planning, headcount trade-offs and organisational design decisions.
• Ability to operate effectively with Product leadership, aligning delivery capacity and commitments against roadmap priorities.
• Experience using engineering metrics (delivery, quality, reliability, team health) to drive performance, not just report on it.
• Sufficient technical depth to engage credibly with Compass' engineering stack and technical leaders, and to understand trade-offs relating to scalability, maintainability, security and reliability.

Highly regarded:

• Experience across distributed or multi-entity engineering teams; AU/UK/Ireland exposure is a plus given Compass' footprint.
• Direct experience with C#/.NET, React.js, Node.js and Typescript.