Head of AI Strategy & Operations (12 Month Contract)

Come shape the future of education with us.

Compass is one of the world’s leading education technology platforms, trusted by more than 5,000 schools across Australia, the UK, and Ireland. As a high-growth scale-up backed by significant investment and a global mission, we’re on a mission to deliver integrated software solutions that simplify school operations and improve teaching, learning and engagement.

We’re seeking a Head of AI Strategy & Operations to design and deliver the internal AI capabilities that will reshape how Compass functions, from go-to-market and marketing to product velocity and cross-functional workflows.

This is initially a 12-month full-time contract role, with an opportunity for extension.

About the Role

In this role, you’ll work across Sales, Marketing, Product, Engineering, Support, and Leadership helping teams move faster, work smarter, and unlock leverage through automation and intelligent systems. You’ll also collaborate closely with our CPO, CRO, CTO, Security team, and AI Working Group to define and operationalise Compass’s internal AI roadmap.

This is an opportunity to architect and execute a company-wide AI strategy, starting internally - with scope to expand into customer-facing experiences as we build conviction.

You will also:

• Define and lead Compass’s internal AI roadmap, prioritising use cases that drive commercial efficiency, team enablement, and product acceleration.
• Identify inefficiencies across Sales, Marketing, Product, and Support, then prototype, test, and scale intelligent agents and AI-driven tools that materially improve internal velocity and decision-making.
• Work closely with business unit leaders to understand workflows, identify pain points and translate these into high-leverage AI opportunities.
• Evaluate and implement the right models, tools, APIs, and orchestration frameworks. Experience with vector databases and utilising RAG to enhance LLMs is a plus. You'll also work with vendors as necessary to achieve quantifiable business outcomes.
• Collaborate with our CTO and Security team to ensure internal tooling is safe, compliant, and robust.
• Establish frameworks, integrations, and architecture that will support future customer-facing AI features once internal systems are embedded.

About You

If you're a builder with strong strategic intuition, a technologist who understands business operations, and an operator who can deliver results, we’d love to hear from you.

You will also:

• Be a creative problem solver with an experimental, self-starting attitude.
• Have 1–3 years experience in RevOps, Sales Strategy, BizOps, or Automation roles, or equivalent experience, in tech-forward teams.
• Be comfortable with tools like Salesforce, Excel, SQL, and at least one automation platform (e.g., Make, Zapier, Retool, Relevance).
• Have basic Python or JavaScript skills; the ability to "vibe-code" is welcomed.
• Have passion for learning new technologies and applying them to solve real business problems.
• Be a strong collaborator who can work across technical and non-technical teams. You are commercially minded and able to communicate across functions with business stakeholders.
• Have the ability to clearly document processes, logic, and system interactions for others to follow.

Preferred Skills but Not Required

• Experience with LLMs, agent architectures, or prompt engineering.
• Familiarity with REST APIs and integrating third-party systems.
• Background in no-code/low-code platforms.
• Previous exposure to CRM or GTM tooling (e.g., Gong, Outreach, HubSpot).

What’s in it for you?

• We come together with our unique strengths to work towards a common purpose - shaping the future of education. When you join our team, you will collaborate with individuals who are passionate, driven, and open to embracing change in a fast-paced environment

• A flexible working environment - our teams work 3 days from our offices in Melbourne and Sydney!
• Learning & Development opportunities - we want you to grow and get the most out of your role!
• 24/7 access to our Employment Assistance Program (EAP) through the means of face-to-face, livechat and phone support.
• Meaningful Scope: Start by solving internal challenges, and help shape how AI drives value for our customers over time.

It is a really exciting time to join Compass. We are growing and are looking for ambitious individuals who want to grow alongside us. Compass is proud to be an equal opportunity employer. We embrace and celebrate diversity and are committed to creating an inclusive environment for all employees.

Prior To Commencing Employment, You Require:

• a valid Employee Working With Children Check
• a satisfactory National Police Check
• verification of unrestricted work rights in Australia, eg citizenship, passport, or birth certificate

Ready to make a difference?

Apply today and help us empower schools to focus on what matters most: teaching and learning.

Find out more about Compass on our website - .