Senior Software Engineer – AI Discovery Team

At On the Beach, we’re redefining how millions of customers discover, plan and book their holidays. Our platform sits at the heart of that experience and we’re now investing in the next frontier: AI-driven travel discovery.

We’re forming a new AI Discovery team. A small, senior led group with a mandate to explore and shape the future of how customers search, discover and plan their trips.

This is not a traditional product team.

It’s an innovation-focused environment where experienced engineers lead ideas end-to-end, from concept through to real world validation working directly on problems that could redefine the customer experience.

As a Senior Software Engineer in the AI Discovery team, you’ll work at the frontier of applied AI building and testing new product experiences with real customers.

You’ll focus on rapid experimentation and intelligent prototyping, exploring areas such as:

• Conversational trip planning
• AI-powered personalisation and recommendations
• New search and discovery paradigms using LLMs
• Agent based and workflow-driven experiences

This role is about learning fast and building the right things, not just building things right.

You’ll collaborate closely with product managers, designers, analysts and researchers to design experiments, validate ideas and identify which opportunities are worth scaling into full product capabilities.

You’ll work on AI-driven problems that reach real customers, not just internal demos, with the autonomy to explore ideas in a low-process, high-trust environment.

This is a role where you’ll help shape product direction as much as implementation, while influencing how AI is adopted across the organisation. You’ll be part of a small, experienced team focused on solving meaningful problems and driving real impact.

This is an opportunity to work at the intersection of AI, product, and customer experience, contributing to how a well-established travel platform continues to evolve with new technologies.

If you enjoy exploring new ideas, experimenting with emerging tools, and building solutions that can influence product direction, we’d love to hear from you!

• Design and build lean, high-impact prototypes to test hypotheses with real customers
• Run multiple experiments each quarter using approaches like fake-door tests, rapid prototypes and beta releases
• Explore and apply modern AI capabilities, including LLMs, retrieval systems and recommendation techniques
• Work across the full stack: from backend services and APIs to frontend experiences
• Collaborate with cross-functional partners to design experiments that maximise learning
• Iterate quickly based on qualitative and quantitative feedback
• Partner with existing product teams when experimenting in their domains
• Contribute to internal tooling, patterns and approaches that accelerate AI adoption across engineering
• Balance speed and pragmatism, knowing when to move fast and when to invest in robustness

We’re looking for experienced engineers who are comfortable operating in ambiguous, fast-moving environments and enjoy solving new types of problems.

• Strong full-stack engineering skills, with the ability to ship working software quickly
• Experience working with modern AI/ML tools or APIs (e.g. LLMs, OpenAI, Anthropic, Bedrock or similar)
• A track record of working in ambiguous problem spaces and driving ideas forward
• The ability to make pragmatic technical decisions with incomplete information
• Experience building prototypes, MVPs, or working in innovation focused environments
• A strong product mindset (you care about customer impact, not just technical elegance!)
• Confidence communicating ideas and trade-offs to both technical and non-technical stakeholders
• A collaborative approach and the ability to work effectively across team boundaries

• Experience validating product ideas through experimentation (A/B testing, user research, etc.)
• Exposure to recommendation systems, search or personalisation problems
• Experience contributing to technical direction or mentoring…