Head of Engineering

Who we are:

WeSki is an innovative, passionate, and fast-moving product-led company. With over $100M in yearly sales, growing 2x year-on-year while remaining profitable, we are in a rapid growth mode. This unique position makes our business, product and engineering opportunities (and challenges) all the more exciting.

Our vision is to make it easy for skiers across the globe to book and enjoy their ideal ski trip at the best possible price. As the ultimate ski trip booking platform, WeSki enables everyone to design and book their ideal adventure in just a few clicks - quickly, seamlessly, and affordably. In an $80 billion industry that has remained largely traditional, this opens up a massive opportunity to redefine ski trips for modern consumers.

WeSki’s technology compares millions of combinations of flights, accommodation, transfers, passes, gear, and lessons instantly, saving hours of planning. Each trip is fully customisable, giving customers the flexibility of building it themselves, but with the expert protection and support of a holiday provider.

With all trip components automatically linked, customers can relax and enjoy their holiday knowing that all the logistics are taken care of - alongside 24/7 customer service whilst they’re away.

About the role:

We’re looking for an experienced, strategic, and hands-on Head of Engineering to build, lead, scale, and inspire our growing engineering organization.

You’ll take full ownership of our engineering vision, structure, and delivery - balancing startup agility with operational maturity as we move into our next growth phase.

What You Will Do

• Lead and scale WeSki’s engineering organization while building the structure, processes, and autonomy needed for our next growth phase.

• Develop and mentor engineering leads and future managers, helping them become strong, independent technical leaders.

• Hire and grow exceptional engineering talent, establishing scalable systems for onboarding, performance, and growth.

• Drive technical excellence across all disciplines - backend, frontend and DevOps - ensuring scalability, reliability, and maintainability of our platform.

• Shape the architecture of a complex, API-driven travel platform that integrates hundreds of suppliers and serves millions of dynamic trip combinations in real time.

• Own delivery performance - ensuring clarity of priorities, predictable execution, and accountability for results.

• Champion AI-driven productivity, embedding tools and workflows that enhance code quality, velocity, and developer experience.

• Own and continuously improve Developer Experience (DevEx) - from local environments to deployment pipelines - ensuring engineers can move fast with confidence and focus on impact.

• Collaborate cross-functionally with Product, Data, and CS to ensure that engineering decisions drive measurable business outcomes and user value.

• Partner closely with the CTO and co-founders on long-term technical strategy, org design, and capacity planning.

• Stay close to the code - review, guide, and set technical direction while empowering teams to execute with autonomy and confidence.

Requirements:

• 7+ years of experience in software engineering, including 3+ years in leadership roles (Engineering Team Lead / Group Manager / R&D Manager).

• Proven success leading teams and in a fast-paced, product-driven startup.

• Experience scaling engineering organizations while maintaining speed, quality, and team spirit.

• Track record of hiring, mentoring, and developing high-performing teams.

• Broad technical understanding - backend (Node.js, TypeScript), frontend (React, Next.js, TypeScript), DevOps, and architecture for scalable systems.

• Tech-savvy mindset and enthusiasm for integrating AI tools to boost developer velocity and code quality.

• Excellent communication skills and ability to influence across functions.

• Strategic thinker with strong execution instincts and empathy for both people and process.

• Skier or Snowboarder - Always a plus