Head of Sales

Who We Are



WeSki is a self-service ski trip booking platform built for the modern traveller. Our vision is simple: to make great ski experiences available to everyone. We enable customers to build and book a fully custom ski holiday in minutes, combining flights, accommodation, transfers, ski passes, equipment and lessons in one seamless flow.

Behind the scenes, our technology evaluates millions of trip combinations in real time. We dynamically connect inventory from 1,500+ suppliers, automatically optimise which components we bundle together, and present only options that really work. What used to take hours of research and coordination now takes a few clicks and finds much better results for our customers.

Every trip is fully customisable. Customers get the flexibility of building it themselves, with the security, protection, and support of a regulated holiday provider. Each trip is dynamically orchestrated in real time, with dependencies automatically managed across suppliers at scale, spanning over 300 resorts in 20+ countries across Europe, North America, Asia and Oceania. From booking to return, we manage the entire journey, so customers can relax and enjoy their holiday.

We’re about to cross $170M in annual sales. Growth is accelerating, unit economics are strong, and the business funds its own growth. High transaction volume, complex infrastructure, real impact, delivered by a small, high-performing team.

We operate in a ~$100B global ski travel market with no technology-native market leader. The industry is still dominated by traditional tour operators, with business models and infrastructure that have barely evolved in decades. This is a rare opportunity to define the future of ski travel at global scale.

Role Overview



We are building a dedicated sales function at WeSki, and we are looking for the person to lead it. Many of our customers are happy to plan and book independently through our platform. Others want to talk to someone who genuinely knows the resorts, understands what makes a family ski holiday work, and can help them make confident decisions. This role exists to serve that second group properly.

The profile we are looking for is specific: an excellent travel professional who is also a genuine skiing expert. You need to bring both to the table, because our customers are trusting us with the trip they save up for all year, and that trust is built in the first few minutes of a conversation.

This is a founding leadership position. You will design the sales process end to end, define how success is measured, build and coach the team, and own the results. In the first season you will also sell personally: this is a hands-on role, not a purely managerial one. As the function proves itself, you will grow the team and hire into it.

The role reports into Customer Experience and works closely with Growth, Operations and Product. It is fully remote, with a strong focus on the UK and European markets. A deep understanding of the UK consumer travel market is essential.

Key Responsibilities:



• Build the function. Design the sales process from first contact through to a booked holiday, including how enquiries are prioritised, how conversations are managed, and how a booking is handed over to our operations team.

• Set the strategy. Define how we sell, to whom, and through which channels, and adapt it as the market and our product evolve.

• Own the numbers. Define the KPIs for the team, monitor performance against them, and report on results to senior leadership.

• Sell. Handle customer conversations directly, particularly in the early months. You will set the standard by demonstrating it.

• Lead and develop the team. Coach the current team, raise the level of consultative selling across it, and create the structure a growing team needs.

• Validate and improve. Test approaches, measure what works, and iterate. We would rather learn quickly than commit to assumptions.

• Shape the tooling. Work with Product and Technology to build the systems and automation the team needs, so that time is spent with customers rather than on admin.

• Lead AI adoption. Identify where AI can improve the sales process and implement AI-powered tools and workflows across the function. Experiment with new capabilities, measure their impact, and continuously improve how the team uses AI to sell more effectively and operate more efficiently.

• Work across the business. Partner with Growth on the flow and quality of enquiries, and with Operations to ensure what we promise during a sale is delivered on the ground.

• Recruit and onboard. As the function scales, identify, hire and develop the people who will join it.

• Represent the customer. You will hear what customers want before anyone else. Bring that back and help shape the product.

• 6+ years of experience in sales leadership, including managing, coaching, and developing sales teams.
• Genuine skiing expertise. You ski, you know European resorts first hand, and you can tell a customer which mountain suits their family and which does not. This is not a preference. A customer planning their one big trip of the year can tell within a sentence whether they are talking to someone who has actually been there.

• A background in travel, as a travel agent, tour operator or equivalent. You have planned and sold real trips for real people, and you understand what goes into a holiday beyond the price: the connections, the transfers, the things that go wrong and how to prevent them.

• Proven experience selling high-value, considered purchases to UK consumers in a consultative, advice-led way mixed with strong business acumen.

• Deep understanding of the UK consumer travel or leisure market, including how UK customers research and buy.

• Experience building a sales process or function from scratch, or substantially rebuilding an existing one. This role has no existing playbook to inherit.

• Comfort owning a target and being measured against it, and the data literacy to define sensible metrics and interpret them honestly.

• Excellent written & verbal communication skills in English. A large share of customer conversations happen in writing, and clarity and warmth on the page matter as much as they do on the phone.

• Self-direction and strong organization. This is a remote role with significant autonomy and broad ownership.

• Comfort using AI and automation tools as part of everyday work.

• Flexibility during our peak booking period, including weekend availability as needed. Ski travel is a highly seasonal business and the busiest months are demanding.

Advantages (Not Mandatory):

• Ski instructor, ski guide, seasonaire or resort-side experience.
• Background in travel technology as well as traditional travel.
• Experience working in a seasonal business.
• Experience hiring and onboarding into a growing team.
• Proficiency in French or other European languages.