Head of Sales

About WeSki Disrupting the traditional $80 billion ski travel industry with the world's first self-service platform for booking an entire ski trip in just a few clicks. Using our unique dynamic package technology, WeSki empowers customers to plan, compare, book and fully customize their ski holiday by providing real-time prices and availability for millions of ski trip combinations. WeSki's technology connects to thousands of suppliers to provide customers with a one-stop-shop solution to book everything they need for their ski holiday, including flights, airport transfers, accommodations, ski lift passes, ski gear rental, and more. Once skiers are on their trip, WeSki's technology continues to provide a stress-free experience by coordinating all trip components, so skiers can relax and enjoy their ski holiday without worrying about the logistics. WeSki partners with over a hundred ski resorts (and counting) across 10 different countries and already sold over 40,000 ski holiday packages to skiers worldwide.

WeSki

The hassle-free way to plan, compare and book the perfect ski trip 🏔. Click. Click. Booked. ⛷️🏂

Travel TechDynamic Holiday PackagingSki HolidaysOnline Travel AgencyOnline Tour Operatorand Snowboarding Holidays

See all employees

W

weski.com

51-200 employees

Software Development

London

Privately Held

7.7k LinkedIn followers

Raised $4.1M

• 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.

Required

• 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.

Preferred

• 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.