Head of Customer Service

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 thousands of 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 the users.

Every trip is fully customizable. 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 315 resorts in 21 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’ve recently crossed $100M in annual sales, including a $1M single day. 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 ~$80B global ski 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:

At WeSki, Customer Service is not a support function - it is a core business engine. As our Head of Customer Service, you will lead one of the most critical, high-impact teams in the company: the group responsible for customer trust, operational excellence, and real-time problem solving during peak season.

This role sits at the intersection of leadership, judgment, and execution. You will manage a global CS organization operating across multiple time zones, handling high-stakes, on-trip issues while scaling quality, structure, and accountability.

You will work closely with Operations, Product, and Leadership to ensure the CS team is not only performing on KPIs, but also operating with clarity, professionalism, and strong managerial standards.

This role requires a rare combination of empathy, decisiveness, and sharp commercial judgment - especially in moments

Key Responsibilities:

• Lead and manage the Customer Service organization (20+ representatives across multiple regions and time zones).
• Own customer experience outcomes across all stages: pre-trip, on-trip, and post-trip.
• Build a structured, accountable team operating model with clear reporting lines, ownership, and escalation paths.
• Ensure operational readiness ahead of each season, including staffing plans, training, tooling, and playbooks.
• Drive onboarding and continuous training programs with measurable knowledge validation and performance tracking.
• Maintain strong cross-functional alignment with Operations to ensure smooth resolution of supplier and fulfillment issues.
• Set and enforce high standards of managerial integrity, professionalism, and internal communication
• Own decision-making in sensitive, high-cost customer cases, demonstrating strong commercial judgment and discretion.
• Develop scalable processes to improve efficiency, reduce friction, and prevent recurring customer issues.
• Monitor and improve key service metrics (CSAT, response times, cost per case, resolution quality), while ensuring they reflect true operational health.
• Act as the senior leadership voice of the CS team, ensuring trust, clarity, and stability during high-pressure periods.

Requirements:

• 6+ years of experience in Customer Service leadership in a B2C environment (mandatory).
• Proven experience managing multi-layer teams (including team leads and global coverage).
• Strong track record of building structure, accountability, and performance systems - not just “keeping things running.”
• Hands-on experience implementing and scaling Customer Service infrastructure, including CRM systems, ticketing platforms, workflows, automation, and reporting tools.
• Hands-on experience with leading Customer Service platforms such as HubSpot, Intercom, and Front - including ownership of implementation, optimization, and cross-functional integration.
• Strong advantage for candidates who have implemented AI-driven solutions in Customer Service environments, including automation, AI agents, intent classification, knowledge-based response systems, or workflow orchestration - with measurable impact on efficiency or cost.
• Experience building or significantly upgrading CS operational foundations (process design, escalation frameworks, QA systems, knowledge bases, SLAs).
• Exceptional judgment in customer-facing decisions involving financial exposure, precedent-setting, or reputational risk.
• High integrity and professionalism, with the ability to operate as a trusted senior leader.
• Experience working in fast-paced, high-growth environments; startup experience is a strong advantage.
• Strong communication skills - direct, clear, and aligned with leadership standards.
• Ability to lead through pressure, ambiguity, and peak-season intensity.
• Data-driven mindset with the ability to translate metrics into operational action.
• Native English speaker. Additional languages are a plus.

Advantages:

• Background in travel-tech, marketplaces, or operationally complex consumer products.
• Experience supporting global customers in real-time, high-stakes environments.
• Ski industry familiarity or passion for winter travel - always a plus.