Jobs at WeSki (Now Hiring) — 2 open

Who we are

WeSki is a self-service ski trip booking platform built for the modern traveler. Our vision is simple: make great ski experiences available to everyone. Customers 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 optimize 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 delivers better results.

Every trip is fully customizable. Customers build it themselves with the security and support of a regulated holiday provider. Behind every booking, dependencies across suppliers are orchestrated in real time, at scale, spanning 384 resorts in 20 countries across Europe, North America, Asia, and Oceania.

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

The role

We're looking for WeSki's first ever Head of Brand & Creative to be the senior creative, content, and brand leader at WeSki.

You'll own creative direction and shape the voice and messaging of everything we put in front of customers — and build the brand strategy that makes it consistently excellent. From paid creative to lifecycle CRM to in-product experiences, you're the quality bar. Your job is to turn a great product into a brand that skiers genuinely love and talk about.

You'll be expected to drive the creative and content function independently, from strategy through to delivery, with a high degree of autonomy and end-to-end ownership.

Why this role

• Category creation, not category maintenance. The $100B ski travel market has no technology-native brand leader. You won't be polishing the 14th iteration of someone else's identity. You'll define what a modern ski brand looks like.
• Real product behind the brand. WeSki actually delivers what most travel brands only claim to. Millions of dynamically packaged trips, real-time orchestration across thousands of suppliers, 317 resorts. The story sells itself if you can tell it.
• Profitable and growing fast. $100M in annual sales, EBITDA positive, self-funded growth. You're building a brand on top of a real business, not a hype curve.
• Direct line to leadership. You report to the VP Growth and partner directly with the CEO on brand direction. No layers, no internal politics, no waiting in line.
• End-to-end creative ownership. Strategy, positioning, creative direction, content, copy, production. The full picture. No piece is outside your remit.
• An audience that actually cares. Skiers and snowboarders aren't passive consumers. They have taste, identity, and tribal loyalty. A brand built for them can become beloved in a way few travel brands ever are.

What you'll do

Brand, creative, content, and messaging (your primary mandate)

• Set and own the creative direction for all paid, lifecycle, and organic communications — from the brief to the final asset. This is the heart of the role.
• Own the creative production process and resources. Whether doing it yourself, working with agencies, freelancers, or other formats - you set the brief, push the quality bar, and own the output
• Build WeSki's brand strategy, positioning, tone of voice, and visual identity across all channels, partnering with WeSki's management team on long-term direction
• Build the content architecture across the full customer journey: messaging hierarchies, frameworks, and templates that scale across channels, segments, and seasons
• Write and oversee all customer-facing copy: campaign headlines, landing pages, emails, push notifications, social posts, UI microcopy, CS interactions
• Identify and develop brand opportunities: collaborations, events, in-trip experiences, partnerships that strengthen our market position
• Evolve the brand book as WeSki scales into new channels, markets, and use cases

CRM content and strategy

• Own the messaging, content, and strategic direction of all CRM and lifecycle communications. What we say in every email, SMS, push, and WhatsApp, and to whom
• Set strategic direction: what audiences to target, what journeys to build, what outcomes to optimize for
• Review and approve all CRM campaigns for tone, clarity, creative quality, and brand alignment before launch
• Use CRM performance data (open rates, click-through, revenue attribution) to inform content and creative decisions
• Own the CRM content calendar

Organic channels 

• Own organic social strategy and content calendar
• Manage ad-hoc marketing projects

Requirements

• 8-10+ years in brand marketing, creative strategy, or content leadership, ideally at a consumer or travel brand
• Skier or snowboarder, we don’t judge as long as you love the snow
• Proven creative direction and art direction experience, with the portfolio to back it up. You've shaped campaigns, built brand identities, and owned creative production at a senior level
• Exceptional writing and editorial skills, with native English level. You set the tone of voice standard and can write across formats, from a 3-word CTA to a full email sequence
• Strategic thinking about how brand, creative, and content drive commercial outcomes. You connect brand activity to revenue, retention, and LTV
• Experience building long-term brand strategies: positioning, brand architecture, competitive differentiation. Not just executing campaigns
• Familiarity with CRM tools (HubSpot, Braze, Klaviyo, or similar) and a clear understanding of how lifecycle marketing works
• Experience developing content architecture across multiple channels and customer journey stages
• Comfort with data and insight. You use performance metrics to inform creative and content decisions
• The drive and confidence to work with high autonomy and execute end to end with minimal hand-holding
• The ability to balance creative vision with commercial accountability. You care about both brand equity and business results
• Comfort building from scratch in a fast-moving environment. You create structure, process, and creative systems while things are still in motion
• Proactive use of AI tools to scale content production, automate versioning and localization, and increase creative velocity without sacrificing quality

Not mandatory, but a strong plus

• Experience in travel, lifestyle, or experience-led categories
• Experience scaling a brand through a growth phase. You've built the playbook, not just inherited one