Job Description

Who we are



WeSki just hit a record-breaking milestone: over $100M in revenue in the last year, including a $1M single day.

We’re building momentum fast, and we’re doing it by making ski travel radically easier to discover, plan, and book.

We’re operating in a massive opportunity the total addressable market is ~$80B, and we believe we’re still early in unlocking it.

WeSki is a self-service ski trip booking platform that lets customers build and book a full trip in a few clicks, comparing options across flights, accommodations, transfers, ski passes, gear, and lessons, and then customizing what they want. The platform connects trip components automatically, with customer support available throughout the journey.

WeSki is looking for a Senior Product Designer to take end-to-end ownership over key product experiences across web applications + AI agent, and to lead our design system hands-on

You’ll be the primary (and for now, solo) Product Designer in the company, reporting to the Head of Product, owning outcomes end-to-end and partnering closely closely with Product, Engineering, and Growth to ship high-quality experiences that help skiers explore, plan, and book trips confidently, and keep improving them after launch with iteration, experimentation, and user feedback.

You’ll thrive here if you love craft and outcomes at scale: you care about pixels and prototypes, but also about funnels, clarity, conversion, and building repeatable systems that help a team move fast without breaking consistency.

What you’ll do

• Lead product design end-to-end, from ideation to production.
• Influence product strategy bring customer insights to shape priorities, define opportunities, and inform roadmap decisions.
• Partner deeply with Product + Engineering to define problems, explore solutions, and ship measurable improvements.
• Level up our design system components, patterns, guidelines, tokens, and governance - so we build faster with consistency.
• Use AI tools thoughtfully to accelerate ideation, exploration, QA, content, and workflow - without compromising quality.
• Lead UX research (usability testing, interviews, concept tests, prototype tests), and translate insights into shipped product improvements.
• Contribute to design culture and methodology (critiques, principles, decision logs, process templates), especially important in a lean team.

What you’ll need

• High internal motivation: you love product design, are curious, and take pride in outcomes.
• Comfort operating as a solo/primary designer in an organization - strong collaboration, prioritization, and communication skills.
• Process-oriented thinking: you can structure ambiguity, run end-to-end UX processes, and choose the right fidelity at the right time.
• Hands-on experience with usability testing and translating findings into iteration.
• Experience with A/B testing, data-driven design and knowledge of SEO practices.
• Strong Figma skills (components, variants, auto-layout, prototyping) and a portfolio that demonstrates craft + impact.

Requirements

• 5+ years of product design experience shipping modern digital products.
• Meaningful experience designing for web applications, turning complex exploration and itinerary planning into friendly experiences.
• Meaningful experience in B2C (or B2SB / prosumer) products at scale - designing for large user bases, conversion funnels, and iterative growth.
• Proven experience working with design systems and contributing to their evolution.

Bonus points

• You’re a skiing/snowboarding fanatic (or at least deeply into the culture and customer mindset).
• You’ve managed or mentored other designers (even informally).
• You’ve shipped or designed AI-driven product experiences (agents, copilots, recommendations, personalization).
• Experience in travel, marketplaces, booking engines, pricing, or dynamic packaging.