• Drive execution across a large, complex portfolio of Health & Benefits products, ensuring delivery against key development priorities • Own and manage product initiatives end-to-end, from discovery through delivery, with a strong focus on measurable outcomes • Modernize existing products and contribute to building scalable, platform-driven solutions that improve customer and developer experiences • Translate complex business needs into actionable product requirements, including user stories and backlog prioritization • Partner closely with engineering, design, analytics, and business stakeholders to deliver high-impact solutions • Work within Agile frameworks, actively contributing to sprint planning, refinement, demos, and delivery processes • Engage in technical discussions to help shape architecture decisions and ensure alignment with platform capabilities (e.g., APIs, integrations) • Manage multiple initiatives across varying levels of complexity and maturity, balancing speed with quality • Use qualitative and quantitative data to inform decisions, measure success, and continuously iterate on product improvements • Contribute to reducing customer attrition risk by improving product usability, efficiency, and value delivery • Operate effectively in a fast-paced environment with rapid turnaround and high visibility across teams

• Own the digital customer journey. Map how industrial buyers discover, evaluate, configure, and purchase products across our portfolio of B2B brands. Identify where digital experiences are broken, missing, or could be transformative. • Design and deliver new digital capabilities. Product configurators, self-service portals, guided selling experiences, quote-to-order automation, personalized content journeys. You go from insight to prototype to shipped product — working directly in the tools, not just in requirements documents. • Run growth experiments and measure impact. Define hypotheses, design tests, set success criteria, and close the loop from idea to delivery to measured results. You own the experimentation framework and help the team build a culture of data-driven decision-making. • Bring new ideas to the business. You don't wait for stakeholders to ask for things. You proactively identify what customers need before internal teams do — using data, industry trends, and direct customer insight to push the business forward. • Work cross-functionally across brands. You are the connective tissue between the central digital team and brand-level marketing and sales teams. You bring shared capabilities to local execution and bring local customer insights back to the central product roadmap.

The Role: Leading small group adventures around the globe. The Commitment: Per-trip. Perfect for your vacation days or freelance life. Location: Anywhere but an office. The World! 🌍 Our Vision: Connecting People, Cultures, and Stories. This is why we exist. At WeRoad, we don’t just book flights; we bridge worlds. We’re on a mission to kill the digital disconnect and get people back into the real world. We take groups of strangers and turn them into a "wolfpack" through shared experiences and a bit of grit. After building a community of 5,000+ leaders in Europe, we’re finally launching in the States. (Watch the video to feel the energy of the Global Community) What is a WeRoad Group Leader? First things first: This is not a desk job. It’s also not a full-time career. It’s a passion project for people who live to travel. You keep your 9-to-5, your freelance hustle, or your creative grind. When you’re ready to escape, you pick a WeRoad trip and lead it. - You are on the ground: You’ll be physically on the trip—navigating the streets of Tokyo, hiking in Iceland, or catching sunsets in Baja with a group of 10-15 travelers. - You are the Soul of the trip: You aren't a tour guide reading from a script. You’re the person who sets the tone, breaks the ice, brings the group together and makes sure everyone feels included. - You’re the Fixer: When a flight is delayed or a plan changes, you don’t sweat it. You pivot and keep the energy high. Who we’re looking for This is for the natural-born leaders. The ones who are always "the planner" in their friend group. - Social Intelligence: You can read a room and handle group dynamics like a pro. - Resourcefulness: You’re grounded and practical. You find solutions while others are still looking for the problem. - Energy: You’re adventurous, empathetic, and genuinely love meeting new people. Who should apply We’d love to hear from you if you: - Are in your 20s, 30s - Love group experiences and human connection - Feel aligned with WeRoad’s vision and values The Perks - Travel the World: While you’re leading a trip, the experience is on us. We handle the flights, the stays, and the itinerary. You bring the energy; we provide the world. - The Global Community: Gain instant access to our worldwide community of thousands of leaders. - Master Leadership: This is a real-world masterclass in crisis management and people skills that you just can't get in a cubicle. How the selection process works We don’t do boring HR interviews. We want to see your energy in action. - The Application: Show us your vibe. We want to know you! - The Bootcamp (May 16-17): If your application stands out, we’re inviting you to Austin, Texas. The Austin Bootcamp* is a high-energy, 2-day selection event. It’s part connection, part challenge, and 100% WeRoad. Show us you can lead the pack, and you’re in. *Note: for the Austin Bootcamp, accommodation and other inclusions will be explained when relevant Ready to lead the world? Read the vision. Catch the vibe and apply!

• Champion the vision for digital products, inspiring teams to deliver innovative solutions that drive business growth and elevate customer experiences. • Lead cross-functional collaboration, uniting business and technology partners to turn strategic ideas into impactful, scalable digital capabilities. • Own the end-to-end product lifecycle, ensuring every initiative is executed with precision, clarity, and measurable results. • Empower teams by breaking down complex challenges into actionable roadmaps, fostering transparency and momentum across global projects. • Proactively identify opportunities, remove obstacles, and accelerate progress, ensuring every milestone delivers meaningful value. • Leverage data-driven insights to continuously optimize product performance, keeping the team focused on high-impact work and adapting to evolving needs. • Drive a culture of continuous improvement, championing new technologies and processes that keep Deckers Brands at the forefront of digital innovation.