Head of Sales and Customer Experience

Overview

Head of Sales and Customer Experience role at WeRoad

ABOUT WEROAD: CONNECTING PEOPLE, CULTURES, AND STORIES

Founded in 2017, WeRoad is a fast-growing startup that is disrupting the travel industry in Italy, Spain, UK, Germany, France and Switzerland. With 200 team members and 3K Travel Coordinators, we’re a community of travelers who turn every trip into a life-changing experience. We connect like-minded millennials and send them on adventures to 300+ destinations worldwide. We’re on a mission to design and deliver experiences worth living and sharing, through rewriting the rules of the travel industry. Sounds exciting? Before you apply, please read throughour Cultural Manifesto

About the role

JOB TITLE: Head of Sales and Customer Experience
LOCATION: Milan (Hybrid)
TYPE OF CONTRACT: Permanent, Full Time
SALARY RANGE: up to €70K gross + bonus

What you’ll do

• Own the end-to-end Sales & Customer Experience strategy for our markets, from the very first user interaction to their entire journey. Design a coherent and holistic journey across every touchpoint (calls, WhatsApp, emails), with a strong coordination with the CRM team and Consumer Tech Ops
• Guide the team to deliver top-notch consumer assistance quality, always delivering the WOW factor and be able to reach high targets of sales conversion, SLAs and consumer satisfaction levels.
• Manage, motivate and develop the Sales & Customer Operations team, currently counting 15 FTEs.
• Pull team development and technology levers to balance the value of team interaction and AI/tech platform scalability and efficiency.
• Set up continuous sales and post-sales trainings to keep improving our team in supporting WeRoaders and offering the best caring initiatives in case of unmatched travel experience.
• Coordinate with CRM team to develop retention and engagement strategies for past WeRoaders by analyzing cohorts and tailoring lifecycle communications and win-back actions.
• Manage tour offering from a sales & customer experience lens: oversee attributes and status, coordinate new allocation requests and drive actions that maximize sales, fill rate and trip experience.
• Activate high-impact acquisition levers with Marketing & Community (e.g., referral, flash promos), bringing creativity to new sales plays while keeping the experience seamless.
• Maintain up-to-date knowledge of Consumer & CRM platforms and AI agentic solutions landscape .

What we’re looking for

• 4+ years’ experience in Sales & Customer Operations with team leadership; proven record scaling processes and consistently hitting targets/SLAs.
• Strong managerial skills to motivate and boost team performance— always providing a vision and a clear strategy on the “why.”
• Analytical to the core: you structure decisions on funnel metrics.
• Drive & ownership: energetic , resilient and excellence-obsessed—you persevere through adversity until the job is done impeccably.
• “Listen to listen,” not to answer, empathetic with both team and customers to surface unspoken needs and desires.
• Hands-on & sharp : lead by example, prioritize, close the loop, say “no” when needed;
• Fluent in Italian & English (German, French or Spanish is a plus).
• Out-of-the-box thinker with pragmatic speed: challenge “we’ve always done it this way,” learn fast, and find a way to make it happen.

What we can offer

• Performance-based bonus – A discretionary annual variable bonus, based on performance and company results.
• Stock options
• A free WeRoad trip every year – Choose your dream destination with €1,200/year travel discount or travel even more as a Travel Coordinator.
• Unlimited holiday – You are a master of your own time.
• Opportunities to learn – We invest in your growth with training and learning opportunities.
• New parent support – €3,600/year for 3 years after birth or adoption (or prorated if your child is under 3 when you start at WeRoad).
• Extra benefits – Meal vouchers (€8/day – when applicable), a €1,000 bonus for your wedding or civil union, and a one-off bonus when you hit 5 years with us.
• Fun – A vibrant co-working space, team buildings and meet-ups.
• Hybrid working – Flexible working, and we support you to work from your destination of choice up to 1 month per year.

Ready to apply?

At WeRoad, cultural fit matters as much as skills. We assess both the what—what someone brings—and the how—how they work and live our values. The selection process will consist of:

• Introductory call with People
• Technical and background-based interview with Hiring Manager (Regional Manager)
• COO Step
• Bar Raiser (our Founder Paolo) and CMO

WeRoad is an equal opportunity employer: we consider for employment all applicants, regardless of race, religion, color, ancestry, national origin, sex, sexual orientation, gender, gender identity, age, family status, political affiliation, disability, or any other legally protected characteristic. Don’t let a checklist hold you back: if you’re passionate about the role we encourage you to apply with enthusiasm!

EEO Statement WeRoad is an equal opportunity employer and values diversity in its workforce.