Head of Finance

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, Switzerland and… the USA!

With 200 team members and 4K 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 1000+ 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 through our Cultural Manifesto 👥

ABOUT THE ROLE

JOB TITLE: Head of Finance

LOCATION: Hybrid (Milan)

TYPE OF CONTRACT: Full-Time, Permanent

SALARY RANGE: €75,000 – €85,000 gross per year

What you'll do:

• Lead, coach and grow a Finance team of approximately 10 people across Accounting, Tax and Treasury, setting clear priorities, objectives and ways of working.

• Oversee the full accounting cycle, including monthly, quarterly and year-end closing, ensuring accurate, timely financial statements across all WeRoad entities.

• Supervise tax compliance and planning (direct and indirect taxes, including travel-specific VAT regimes), working closely with tax managers and external advisors.

• Manage treasury and cash flow, including liquidity planning, banking relationships, multi-currency payments and working capital optimisation.

• Partner with the FP&A on budgeting, planning and forecasting, providing reliable data and insights to support business decisions.

• Drive process improvement and automation across Finance, strengthening internal controls and scaling our systems as the company grows internationally.

• Act as a key point of contact for auditors, tax advisors and banks, and support reporting to the Board and investors.

What we're looking for:

• At least 5 years of experience in a senior finance management experience, ideally in a fast-growing, multi-entity and international environment..

• Solid background in accounting, tax and treasury, with a strong command of Italian GAAP; knowledge of IFRS is a plus.

• Proven experience in budgeting, planning and forecasting processes.

• Track record of leading and developing teams of around 10 people, with a hands-on, results-oriented leadership style.

• Strong analytical mindset, attention to detail and the ability to translate numbers into clear business insights.

• Familiarity with ERP systems (experience with Microsoft Business Central is a plus).

• Tech-savvy mindset with hands-on experience using automation and AI tools to streamline finance processes (e.g. reconciliations, reporting, forecasting), and the drive to lead the team in adopting them.

• Fluent English and Italian.

You will love working at WeRoad if:

• You dream big, aim higher, and push yourself beyond limits you didn't think possible. Challenges excite you, and you're hungry for the next win.

• You want to be part of a young, smart, and fun team that shares your passion for travel. You thrive in a community of bold thinkers and doers who challenge and inspire each other.

• You're an entrepreneur at heart, take responsibility from day one, and move fast to make things happen.

• You prefer adventure over routine and embrace the fast-paced, ever-changing ride of a scaleup. You make decisions quickly, test, learn, and adapt—because growth comes from action.

• You believe in the power of people. Our WeRoaders and Travel Coordinators are at the core of everything we do, and you're eager to be part of something bigger.

BENEFITS

• Performance-based bonus – A discretionary annual variable bonus, based on performance and company results.

• A free WeRoad trip every year – Choose your dream destination with €1,400/year travel discount or travel even more as a Travel Coordinator.

• Trust-based holidays – We believe performance is driven by impact, not by hours at a desk. You are encouraged to take the time you need to recharge, beyond contractual minimums, within shared guidelines.

• 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 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.

SELECTION PROCESS

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. With multiple steps, we make sure every new joiner is not just a match, but 150% aligned with our Culture.

The selection process will consist of:

• Introductory call with Talent Acquisition Lead

• Case Study

• Technical and background-based interview

• Bar Raiser step

WeRoad is an equal opportunity employer: we consider for employment all applicants, regardless of their race, religion, color, ancestry, national origin, sex, sexual orientation, gender, gender identity, age, family status, political affiliation, disability, and any other legally protected characteristic.

Statistically speaking, women are less likely to apply for roles where they don't fit the job description perfectly. Don't let a checklist hold you back: if you're passionate about the role we encourage you to apply with enthusiasm!