Department: Field Sales

Head of Regional Field Sales – Northern Italy | Sales

Milan

Team description

SumUp's Italian Field Sales team is one of the most ambitious in our European network — and Northern Italy is at the centre of that growth story. With a regional structure spanning Regional Managers, Territory Managers, and over 150 active consultants and internal full time Sales Executives, this is a large, complex, and high-potential operation. We're looking for a senior sales leader to take full ownership of the Northern region: driving performance, scaling the team, and embedding a culture of excellence across a distributed field force. This is a seat at the table of SumUp's Italian and European leadership, with real influence over how we grow in one of our most important markets.

What you'll do

• Lead and develop Regional Managers across Northern Italy, setting the performance standards, coaching rhythms, and team culture that underpin sustainable growth
• Own the commercial performance of the Northern region, driving multi-product revenue, managing profitability, and ensuring sales execution is aligned to the business plan
• Define and implement regional sales strategies, including territory planning, hub-level tactics, and structured performance management across the full field sales hierarchy
• Recruit, develop, and retain top Regional and Territory Manager talent, while supporting the broader consultant pipeline in a self-employed model
• Act as a key voice in the Italian and European leadership panel, contributing to wider field sales strategy, communication plans, and cross-functional initiatives
• Spend meaningful time in the field — coaching alongside your team, visiting merchants, and leading by example on the ground

What we’re looking for

• Extensive experience leading field sales teams at a senior level, with a track record of managing managers and scaling distributed sales operations.
• Deep knowledge of the merchant services or POS payments landscape in Italy, with a strong existing network and market intuition.
• Proven ability to build high-performance cultures within self-employed or freelance sales models, keeping teams motivated, engaged, and commercially focused.
• Strong analytical and commercial acumen, with experience using data to drive decisions on territory investment, performance management, and sales strategy.
• Fluency in Italian and English, with the executive presence and communication skills to operate confidently across leadership teams and in the field.

Why you should join SumUp

🌎 Opportunity to work with a truly global, multicultural team from our inspiring Milan location. This involves an office-first setup.
🌈 Commitment to Diversity and Inclusion: be part of a workplace that values and promotes diversity, fostering an inclusive environment where everyone's perspectives are respected and embraced.
🚀 Enrolment onto our Virtual Stock Option programme: you will own a stake in SumUp's future success.
📚 A dedicated annual L&D budget of €2000 for your individual development, which you can use to attend conferences and/or advancing your career through further education.
🏖 Generous time off: enjoy 22 days of annual paid leave, 32 hours of Ex Festivita (Personal Hours), plus public holidays and special leave days.
💼 Financial security: corporate pension contributions that support your long-term future.
❤ Well-being support: access our mental health Employee Assistance Programme for guidance and care when you need it.
🌴 Break4me: 1-month sabbatical after 3 years of service.
🔗 Referral Bonus: earn additional rewards by referring talented individuals to join the SumUp team.

About SumUp

Be empowered to do more that matters.

At SumUp, we're on a mission to empower small businesses across the globe by providing simple and affordable tools that allow them to thrive. Today, over 4 million businesses in 37 markets rely on SumUp as their financial partner to manage payments, finance and customer relationships.

Our commitment to small businesses is reflected in our diverse team of over 3,000 SumUppers from over 90 nationalities, united by global collaboration and an innovative mindset. Our core values lay the foundation for who we are and what we stand for, shaping our work culture and driving our success. We foster inclusivity and a continuous learning culture, providing a safe space for personal and professional growth. Our differences make us unique and strong as we strive to create an environment where everyone belongs and feels supported, no matter how they identify.

SumUp is proud to be an Equal Employment Opportunity employer, actively seeking and embracing diversity in our workforce. We don't make hiring or employment decisions based on race, colour, religion or religious belief, ethnic or national origin, nationality, sex, gender, gender identity, sexual orientation, disability, age or any other basis protected by applicable laws or prohibited by company policy. Our commitment extends beyond recruitment to creating a safe and respectful workplace where harassment of any form is strictly prohibited. Discover more about our culture and opportunities on our careers website, and follow our journey on LinkedIn, Instagram, and TikTok.