Head of Direct Sales Excellence Greater Milan, Italy Area

Head of Sales Excellence, Direct Sales

Team description

Direct Sales at SumUp spans Telesales and Key Accounts teams across multiple European markets, each led locally rather than by one central head, so you'll be the driver of keeping priorities, performance and ways of working aligned across the whole channel. You'll step into a pivotal year: Key Accounts is being scaled up, Telesales is shifting further into outbound selling, and new AI tools are being tested to help reps work smarter. This is a 12 month assignment covering parental leave, giving you full ownership of a senior, cross market leadership role with real initiatives to drive and a team to lead, not just a holding position.

What you'll do:

Build one clear view of how Telesales and Key Accounts are performing, spotting issues and improvement opportunities early

Run the channel's quarterly goal setting and keep initiatives on track, flagging risks and decisions before they become blockers

Lead change across the channel, from readiness and communication to checking that new ways of working actually stick

Turn feedback from sales teams into a prioritised list of fixes and improvements, working closely with the Enablement team

Coordinate initiatives across Pricing, Commercial Planning, Analytics and other partner teams so every workstream has what it needs to launch

Lead and develop a small team of sales excellence specialists, taking on the most complex initiatives personally

What you'll bring:

Significant experience leading sales operations, commercial operations, revenue operations or a similar function at a senior level, ideally including people leadership

Proven track record of partnering with senior Sales leaders to shape channel strategy and turn business priorities into clear, actionable goals

Strong skills in commercial performance analysis, able to read funnel, revenue and productivity data and translate it into practical recommendations

Confidence influencing senior stakeholders across Sales, Product, Marketing and Finance without relying on direct authority

Comfort working through ambiguity while leading complex, cross functional programmes from strategy through to execution

Nice to have: fluency in French, German, Spanish or Italian.

Why you should join SumUp

🌎 Opportunity to work with a truly global, multicultural team from our central Milam location, wrapped in historic charm and modern flair. 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 for attending conferences and/or advancing your career through further education

🏥 Health matters: private health insurance, including optical and dental

🛡 Peace of mind: life insurance from MetLife for 2× your salary

🌴 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 39 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 4,000 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.

Job Application Tip

We recognise that candidates feel they need to meet 100% of the job criteria in order to apply for a job. Please note that this is only a guide. If you don’t tick every box, it’s ok too because it means you have room to learn and develop your career at SumUp.