Field Sales Training Team Lead

About SumUp

We believe in the everyday hero. Those who have the courage to follow their passion and who have the strength and determination to realise their dreams.

Small business owners are at the heart of all we do, so we're creating powerful, easy-to-use financial solutions to help them run their businesses. With a founder’s mentality and a team-first attitude, our diverse teams across Europe, South America and the United States work together to ensure that small business owners can be successful doing what they love.

Team Description

You’ll join the Sales Training team, sitting within our Sales Enablement function. Based in our hubs across Europe, they are focused on helping our Field Sales teams succeed quickly, confidently, and consistently.

As Sales Training Team Lead, you’ll be the operational and people lead for Field Sales Training in established markets. You’ll coach and support a team of experienced Field Sales Trainers, ensuring training is delivered on time, to a high standard, and with clear impact on field performance.

You’ll sit at the centre of execution, turning strategy into action and bringing clarity to day-to-day delivery. Working closely with Field Sales leadership, RevOps, and Product, you’ll keep training tightly connected to what’s happening in the field — from onboarding and accreditation through to early activation, productivity and ongoing training.

👉 Get a feel for our Milan office here

What You’ll Do

• Lead and support a team of Field Sales Trainers, setting clear priorities and ensuring high-quality delivery across markets

• Own the execution of onboarding, accreditation, and ongoing field sales training, maintaining consistency and standards

• Coach and develop trainers through observation, structured feedback, and regular performance conversations

• Monitor onboarding effectiveness and outcomes, adjusting training focus when results are off track

• Act as the link between the EU Sales Training Manager and the trainer team, translating priorities into clear actions

• Partner with Field Sales leadership, RevOps, and Product to ensure training is timely, relevant, and performance-driven

You’ll Be Great for This Role If

• You bring 3–5 years of sales training experience, with a strong understanding of onboarding and early performance drivers

• You have 1–3 years of people leadership or coaching experience

• You have solid sales knowledge from live selling environments

• You’re comfortable owning operations across remote teams or markets and using data to guide decisions

• You communicate clearly, collaborate well, and take ownership of outcomes

Nice to have:

• Fluency in French, German, Spanish, or Italian

• Experience in fintech, payments, or POS

• Exposure to Product or RevOps collaboration

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 VSOP program: you will own a stake in SumUp’s future success

📚 Invest in your growth: €2,000 annual Learning & Development budget to fuel your development

🏖 Generous time off: enjoy 22 days of annual paid leave, 32 hours of Ex Festività (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

At SumUp, we’re on a mission to empower small businesses around the world with simple, affordable tools to help them start, run, and grow. More than 4 million merchants across 36 markets trust us as their financial partner — and we’re just getting started.

We’re a global team of 3,000+ people from over 90 nationalities, united by curiosity, collaboration, and care. Our core values and culture shape everything we do, fostering inclusion, learning, and belonging.

SumUp is proud to be an Equal Employment Opportunity employer, committed to building a safe, respectful, and diverse workplace where everyone can thrive.

👉 Explore more about our culture on our careers site, or follow us on LinkedIn and Instagram.