Sales Development Representative
EU GTM | Milan, Italy
About the team 🙌SumUp is one of the fastest-growing fintechs in Europe — and our SDR team in Milan is a big part of that story. You'll be the first voice small business owners in Italy hear from SumUp, opening doors and sparking real conversations that turn into pipeline. No scripts, no micromanagement. Just a driven team, clear targets, and a real path to build a sales career at a global fintech. If you're hungry, coachable, and love a good conversation — keep reading. 👇
What you'll do📞 Reach out to small business owners across Italy via calls, emails, and other channels to book qualified appointments
🎯 Qualify leads by getting curious about each prospect's business — and figuring out if SumUp is the right fit
🤝 Hand off opportunities to field sales reps with clean, well-documented notes so nothing gets lost
📊 Keep your CRM up to date — activity, pipeline, and progress, always accurate
🏆 Hit (and beat) your weekly and monthly targets for outbound activity and appointments set
💬 Share what's working with your team — good ideas spread fast here
📈 Level up constantly through coaching sessions, call reviews, and team learning
You're confident and energetic — you enjoy talking to strangers and making them glad you called
You're target-driven and take full ownership of your performance
You're organised and consistent — you know the daily grind is what builds the pipeline
You're coachable, open to feedback, and always looking to get better
You're comfortable in a fast-paced environment where things move quickly and no two days look the same
You speak Italian natively and have a working level of English for internal comms
💸 Competitive base salary + uncapped commission — your earning potential grows with your success!
🌎 Work with global impact — Join a fintech used by over 4 million businesses in 37 markets, from our Milan office
🌈 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
📚 A dedicated annual L&D budget for attending conferences and/or advancing your career through further education
🏖 22 days paid leave plus public holidays and Personal Hours (starting at 32h/year, increasing after 2 and 4 years of service)
🥗 Restaurant ticket — subsidised meals every day
🚇 Public transport ticket (50% subsidised)
📱 Phone allowance — for sales team members
🗣️ Free Babbel Professional Subscription — keep growing your language skills
🏅 Convenzioni Aziendali — exclusive corporate discounts
💰 Pension Plan — investing in your future
🔗 Referral Program — earn rewards for bringing great people in
🌴 Break4me — 1-month sabbatical after 3 years of service
About SumUpBe 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. 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. Discover more about our culture and opportunities on our careers website, and follow our journey on LinkedIn, Instagram, and TikTok.
Keywords: Sales Development Representative, SDR, Outbound Sales, Inside Sales, Sales Representative, Sales Executive, Business Development, Lead Generation, Telesales, Account Executive, Sales Consultant, Sviluppo Commerciale, Commerciale, Telemarketing, Vendite, Rappresentante Commerciale, B2B Sales, Fintech Sales, Milano, Milan
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.
Skills Required
- Native Italian speaker with good English skills.
- Experience in, or strong interest in, outbound sales and cold calling.
- Enjoy speaking with people and building trust quickly.
- Thrive in a fast-paced, target-driven environment.
- Desire to build a long-term career in sales and technology.
SumUp Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about SumUp and has not been reviewed or approved by SumUp.
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Leave & Time Off Breadth — Paid time off is positioned as a standout, including 22 vacation days that increase with tenure, public holidays, a quarterly Wellness Day, special leave, and a fully paid one‑month sabbatical after three years. This combination makes time-off benefits feel notably robust in the overall rewards package.
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Healthcare Strength — Health coverage is described as comprehensive, with medical plan options (including carriers such as Cigna and Kaiser) plus dental and vision. Company-paid life insurance and disability coverage are also part of the protection package in the U.S. materials.
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Retirement Support — Retirement benefits include a published 401(k) match formula that provides an employer match up to a stated cap. The clarity of the match structure supports straightforward evaluation during offer comparisons.
SumUp Insights
What We Do
SumUp believes that every business should have access to affordable, easy-to-use financial solutions, no matter their size. That’s why more than 3 million businesses worldwide rely on SumUp to run their business. What started out as one card reader has now turned into a range of payment hardware, banking solutions, marketing, and loyalty tools, invoicing, and so much more. From sales and marketing to product and engineering, our cross-functional US team works together to ensure that small business owners can be successful doing what they love.
Why Work With Us
SumUp USA is part of the global SumUp organization that stretches across multiple continents from Berlin to Sao Paulo. Our teams are multicultural, have a collaborative mindset and bold goals. Join our mission if you want to become part of the success story and help empower over 3 million merchants using SumUp already!
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