Sales Trainer - Inside Sales & Account Management (Fixed term)

SumUp; Milan (MI); On-site; USD 44,000 - 58,000; Full time

Benefits offered by this job

Global team collaboration

Stock option programme

Annual L&D budget €2000

22 days annual paid leave

Ex Festivita 32 hours

Corporate pension contributions

Mental health support

Job summary

SumUp in Milan, Italy seeks an experienced Sales Training Manager to design and deliver live onboarding and ongoing skills development for telesales and account management teams across Europe.

You'll build programmes that improve product knowledge, sales techniques, and multi-product selling, partnering with EU teams to tailor content for local markets. Travel to Europe is expected on a regular cadence.

Qualifications

• Experience delivering sales training in a live setting, including facilitation and active coaching.
• Ability to design and adapt training materials for multiple markets and languages.
• Strong knowledge of value selling and coaching techniques for sales reps.

Responsibilities

• Design and deliver live training sessions for Telesales and Account Management reps.
• Run onboarding sessions introducing SumUp's products and core skills.
• Track training impact through assessments and shadowing; adjust sessions accordingly.
• Support new hires and Team Leads with structured follow ups as they ramp up.
• Partner with EU Training Leadership to build programmes improving sales volume and multi-product selling.
• Share best practices with the wider Sales Enablement team across Europe.

Skills

Sales training

Live facilitation

Coaching

Multilingual

Travel availability

Job description

Location: Milan, Italy (office first) Contract type: Fixed term, full time

The team

Sales Enablement sits at the heart of how SumUp's Telesales and Account Management teams grow, turning product launches and market shifts into training that reps can use from day one. As we expand our merchant base into new markets and win larger, more complex accounts, the team's job is to make sure every rep can sell with confidence and credibility. This role owns onboarding and skills development for reps across two European markets, giving newly hired talent the tools to hit the ground running and existing reps the coaching they need to grow.

What you'll do

• Design and deliver live training sessions for Telesales and Account Management reps, covering both product knowledge and sales skills
• Run new joiner onboarding sessions that introduce SumUp's products and the core skills each role needs
• Track the impact of training through assessments and shadowing, adjusting sessions based on what's working
• Support new hires and their Team Leads with structured follow ups as they ramp up their sales performance
• Partner with Team Leads and the EU Training Leadership to build programmes that improve sales volume, quality, and multi product selling
• Share best practices with the wider Sales Enablement team across Europe

You'll be great for this role if…

• Experience delivering sales training in a live setting, including facilitation and active coaching
• A background in Telesales or account management, ideally within a fast paced, high volume sales environment
• Strong knowledge of value selling techniques and how to turn product knowledge into practical training
• Ability to build and adapt training materials, including role play scenarios and assessments
• Comfort working across multiple markets and languages, adapting content and delivery to local needs
• Availability to travel within Europe, approximately every other month

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 can be used to attend conferences and/or advance 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

Salary range: €39,040 to €52,053

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.