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

Sumup; Milano; On-site; EUR 39,000 - 52,000; Full time

Benefits offered by this job

Annual L&D budget of €2000

22 days annual leave + 32 hours ExFest

Pension contributions

Mental health support (EAP)

Break4me sabbatical after 3 years

Referral bonus

Job summary

SumUp in Milan is seeking a Sales Enablement Trainer to design and deliver live onboarding and ongoing skills development for Telesales and Account Management across Europe.

You will run onboarding, coach reps, and track impact, adapting content for local markets. The role requires travel within Europe, approximately every other month, and a passion for practical, results‑oriented training.

Qualifications

• Experience delivering sales training in a live setting, including facilitation and active coaching.
• Background in Telesales or account management within a fast paced, high volume sales environment.
• Strong knowledge of value selling techniques and how to turn product knowledge into 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.

Responsibilities

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

Skills

Live training delivery

Telesales experience

Account management experience

Value selling knowledge

Training materials creation

Multilingual communication

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.