Milan, Italy (office first) Contract type: Fixed term, tempo pieno
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.
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
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
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 emb

📌 Sales Trainer (Italia)
🏢 Sumup
📍 Italia