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SumUp

Outside Sales Account Executive - Chicago, IL

SumUp · Chicago, Illinois, United States

Posted 29 days ago

or apply directly on SumUp's site. We never take the application ourselves.

Is this posting real?

This role has been open
29 days
SumUp's roles stay open a median of 45 days
Reposted
No
Salary listed
No
1% of SumUp's roles list one
Ghost-job risk at SumUp
low
0 stale, 22 reposted of 409 open
Hiring momentum
564 roles opened in the last 90 days
↑ up vs. the prior 90 days
Last confirmed on the employer's board
2026-09-17

Measured from postings appearing on and disappearing from SumUp's own greenhouse board since 2026-08-03. Full hiring picture for SumUp.

About this role

As an Outside Sales Account Executive at SumUp, you will be responsible for managing a sales territory, building relationships with small and medium-sized businesses, and guiding them to discover payment and loyalty solutions. Your daily activities will include prospecting, conducting product demonstrations, and managing the full sales cycle from outreach to closing deals. You will work independently in the field and utilize Salesforce to track your sales activities and opportunities.

Our read on this posting3.4out of 5
benefits
4/5
freshness
4/5
career value
4/5
role clarity
5/5
pay transparency
0/5

Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of SumUp as an employer.

What you need

  • Sales or customer-facing experience in retail, hospitality, B2B, SaaS, or a similar environment
  • Comfortable working independently in a field-based, territory-driven sales environment
  • Ability to connect with people quickly and adapt your approach to each merchant
  • Comfortable with cold outreach and face-to-face prospecting
  • Reliable access to transportation to travel throughout your assigned territory
  • Self-motivated, resilient, and results-driven

What you get

  • $2,000 annual learning and development budget
  • 22 days of paid vacation
  • 8 sick days
  • Public holidays
  • Quarterly wellness days
  • Comprehensive health and protection benefits including medical, dental, and vision coverage

Worth weighing

  • Start date is in the future (October 15th, 2026)
  • Uncapped earning potential with a base salary and commission structure
  • Sales cycle includes cold outreach and door-to-door prospecting which may not suit everyone

Summarised from SumUp's posting. Read the full original.

Listed by SumUp on their greenhouse job board, last confirmed open on 2026-09-17. PitchMeAI is not the employer.

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