Outside Sales Senior Account Executive — Chicago

Job overview

The Outside Sales Senior Account Executive role is field-based in Chicago, IL, serving an assigned territory. Compensation is $129,800 in on-target earnings, including a $65,000 base salary, plus uncapped commission. SumUp’s Field Sales team builds relationships with small and medium-sized businesses and offers payment and loyalty solutions. The account executive owns the territory and manages the full sales cycle, from prospecting and discovery through demonstrations, negotiation, and closing. The role helps merchants identify suitable solutions while growing SumUp’s local customer base and sales pipeline.

What you'll do

• Build and manage a territory pipeline through prospecting, canvassing, referrals, and local business relationships
• manage the sales cycle from outreach through close
• understand merchant needs and recommend solutions
• research and prioritize territory opportunities
• track activity and follow-up in Salesforce
• represent SumUp’s payment and loyalty solutions.

What we're looking for

Skills & competencies

outside sales

senior account executive

fintech

payment processing

point of sale

territory sales

small business

chicago il

sumup

$65k base

$129.8k ote

uncapped commission

Work arrangement

• Weekend coverage required

Benefits & perks

• $2,000 annual learning and development budget
• 22 days paid vacation
• 8 sick days
• public holidays
• quarterly wellness days
• medical, dental, vision, life, and disability coverage
• 401(k) with company match

Why this role

Prior sales experience in fintech, payment processing, or point-of-sale solutions is required; valid driver’s license and reliable transportation are required for territory travel.

About the employer

SumUp is hiring for this role. Industry: International, Secondary Market, and All Other Nondepository Credit Intermediation. Sector: 52.