Outside Sales Senior Account Executive - Chicago, IL

SumUp • Illinois, United States, IL

20h • Onsite

About The Position

SumUp’s Field Sales team expands into new markets and builds relationships with small and medium-sized businesses. The Outside Sales Senior Account Executive owns an assigned territory, manages the full sales cycle, and serves as a trusted local representative of SumUp. With support from a Team Lead and Regional Manager, the role has autonomy to build a sales pipeline, close new business, and grow earnings. The position is field-based and territory-driven, involving in-person visits to local businesses.

Requirements

• Prior sales experience in fintech, payment processing, or point-of-sale (POS) solutions is required.
• Comfort working independently in a field-based, territory-driven sales environment.
• Ability to connect with people, ask relevant questions, listen carefully, and adapt communication to each merchant.
• Comfort with cold outreach and face-to-face prospecting, including visiting local businesses.
• Valid driver’s license and reliable transportation to travel throughout the assigned territory.
• Self-motivated, resilient, and results-driven, with an ambition to develop skills, career, and earning potential.

Responsibilities

• Build and manage a strong sales pipeline in the assigned territory through prospecting, canvassing, referrals, and relationships with local businesses.
• Manage the full sales cycle, from cold outreach and door-to-door prospecting through discovery, product demonstrations, negotiation, and closing.
• Build merchant relationships by understanding each business’s needs and recommending appropriate SumUp solutions.
• Research the territory, identify high-potential opportunities, and prioritize time effectively.
• Use Salesforce to track activity, manage opportunities, and maintain consistent follow-up.
• Represent SumUp’s payment and loyalty solutions to local merchants and explain how they can support their businesses.

Benefits

• $2,000 annual learning and development budget.
• 22 days of paid vacation, 8 sick days, public holidays, quarterly wellness days, and additional special leave.
• Medical, dental, and vision coverage through Cigna and Kaiser.
• Life insurance and disability coverage.
• 401(k) retirement plan with SumUp matching.
• Uncapped commission and earning potential.
• Opportunities for career advancement and increased compensation tied to performance and impact.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed