Outside Sales Account Executive - Chicago, IL

Outside Sales Account Executive - Chicago, IL

Outside Sales | Account Executive SumUp

Location: Chicago, IL

This is a field sales role

Employment type: Full-time, permanent

Start Date is October 15th, 2026

About the team

SumUp's field sales team is on the ground, expanding across the country building real relationships with the small businesses that make up the heartbeat of local communities across the US. This team doesn't sell from behind a desk they're out in the field, helping merchants discover tools that genuinely change how they run their businesses. As a Field Sales Representative, you'll own your territory, manage a full sales cycle, and be the face of SumUp for the merchants you serve. If you're driven by results, care about the people you work with, and want uncapped earning potential with a clear path to grow, this is the role for you.

What you'll do

• Build and manage a territory-based sales pipeline by prospecting, canvassing, and developing relationships with local businesses
• Run the full sales cycle from cold outreach and door-to-door canvassing through to close
• Research your territory to work smarter, identify the right opportunities, and prioritize your time effectively
• Use our CRM to track activity, manage your pipeline, and keep communication sharp
• Represent SumUp's payment and loyalty solutions in a way that genuinely helps merchants grow

You'll be great for this role if

• Experience in sales, whether in retail, hospitality, B2B, or SaaS we care more about your drive than your exact background
• Comfort working independently in a field-based, territory-driven environment
• Strong ability to connect with people quickly, listen well, and tailor your approach to each customer's needs
• Reliable access to transportation to cover your assigned territory
• A track record of being self-motivated, resilient, and hungry to grow even if you're still early in your career

Why you should join SumUp

Opportunity to work with SumUppers globally on large-scale fintech products used by millions of businesses worldwide, in a remote-first field role across the US

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

Generous time off: 22 days of paid vacation, plus an extra day each year up to 28 days, public holidays, quarterly Wellness Days, and special leaves

Health and life coverage: medical coverage via Cigna, plus life insurance

Financial security: 401(k) retirement scheme with SumUp matching

Break4me: 1-month sabbatical after 3 years of service

Referral Bonus: earn additional rewards by referring talented individuals to join the SumUp team

Compensation

On-target earnings of USD 107,000 with uncapped commission ($50,000 base salary) the harder you work, the more you earn

Clear opportunities for advancement and increased compensation based on performance

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 37 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 3,000 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, color, 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.

Job Application Tip

We recognize 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.