Outside Sales Account Executive - Chicago, IL

Socket.dev; Chicago (IL); On-site; USD 100,000 - 114,000; Full time

Benefits offered by this job

Learning & development budget $2,000

Paid vacation 22 days

Sick days 8 days

Health insurance

401(k) with matching

Uncapped earning potential

Career growth opportunities

Job summary

SumUp is seeking an Outside Sales Account Executive to own a local Chicago territory, drive the full sales cycle, and build lasting merchant relationships. This field-based role offers uncapped earning potential and a clear path for career growth.

You’ll prospect, demonstrate SumUp solutions, negotiate, and close deals with local businesses while using Salesforce to manage a thriving pipeline and exceed targets. A self-motivated, customer-focused professional will thrive in this role.

Qualifications

• Field sales experience or B2B sales background preferred.
• Ability to travel within the assigned territory and manage in-person meetings.
• Strong prospecting, discovery, negotiation, and closing skills.
• Customer-centric approach with the ability to tailor solutions to merchants.
• Reliable transportation and self-motivation to meet targets.

Responsibilities

• Own your territory and build a robust sales pipeline through prospecting and local outreach.
• Lead the full sales cycle from discovery to close, including product demonstrations and negotiations.
• Develop merchant relationships by understanding needs and recommending SumUp solutions.
• Research territory to identify high-potential opportunities and prioritize time effectively.
• Maintain pipeline in Salesforce and provide timely follow-up with prospects.
• Represent SumUp as a local ambassador to help merchants grow their businesses.

Skills

Sales experience

Prospecting

Negotiation

Customer relationships

Territory management

Communication

Job description

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

About the team

SumUp’s Field Sales team is on the ground, expanding into new markets across the country and building real relationships with the small and medium-sized businesses that power local communities.

Every day, our team meets merchants face-to-face, helping them discover payment and loyalty solutions that can make running and growing their businesses easier.

As an Outside Sales Account Executive, you’ll take ownership of your territory, manage the full sales cycle, and become a trusted face of SumUp for the merchants you serve. With the support of your Team Lead and Regional Manager, you’ll have the autonomy to build your pipeline, close new business, and grow your earnings.

If you’re motivated by results, enjoy connecting with people, and want uncapped earning potential with a clear path for career growth, we’d love to hear from you.

What you'll do

• Own your territory by building and managing a strong sales pipeline 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 close.
• Build meaningful merchant relationships by understanding each business, identifying its needs, and recommending the right SumUp solutions.
• Work strategically by researching your territory, identifying high-potential opportunities, and prioritizing your time effectively.
• Stay on top of your pipeline using Salesforce to track activity, manage opportunities, and maintain clear and consistent follow-up.
• Be a local ambassador for SumUp by confidently representing our payment and loyalty solutions and showing merchants how SumUp can help their businesses thrive.

You'll be great if the following describes you…

• Have sales or customer-facing experience in retail, hospitality, B2B, SaaS, or a similar environment. We care more about your drive and potential than a specific number of years in sales.
• Are comfortable working independently in a field-based, territory-driven sales environment.
• Can connect with people quickly, ask the right questions, listen carefully, and adapt your approach to each merchant.
• Are comfortable with cold outreach and face-to-face prospecting, including visiting local businesses within your territory.
• Have reliable access to transportation to travel throughout your assigned territory.
• Are self-motivated, resilient, and results-driven, with the ambition to grow your skills, your career, and your earning potential.

Why you should join SumUp

Make an impact at a global fintech Collaborate with SumUppers around the world on large scale fintech products that help millions of businesses succeed.

US based Customer Experience team in Texas that can support both English and Spanish speaking merchants

Invest in your growth Receive a $2,000 annual learning and development budget to build new skills and support your career development.

Take time to recharge Enjoy 22 days of paid vacation, 8 sick days, public holidays, quarterly wellness days, and additional special leave.

Comprehensive health and protection benefits Access medical, dental, and vision coverage through Cigna and Kaiser, along with life insurance and disability coverage.

Build your financial future Participate in our 401(k) retirement plan with SumUp matching

Compensation

Uncapped earning potential Earn $107,000 in on target earnings (OTE), including a $50,000 base salary, with uncapped commission and no ceiling on your earning potential.

Grow your career and your earnings Take advantage of clear opportunities for career advancement and increased compensation, with growth directly tied to your performance and impact.

About SumUp

Be empowered to do more that matters.

At SumUp, we're on a mission to empower merchantsacross the globe by providing simple and affordable tools that allow them to thrive. Today, over 4 million businesses in 38 countries 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 4,000 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, colour, 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, and follow our journey on LinkedIn, Instagram, and TikTok.

#SumUpUSA