# Outside Sales Senior Account Executive - Chicago, IL at SumUp

SumUp is hiring an Outside Sales Senior Account Executive - Chicago, IL. It pays $130k a year and Level rates it Little AI ●○○○; you can [apply on Level](https://jobsbylevel.com/go/9b6f8574-9c65-494b-b8bd-2630b693bef3?utm_medium=ai-agent).

AI Level 1, AI centrality 36 out of 100. Illinois, United States.

## Details

- Company: [SumUp](https://jobsbylevel.com/companies/sumup)
- AI level: AI Level 1 (score 36 out of 100)
- Location: Illinois, United States
- Salary: $130k
- Posted: October 19, 2026
- Apply: https://jobsbylevel.com/go/9b6f8574-9c65-494b-b8bd-2630b693bef3?utm_medium=ai-agent

## Description

Outside Sales Senior Account Executive Location: Chicago, IL 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 Senior 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… Candidates must have prior sales experience in fintech, payment processing, or point-of-sale (POS) solutions . This is a required qualification , not a preferred one. 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 a valid driver’s license and reliable 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 $129,800 in on target earnings (OTE), including a $65,000 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 merchants across the globe by providing simple and affordable tools that allow them to thrive. Today, over 4 million

The description is cut here. Read the full offer: https://jobsbylevel.com/jobs/outside-sales-senior-account-executive-chicago-il-at-sumup-13c214

Source: https://jobsbylevel.com/jobs/outside-sales-senior-account-executive-chicago-il-at-sumup-13c214

## Cite this page

Level. https://jobsbylevel.com/jobs/outside-sales-senior-account-executive-chicago-il-at-sumup-13c214.

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