21tech | Talent Table

Our client, a global technology and financial services company, is seeking a Field Sales Rep - City Launch & Merchant Success.

This is a 6-month contract position. Candidates must be located in or able to work in the Chicago, IL area and be authorized to work in the United States. Hourly rate: $63.86. No C2C.

About the Role:

You will help drive merchant adoption, education, and long-term engagement across launch markets. This is a field-based role where you'll spend the majority of your time meeting merchants face-to-face, supporting launches, leading trainings, gathering feedback, and building strong relationships within local business communities.

You Will

• Be the face of the program in your city, building trusted relationships with local merchants.
• Spend your days in the field visiting restaurants and other local businesses, helping them launch and succeed.
• Own the field launch lifecycle from pre-launch readiness through activation-day support and post-launch follow-up, including live transaction walkthroughs with owners, managers, and frontline staff.
• Explore opportunities to build a vibrant local merchant community through workshops, events, office hours, and other methods of ongoing engagement.
• Partner with Product, Operations, and Go-to-Market teams to execute successful city launches and market expansion.
• Gather merchant feedback, identify operational challenges, and advocate for improvements that make the program even better.
• Monitor merchant engagement and adoption, proactively helping businesses maximize their success.
• Roll up your sleeves to solve problems, remove obstacles, and deliver an exceptional merchant experience in partnership with merchants' Account Managers where applicable.
• Develop repeatable playbooks, training materials, and community engagement strategies that can scale to future cities.

You Have

• 5-7+ years of experience in merchant success, hospitality, field operations, community management, training, account management, retail, restaurant operations, or other customer-facing roles.
• You genuinely enjoy meeting new people and quickly building authentic relationships.
• You thrive in fast-paced, entrepreneurial environments where you're expected to take initiative, solve problems, and make things happen.
• You're comfortable walking into a local business, introducing yourself to owners and staff, and earning trust through genuine conversation.
• You have experience leading trainings, facilitating workshops, or educating customers in a way that's engaging and memorable.
• You're highly organized, dependable, and follow through on commitments.
• You balance strategic thinking with a willingness to jump in and do whatever it takes to help merchants succeed.
• You're excited to spend the majority of your time in the field, traveling locally (within approximately 100 miles of your assigned market) to visit merchants, lead trainings, and support community events.
• You're passionate about local businesses and believe strong communities are built by helping independent businesses thrive.