Field Sales Rep – City Launch & Merchant Success

Location: Onsite — New York, Los Angeles, San Francisco Bay Area, Seattle, Portland, Chicago, Austin, San Diego, Philadelphia, or Atlanta (NY & LA High Priority). Duration: 6 months.

About the Company

The Company is building tools that help local businesses thrive. Neighborhoods is a local rewards network that connects both sides of the ecosystem, helping Cash App customers and independent businesses on Square, giving them new ways to attract customers, build loyalty, and drive repeat visits. By connecting local businesses through shared customer experiences, Neighborhoods helps strengthen local commerce and neighborhood economies.

We’re looking for people who love being out in the community, making new connections, and helping local businesses succeed. If you’re the kind of person who gets energy from walking into a restaurant, introducing yourself to an owner, solving problems on the spot, and turning first conversations into lasting relationships, this role is for you. Neighborhoods is an early-stage initiative, so we’re looking for entrepreneurial operators who enjoy building from the ground up. You’ll spend most of your time in the field helping merchants launch successfully, leading trainings, gathering feedback, and building a vibrant community of local businesses. Every day is different, and your work will directly influence how Neighborhoods grows.

About the Role

The company is seeking a City Launcher, Merchant Success & Community to drive merchant adoption, education, and long-term engagement for Neighborhoods across launch markets. This is a 6-month contract, field-based role where you’ll spend the majority of your time meeting merchants face-to-face. Travel is primarily local (within approximately 100 miles of your assigned market) and includes frequent visits to businesses, community events, and merchant training.

You’ll be the face of Neighborhoods in your city—building relationships with local business owners, leading engaging onboarding and training sessions, hosting community events, and ensuring merchants get lasting value from the program. You’ll also serve as the voice of the merchant, bringing insights from the field back to Product, Operations, and Go-to-Market teams to help shape the future of Neighborhoods.

Success in this role will be measured by merchant adoption, engagement, program retention, training effectiveness, community participation, and the quality of insights that help improve and scale the program.

Responsibilities

• Be the face of Neighborhoods 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.

Requirements

• 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.

Benefits

Individual compensation is determined by skills, qualifications, experience, and location. Full-time roles are eligible for Medical, Dental, Vision, Commuter and 401K benefits with company matching.