Field Sales Representative

The Planet Group; New York (NY); On-site; USD 34,000 - 55,000; Full time

Job summary

The Planet Group is seeking a field-based Merchant Success Specialist to engage local merchants, lead onboarding and training, and host community events within your assigned market. This 6-month contract focuses on building relationships and delivering lasting value.

You will travel locally, spend substantial time in the field meeting merchants, and collaborate with Product, Operations, and GTM teams to improve the program. Strong communication and organizational skills are essential.

Qualifications

• 5–7+ years in merchant success, hospitality, field ops or customer-facing roles.
• Proven ability to build authentic relationships quickly with local business owners.
• Experience leading trainings, workshops, or customer education programs.

Responsibilities

• Build trusted relationships with local merchants and staff.
• Serve as primary field representative for the assigned market.
• Spend the majority of time in the field visiting restaurants and local businesses.
• Manage the merchant launch lifecycle from pre-launch to post-launch.
• Conduct onboarding sessions, product demos and training.
• Develop workshops and community events to engage merchants.
• Monitor adoption, engagement, and retention; identify improvement opportunities.
• Collaborate with Product, Operations, GTM, and Account Management teams.
• Collect merchant feedback and report field insights to internal teams.
• Troubleshoot issues and provide hands-on support for a great merchant experience.
• Create scalable training materials and playbooks for future markets.
• Track launch progress, engagement, and training effectiveness.

Skills

Relationship building

Communication

Training delivery

Field operations

Time management

Presentation

Job description

Work Schedule: 4 days field work from Mon-Thu. Fri reserved for administrative/desk work. Equipment: MacBook

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.

Key Responsibilities:

• Build trusted relationships with local merchants, business owners, managers, and frontline staff.
• Serve as the primary field representative for Neighbourhoods within the assigned market.
• Spend the majority of time in the field visiting restaurants and other local businesses.
• Manage the merchant launch lifecycle from pre-launch preparation through activation, live transaction support, and post-launch follow-up.
• Conduct onboarding sessions, product demonstrations, transaction walkthroughs, and merchant training.
• Develop and facilitate workshops, office hours, community events, and other engagement activities.
• Monitor merchant adoption, engagement, and retention and proactively identify opportunities to improve participation.
• Partner with Product, Operations, Go-to-Market, and Account Management teams to support successful market launches.
• Gather merchant feedback and identify operational challenges, trends, and opportunities for improvement.
• Advocate for merchant needs and communicate field insights to internal teams.
• Troubleshoot issues, remove obstacles, and provide hands‑on support to deliver an exceptional merchant experience.
• Develop repeatable training materials, playbooks, and community engagement strategies that can be scaled to future markets.
• Track and communicate launch progress, merchant engagement, training effectiveness, and other key performance indicators.
• Travel locally, generally within approximately 100 miles of the assigned market, to visit merchants and support training and community events.
• Perform other duties and special projects as assigned.

Qualifications:

• 5–7+ years of experience in merchant success, hospitality, field operations, community management, training, account management, retail, restaurant operations, or another customer-facing environment.
• Proven ability to build authentic relationships quickly with customers, business owners, and community partners.
• Experience working directly with local businesses, restaurants, retailers, or other merchants preferred.
• Experience leading training sessions, workshops, demonstrations, or customer education programs.
• Strong communication, presentation, interpersonal, and relationship-building skills.
• Highly organized, dependable, and capable of managing multiple priorities independently.
• Strong problem-solving skills and a proactive approach to addressing customer and operational challenges.
• Ability to work effectively in a fast-paced, entrepreneurial environment with limited supervision.
• Comfortable balancing strategic planning with hands‑on field execution.
• Willingness and ability to spend significant time traveling locally and working directly with merchants.
• Passion for supporting local businesses and helping independent businesses and communities thrive.