Field Sales Representative

The Planet Group; Portland (OR); On-site; USD 65,000 - 90,000; Full time

Job summary

The Planet Group is seeking a dynamic Merchant Success field representative to partner with local restaurants, retailers, and community partners across Portland and surrounding areas. You will travel locally to onboard, train, and support merchants, building lasting relationships and driving activation and retention.

In this hands-on role, you will lead training sessions, host workshops, and collaborate with Product, Operations, and GTM teams to ensure successful market launches and ongoing

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.

Responsibilities

• Build trusted relationships with local merchants, business owners, managers, and frontline staff.
• Serve as the primary field representative for Neighborhoods 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 identify opportunities to improve participation.
• Partner with Product, Operations, Go-to-Market, and Account Management teams to support 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 KPIs.
• 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.

Skills

Relationship building

Public speaking

Communication

Organization

Problem-solving

Travel readiness

Job description

• Build trusted relationships with local merchants, business owners, managers, and frontline staff.
• Serve as the primary field representative for Neighborhoods 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.