Territory Sales Representative - Orlando, FL

Territory Sales Representative

We are a rapidly growing technology company specializing in point-of-sale payment processing and delivery integrations for locally owned brick-and-mortar stores. Our mission is to accelerate the transition from traditional electronic cash registers to powerful new point of sale products. Our highly specialized systems address the specific pain points identified through over a decade of working with neighborhood stores, markets, and restaurants. With an unrivaled dedication to delivering superior tools that are easy to use and a technical team providing industry-leading support, our systems open the door to the next level of success for our clients.

POS360 is seeking a Territory Sales Representative to join our growing field sales team. This role is essential to expanding our footprint within independent retail, particularly liquor and off premise accounts by building trusted relationships and delivering value-focused solutions.

You will own your territory end-to-end, from prospecting and in-store demos through installation, activation, and ongoing account growth. Working closely with company leadership and cross-functional teams, you'll play a key role in strengthening client relationships and accelerating POS360's growth in the market.

This is an excellent opportunity for a highly motivated, independent self-starter who thrives in face-to-face sales, understands the rhythm of independent retail, and sells through relationships rather than discounts.

Territory Development & Field Sales Execution

• Prospect and grow a territory through cold and warm in person outreach to independent liquor and retail stores
• Walk into stores daily to introduce POS360 solutions
• Build and manage a robust pipeline using CRM tools and personal industry relationships

Product Demos & Client Enablement

• Conduct in-store demonstrations of POS360 portfolio of products and solutions through various platforms and media
• Clearly articulate customer pain points and position POS360 as a revenue driving solution
• Train store owners, managers, and cashiers on POS systems, ancillary products, and services

Account Ownership & Relationship Management

• Own client relationships from first conversation through installation, activation, and long-term success
• Maintain regular contact with clients, gather feedback, and identify upsell or expansion opportunities
• Resolve customer issues by partnering with Client Services, Deployment, and Operations teams

Sales Operations & Market Intelligence

• Negotiate pricing and terms; prepare agreements and close deals
• Maintain accurate CRM notes, call reports, territory plans, and performance reporting
• Monitor competitor activity, market trends, and delivery platform dynamics (DoorDash, Uber Eats, Instacart)
• Recommend product, service, or policy improvements based on field insights

Collaboration & Leadership Engagement

• Work closely with Marketing, Procurement, Client Services, and Deployment teams to ensure smooth execution
• Report weekly to leadership and participate in Monday team syncs
• Contribute to a high-performance, collaborative sales culture

Qualifications

• 3+ years of sales experience; liquor, beverage, or off premise retail sales experience highly preferred
• Demonstrated success in value based, relationship driven sales
• Experience calling directly on independent retail decision makers
• Familiarity with CRM tools and maintaining accurate activity records
• Proficient with office software and phone systems

Preferred Education & Skills

• BA/BS degree in Marketing, Business Administration, Advertising, or a related field
• Bilingual: Fluent in English and Spanish or Arabic
• Interpersonal, negotiation, and presentation skills

Benefits

• 401(k) matching
• Dental insurance
• Health insurance
• Vision insurance
• Paid time off
• Flexible working hours
• Free on-site gym access

Position is full-time and remote and can be located a few cities/states: Orlando, FL areas. Compensation: $75,000 base + Commission OTE $195,000 no cap

POS360, Inc, Is A Drug Free Workplace Please note that POS360 is a drug-free workplace and all candidates are required to undergo a pre-employment drug screening before being fully employed. This policy is in place to ensure the safety and health of all employees.

POS360, Inc. Is An Equal Opportunity Employer Equal access to programs, services and employment is available to all persons. Those applicants requiring reasonable accommodation to the application and/or interview process should notify a representative of the Human Resources Department.