Territory Sales Representative- Florida

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.

About the role

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.

Responsibilities

• 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
• 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
• 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
• 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
• 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

Pay

$75,000 base + Commission OTE $190,000 no cap

Schedule

Position is full-time and remote and can be located in the following areas: Miami, Orlando, Tampa, or Jacksonville, FL.

POS360 is a drug-free workplace and all candidates are required to undergo a pre-employment drug screening.