Junior Sales Rep - Fleet Owl

Territory: South Florida

Company: FleetOwl

Employment Type: Full-Time

FleetOwl is a modern fleet management and operations platform that helps transportation, logistics, and service-based businesses streamline dispatch, tracking, compliance, and fleet performance. We partner with carriers, owner-operators, and fleet operators to reduce costs and improve efficiency through technology.

FleetOwl is looking for a driven Junior Sales Representative to help expand our customer base in the Miami/South Florida region. This role is focused on acquiring new customers through proactive outreach, in-person meetings, and relationship building.

This is an entry-to-mid-level role ideal for someone eager to build a career in B2B sales, learn the fleet and transportation space, and grow into a senior sales position.

• Prospect and identify new fleet customers through cold calling, door-to-door visits, networking, referrals, and local industry events
• Schedule and conduct in-person and virtual product demos
• Build and maintain a sales pipeline within the assigned territory
• Develop relationships with business owners, fleet managers, and operations leaders
• Clearly communicate FleetOwl’s value proposition and assist in closing new deals
• Track activities, leads, and opportunities accurately in CRM
• Work closely with senior sales and onboarding teams to support new customers
• Consistently meet or exceed individual sales goals

• 0–2 years of sales experience (B2B experience a plus, but not required)
• Strong interest in sales, business development, and technology
• Comfortable with cold outreach and face-to-face conversations
• Excellent communication and interpersonal skills
• Self-motivated, coachable, and goal-oriented
• Valid driver’s license and ability to travel locally within South Florida

• Exposure to transportation, logistics, trucking, or fleet operations
• Experience with CRM tools (Salesforce, HubSpot, or similar)
• Bilingual (English/Spanish) strongly preferred due to Miami market

• Base salary plus commission and performance incentives
• Clear path for advancement into a full Sales Representative or Account Executive role
• Mileage or travel reimbursement
• Training, mentorship, and ongoing sales development

• Hands-on sales experience with a real product and real customers
• Opportunity to grow quickly in a fast-scaling company
• Supportive team environment with direct coaching
• Strong product-market fit in a growing industry