Outside Sales Representative – Billboard Advertising

Central Florida Focus

We are a fast-growing outdoor advertising company with over 350 billboard locations across Central Florida, adding new inventory every month. We’re hiring Outside Sales Representatives to build, develop, and grow new business in the Ocala and surrounding markets

This is a true hunter role designed for individuals who want autonomy, uncapped earning potential, and the opportunity to build a long-term book of business.

What You’ll Do

• Prospect daily for new advertising clients (this is the majority of the role)
• Sell billboard advertising solutions to local and regional businesses
• Conduct face-to-face meetings with business owners and decision-makers
• Build your book of business from the ground up
• Accounts may be reassigned over time as territories mature
• Track activity and manage your pipeline using CRM tools
• Create proposals and close new business
• Maintain a strong presence in the market through networking and outreach

Training & Ramp-Up

• Sales resources and onboarding support provided
• Ongoing coaching and hands-on training
• Approximately 90+ days to build pipeline and early momentum
• Performance evaluated based on activity levels, pipeline development, and consistency

Compensation & Benefits

• Base+Commission Structure
• 401(k) plan
• Full benefits package
• Car allowance
• $0.30 per mile mileage reimbursement
• Expense-paid client meals and business dinners
• Significant income upside as inventory and territory grow

Territory & Location Requirements

• Openings available in Ocala and Lakeland
• Candidates for the Ocala territory must live within 20 minutes of Ocala
• Field-based, outside sales position
• High degree of autonomy once established

Who We’re Looking For

• Candidates with experience must show proven sales results
• More tenured candidates should demonstrate job stability and longevity
• Self-motivated, disciplined, and comfortable working independently
• Resilient and comfortable with cold prospecting and rejection
• Organized, accountable, and goal-driven
• Strong desire to build and grow something long-term

(Bryce Ballard with Express Employment Ocala is the primary point of contact for this position. Please apply for more information.)