Advertising Sales Representative

Advertising Sales Representative – Boston, MA & Surrounding Areas

Date Posted: September 23, 2025
Location: Greater Boston, MA
Compensation: $85,000 – $95,000 base salary + 50% bonus potential (first two years guaranteed)
Position Type: Full-time
Travel: ~85% (local/regional travel, home-office based)
Relocation: Not offered
Benefits: Comprehensive medical, dental, auto allowance, and more

About the Opportunity

Ashton North is recruiting on behalf of our client, a trusted media advertising leader for over 20 years, that is expanding its Boston sales team. This is a high-earning career path with uncapped commissions, protected territories, and the ability to sell exclusive advertising solutions inside high-traffic DMV offices.

This is an outside direct sales role, ideal for an energetic, driven advertising professional who thrives in-person with clients and knows the Boston market.

What You’ll Do

• Prospect, cold call, and build new client relationships across the Boston territory.

• Manage and grow an existing account base.

• Sell innovative advertising solutions, including digital, broadcast, and display media, to small, mid-sized, and large companies.

• Travel locally (~85%) while working from a home office.

• Leverage autonomy and protected territories to maximize growth.

What We’re Looking For

• Advertising sales experience in the Boston market is required (radio, TV, digital, print, directory, event, or broadcast).

• Proven ability to hit and exceed sales targets with strong B2B accomplishments.

• 10–15+ years’ experience preferred (mid-career candidates tend to perform best).

• High-energy, self-motivated sales professional with excellent presentation and closing skills.

• Valid driver’s license and reliable transportation.

• Clean driving history — no DWI/DUI within the past 10 years (background checks will be completed).

What’s Offered

• Base Salary: $85K–$95K guaranteed (first 2 years).

• Earning Potential: $150K–$200K+ once established, based on new and renewal billing.

• Benefits: Full package including medical, dental, incentives, and recognition programs.

• Territory: Exclusive, protected Boston territory with high-visibility advertising placements.

• Culture: Long-term stability, with most representatives building 7–20+ year careers here.