Job Description

Undisclosed Client – National / Regional Account Executive (OOH Media Sales)

Location: Chicago, IL (Remote with Regional Travel)

Our firm has been retained by a rapidly growing outdoor media and advertising company to identify a National / Regional Account Executive to drive revenue growth across Chicago and the broader Midwest region This role is ideal for a highly motivated sales professional with a hunter mentality who thrives on prospecting, opening new business opportunities, and building long-term client partnerships.

This position will focus primarily on new business development with regional brands, retail clients, and media agencies, while expanding the company’s presence across key Midwest markets.

Compensation & Location

• Base Salary: $90,000

• Commission: 6% on all new sales

• Schedule: Monday – Friday, 8:30 AM – 5:00 PM

• Work Arrangement: Remote (home office) with field-based client engagement

• Travel: Regular travel throughout the Midwest region with occasional national travel

The National / Regional Account Executive will be responsible for driving new advertising partnerships and expanding market share across key Midwest markets. The role involves engaging directly with regional brands, retailers, and media agencies to introduce innovative outdoor advertising opportunities across a variety of street-level media formats.

Success in this role requires an entrepreneurial mindset, strong prospecting discipline, and the ability to build relationships with senior marketing and media decision makers.

Key Responsibilities

New Business Development (Primary Focus)

• Conduct proactive outreach including in-person meetings, cold calling, email campaigns, and industry networking

• Identify and secure new regional and national advertising accounts

• Build and manage a robust pipeline of qualified opportunities

• Present outdoor advertising solutions, data capabilities, and market insights to prospective clients

Sales Strategy & Account Growth

• Develop custom proposals, campaigns, and presentations aligned with client marketing objectives

• Collaborate internally to ensure inventory availability, pricing accuracy, and client satisfaction

• Monitor market trends, competitive activity, and emerging advertising categories

• Build strong relationships with agency media planners, strategists, and buyers

Territory Leadership

• Serve as the primary sales leader for Chicago and the Midwest region

• Contribute to national account initiatives and broader sales strategies

• Represent the company at industry events, conferences, and client meetings

Forecasting & Reporting

• Provide regular pipeline updates and revenue forecasts

• Maintain accurate activity and opportunity tracking within CRM systems

• Achieve or exceed quarterly and annual sales targets

Qualifications

Required

• 3–10+ years of B2B sales experience, ideally within media, advertising, or related industries

• Demonstrated success prospecting, pitching, negotiating, and closing new business

• Experience selling to senior decision makers at mid-size to enterprise organizations

• Strong hunter mentality with consistent prospecting activity

• Experience using CRM platforms (Salesforce preferred)

• Excellent communication, presentation, and storytelling skills

• Established network with regional brands or media agencies in the Midwest (Chicago preferred)

Preferred

• Experience selling media, outdoor advertising, transit advertising, or nontraditional media

• Ability to interpret audience data, metrics, and market insights

• Knowledge of the Chicago advertising and agency landscape

• Bachelor’s degree or equivalent professional experience

Benefits

• Comprehensive onboarding and sales training

• Flexible medical benefit options with dental, vision, life, and disability coverage

• Profit-sharing eligibility after one year

• Company-provided work cell phone

• Paid vacation and standard holiday schedule

• Bi-weekly direct deposit payroll

This opportunity offers the chance to build a strong territory, drive significant revenue growth, and work with a highly entrepreneurial sales organization in the advertising industry.