National Regional Account Executive

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
Position Overview

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

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
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
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
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

310+ 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.