DIGITAL MEDIA EXECUTIVE (REMOTE CHICAGO) - KWQC

About the Company

Gray Media is a growing multimedia company headquartered in Atlanta, Georgia, and the nation's largest owner of top-rated local television stations and digital assets. We serve 117 full-power television markets, reaching approximately 37% of US television households. Our portfolio includes 80 markets with the top-rated television station and 100 markets with the first and/or second highest-rated station. We also own the largest Telemundo Affiliate group with 47 markets and Gray Digital Media, a full-service digital agency offering advanced digital marketing strategies and products. Additional media properties include video production companies Raycom Sports, Tupelo Media Group, and PowerNation Studios, as well as studio production facilities Assembly Atlanta and Third Rail Studios.

About the Role

This is a digital-first, remote sales role focused exclusively on selling Gray Digital Media's full suite of advanced digital marketing solutions to businesses in the Chicago market. The ideal candidate is a self-starter who thrives in an autonomous environment, is passionate about new business development, and has a strong command of digital advertising strategies. Success will be measured by high sales activity—prospecting, new client meetings, and customized proposals—while building a strong and growing book of business in the Chicago region.

Responsibilities

• Prospect and develop new business across multiple industries in the Chicago metro and surrounding communities, actively seeking and winning new client opportunities.
• Consult with business owners, marketing executives, and decision-makers to develop and implement effective digital marketing strategies tailored to their business goals.
• Sell and grow Gray Digital Media's full suite of digital advertising products, including OTT/Streaming (Connected TV), Programmatic Display & Video, Targeted Email Marketing, Paid Social Media, YouTube Advertising, Search Engine Marketing (SEM) & Search Engine Optimization (SEO), and more.
• Design, write, and present custom marketing proposals and presentations that clearly communicate digital solutions and demonstrate measurable ROI for clients.
• Meet and exceed sales activity targets, revenue goals, and budgets, managing a growing book of business across the Chicago region.
• Develop, retain, and grow strong client relationships through consistent in-person consultation, strategic planning collaboration, and ongoing campaign performance reviews.
• Use client management tools and reporting software to track performance, optimize campaigns, and demonstrate ROI to clients.
• Collaborate effectively with internal teams, including digital strategists, creative services, and the KWQC/Gray Digital Media sales team in Davenport, to deliver top-tier client campaigns.
• Learn and master Gray Digital Media's advertising platform and stay current on emerging digital marketing trends and products.
• Adapt to varying work schedules, including occasional meetings or events outside regular business hours.

Requirements

• Energetic, self-motivated professional with a passion for new business development and digital marketing solutions.
• Strong communication, presentation, and negotiation skills—ability to consult confidently with business owners and marketing decision-makers.
• Proven ability to work independently and manage time effectively in a remote work environment.
• Strategic thinker with strong organizational skills and the ability to manage multiple client relationships simultaneously.
• Proficiency with Microsoft Office (Word, Excel, PowerPoint) required; experience with CRM/client management tools preferred.
• Valid driver's license and good driving record required—regular in-person client calls throughout the Chicago region are expected.
• Prior experience in digital media sales, advertising, or marketing is a plus—but we provide comprehensive training to support your growth and success.

Benefits

• Comprehensive Medical (Rx), Dental, and Vision Coverage
• Health Savings Account with Company contributions
• Flexible Spending Account
• Employer-paid life and disability benefits
• Paid parental leave benefits
• Adoption and Surrogacy Benefits
• 401(k) Plan, including matching and profit-sharing contributions
• Employee Assistance Program
• Voluntary benefits, including Hospital Indemnity, Critical Illness, Accident Insurance, and supplemental life insurance coverage
• Paid Time Off, including Relocation PTO

Pay

Salary + Commission

Schedule

Monday - Friday, 8:00 AM - 5:00 PM