Midwest Entertainment Ad Sales Exec

Dow Jones; Chicago (IL); Remote; USD 90,000 - 110,000; Full time

Job summary

Page Six, a leading entertainment news brand, seeks a Chicago-based Account Executive to own the Midwest ad sales territory. You’ll manage a regional book, build client relationships, and close multi-platform advertising deals across digital, social, video, and branded content.

Reporting to the Ad Sales Director, you’ll develop strategic partnerships with agencies and direct clients, drive revenue growth, and help shape innovative advertising solutions while collaborating with internal teams.

Qualifications

• 5+ years of experience in media sales, advertising sales, sales planning, or a related client-facing role.
• Independently manage a sales territory, develop client relationships, and drive revenue growth.
• Experience working with agencies and direct clients in a major market.
• Proven experience selling digital advertising solutions, sponsorships, and/or integrated media packages.
• Familiarity with prospecting and research tools such as MediaRadar, Winmo, or similar platforms.
• Online video sales experience is a plus.
• Entrepreneurial and self-directed with ability to identify opportunities and build a market with autonomy.
• Strong communication, negotiation, and presentation skills.
• Highly organized, accountable, and results-driven.
• A genuine interest in entertainment, celebrity news, and pop culture.

Responsibilities

• Independently own and grow the Midwest sales territory, developing and executing strategies to drive new business and expand existing partnerships.
• Identify, prospect, and convert new business opportunities, building a strong and sustainable regional pipeline.
• Manage the full sales cycle, including outreach, RFP responses, proposal development, pitching, negotiation, and closing.
• Develop and maintain strategic relationships with agency partners and direct clients, serving as a trusted point of contact throughout the partnership.
• Collaborate with internal teams to develop compelling, customized advertising solutions that leverage Page Six’s multi-platform reach.
• Deliver polished, persuasive sales presentations tailored to client objectives and business needs.
• Take ownership of regional revenue goals through proactive pipeline management, account development, and consistent follow-through.
• Monitor competitive activity, industry trends, and market opportunities to identify new avenues for growth.
• Provide exceptional client service, ensuring strong communication and long-term partner satisfaction.

Skills

Midwest sales

Media sales

Agency relationships

Digital advertising

Negotiation skills

Tools

MediaRadar

Winmo

Job description

Page Six, a leading entertainment news brand, seeks a Chicago-based Account Executive to own the Midwest ad sales territory. You’ll manage a regional book, build client relationships, and close multi-platform advertising deals across digital, social, video, and branded content.

Reporting to the Ad Sales Director, you’ll develop strategic partnerships with agencies and direct clients, drive revenue growth, and help shape innovative advertising solutions while collaborating with internal teams.