Account Executive (Chicago-Based)

Job Description:

Page Six is one of the most recognized names in celebrity and entertainment news. As the originator of the modern gossip column, we’ve built a brand that keeps audiences in the know, from red carpets and exclusive parties to the biggest headlines in pop culture. Today, Page Six reaches millions across digital, print, social, video, podcast, and TV, meeting our audience wherever they consume content.

We’re looking for a motivated, Chicago-based Account Executive to join our entertainment ad sales team. This role is ideal for an experienced seller with 5+ years of media or advertising sales experience who is ready to take ownership of the full Midwest market and drive meaningful revenue growth. Reporting to the Page Six Ad Sales Director, you’ll develop and manage a regional book of business, building strategic client relationships, identifying new opportunities, and growing advertising partnerships across the territory.

You’ll join a collaborative, high-energy sales team with the opportunity to make a meaningful impact on one of the most recognizable brands in entertainment media. In this role, you’ll have the autonomy to shape and grow the Midwest market while partnering closely with sales leadership and internal teams to develop compelling, multi-platform advertising solutions. You’ll work across digital, social, video, and branded content, bringing Page Six’s extensive reach and cultural relevance to agency and direct clients. This is an opportunity for an entrepreneurial seller to take ownership of a key market, strengthen existing partnerships, and establish new relationships that drive long-term business growth.

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

The ideal candidate will have/be:

• 5+ years of experience in media sales, advertising sales, sales planning, or a related client-facing role
• Demonstrated ability to 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 the ability to identify opportunities and build a market with a high degree of autonomy
• Strong communication, negotiation, and presentation skills, with the ability to build lasting client relationships
• Highly organized, accountable, and results-driven, with strong business development and pipeline management skills
• A genuine interest in entertainment, celebrity news, and pop culture

Please note: this role will work remotely out of the Chicago area with occasional travel as needed.

Equal Opportunity Employer

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin, protected veteran status, disability status or any other protected characteristic under applicable law. EEO/Disabled/Vets

Reasonable Accommodation

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Base Pay Range: $90,000 - $110,000 + bonus

We’re committed to offering competitive and flexible compensation to attract top talent. This pay range reflects our good faith estimate for the role and may vary based on a candidate’s experience, skills, location, and other relevant factors.

For bonus-eligible roles, targets are determined based on multiple considerations, including market benchmarks and individual contributions.

For benefits-eligible roles, we offer a comprehensive and competitive benefits package covering health, retirement, wellbeing, and more, along with optional benefits to meet the diverse needs of our employees