Account Executive (Chicago-Based)

New York Post•Chicago, IL
•$90,000 - $110,000•Remote

About The Position

Page Six is seeking an experienced, Chicago-based Account Executive to join its entertainment advertising sales team. The Account Executive will take ownership of the Midwest market, developing and managing a regional book of business and driving revenue growth through new and existing advertising partnerships. The role reports to the Page Six Ad Sales Director. The Account Executive will build relationships with agency and direct clients and develop multi-platform advertising solutions spanning digital, social, video, and branded content. The position offers autonomy to grow the regional market while collaborating with sales leadership and internal teams. It is remote from the Chicago area, with occasional travel as needed.

Requirements

  • At least 5 years of experience in media sales, advertising sales, sales planning, or a related client-facing role.
  • 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.
  • Experience selling digital advertising solutions, sponsorships, and/or integrated media packages.
  • Familiarity with prospecting and research tools such as MediaRadar, Winmo, or similar platforms.
  • Strong communication, negotiation, and presentation skills, with the ability to build lasting client relationships.
  • Strong organization, accountability, business development, and pipeline management skills; results-driven approach.
  • Interest in entertainment, celebrity news, and pop culture.

Nice To Haves

  • Online video sales experience.
  • Entrepreneurial and self-directed approach, including the ability to identify opportunities and build a market autonomously.

Responsibilities

  • Own and grow the Midwest sales territory by developing and executing strategies for new business and existing partnerships.
  • Identify, prospect, and convert new business opportunities and build a 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.
  • Collaborate with internal teams to develop customized advertising solutions that leverage Page Six’s multi-platform reach.
  • Deliver persuasive sales presentations tailored to client objectives and business needs.
  • Take ownership of regional revenue goals through pipeline management, account development, and consistent follow-through.
  • Monitor competitive activity, industry trends, and market opportunities to identify avenues for growth.
  • Provide exceptional client service and maintain strong communication and long-term partner satisfaction.

Benefits

  • Competitive and flexible compensation.
  • Bonus eligibility.
  • Comprehensive benefits package covering health, retirement, wellbeing, and more.
  • Optional benefits to meet employees’ diverse needs.
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