Remote Chicago Entertainment Ad Sales Exec

Page Six

Chicago (IL)

Remote

USD 90,000 - 110,000

Full time

47 hours ago
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Job summary

Page Six, Chicago-based, is seeking an Account Executive to own and grow the Midwest ad sales territory. You will lead agency and direct client relationships, selling digital, social, video, and branded content solutions across platforms.

The role offers remote work with occasional travel and a path to drive substantial revenue in a recognizable entertainment brand. The ideal candidate has over 5 years in media or ad sales, a proven ability to build a regional book of business, and strong

Qualifications

  • 5+ years of experience in media sales or advertising sales.
  • Ability to independently manage a Midwest sales territory.
  • Experience selling to agencies and direct clients in a major market.
  • Proven experience selling digital advertising solutions and packages.
  • Familiarity with prospecting tools like MediaRadar or Winmo.
  • Online video sales experience is a plus.
  • Entrepreneurial, self-directed, with strong communication and closing skills.

Responsibilities

  • Own and grow the Midwest sales territory and revenue targets.
  • Identify, qualify, and close new business opportunities.
  • Manage full sales cycle: outreach, RFPs, proposals, pitches, negotiations, closing.
  • Build strategic relationships with agencies and direct clients.
  • Collaborate with internal teams to create multi-platform ad solutions.
  • Deliver persuasive presentations aligned with client objectives.
  • Drive pipeline, account development, and consistent follow-through.
  • Monitor market trends and competitive activity for growth.
  • Provide exceptional client service and long-term partnerships.

Skills

Media sales experience
Digital ads sales
Agency & direct clients
MediaRadar/Winmo
Video sales
Entrepreneurial
Communication & negotiation

Job description

Page Six, Chicago-based, is seeking an Account Executive to own and grow the Midwest ad sales territory. You will lead agency and direct client relationships, selling digital, social, video, and branded content solutions across platforms.

The role offers remote work with occasional travel and a path to drive substantial revenue in a recognizable entertainment brand. The ideal candidate has over 5 years in media or ad sales, a proven ability to build a regional book of business, and strong

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