Chicago Real Estate Ad Sales Account Executive

Remote; San Francisco (CA); On-site; USD 85,000 - 100,000; Full time

Job summary

The Real Deal is seeking a Sales Account Executive to drive new business for our real estate journalism platform. This Chicago-based role requires a proven track record in advertising and media sales with a consultative approach, handling deals from $10K to $100K per year and growing revenue across local and national advertisers.

You will close new business, manage campaigns, and collaborate across teams to ensure timely ad delivery and accurate billing.

Qualifications

• 3–5 years of advertising/media sales in a client-facing role.
• Proven track record of meeting or exceeding sales goals.
• Strong communication, negotiation, and presentation skills.
• Experience with sales CRMs (HubSpot) and campaign reporting; good grasp of digital media metrics.

Responsibilities

• Prospect, develop, and grow new business across multiple channels: digital, print, and live events.
• Build and manage a robust sales pipeline to meet and exceed targets.
• Use HubSpot CRM to track activity, forecast revenue, and report on sales metrics.
• Collaborate with internal departments to ensure accurate ad delivery, trafficking, and billing.
• Develop strategic account plans in coordination with sales leadership.
• Represent The Real Deal at key industry events and build relationships with decision-makers.

Skills

Advertising sales

Client-facing

Communication

Negotiation

Presentation

Tools

HubSpot CRM

Job description

The Real Deal is seeking a Sales Account Executive to drive new business for our real estate journalism platform. This Chicago-based role requires a proven track record in advertising and media sales with a consultative approach, handling deals from $10K to $100K per year and growing revenue across local and national advertisers.

You will close new business, manage campaigns, and collaborate across teams to ensure timely ad delivery and accurate billing.