Head of / Sr. Director of Digital Advertising

Location: U.S. (Remote)

Compensation: $175,000–$225,000 base + performance

Our client, a fast-growing digital media and technology platform operating a large-scale premium indoor screen network across North America, is hiring a senior commercial leader to build and scale its digital advertising division.

This role reports directly to the CRO and President and will focus on launching and expanding a new revenue vertical at the intersection of event-based media and premium indoor digital/DOOH environments.

This is a true builder opportunity.

The Opportunity

Our client operates a network of 10,000+ digital screens across high-traffic, Tier 1 hospitality, convention, and event environments throughout North America.

They are formalizing and aggressively scaling their advertising business and are seeking a senior leader to:

• Develop and own the advertising go-to-market strategy
• Shape pricing, packaging, and long-term growth plans
• Build strategic relationships with brands and agencies
• Drive revenue directly as an individual contributor while the business scales

This is not a mature team leadership role.

This is a build-the-revenue-engine-from-scratch role.

Key Responsibilities

Revenue & Strategy

• Develop and execute a comprehensive ad sales strategy across digital signage and DOOH
• Build pipeline, forecast revenue, and structure complex enterprise deals
• Partner with executive leadership to refine pricing models and product positioning

Direct Sales Execution

• Personally close partnerships with brands and agencies across Digital, OOH/DOOH, CTV, and experiential channels
• Lead pitches, negotiations, and custom proposal development
• Evangelize a premium, event-based advertising network to high-value advertisers

Market Development

• Identify whitespace opportunities within event-driven and experiential advertising
• Represent the company at key industry events and conferences
• Help define a differentiated position within the DOOH landscape

What You Bring

• 8–10+ years of experience in digital advertising, media, DOOH, sponsorship, or related technology sales
• Strong brand and agency relationships
• Demonstrated success closing complex enterprise deals
• Experience shaping GTM strategy and revenue growth plans
• Startup / builder mentality with comfort operating hands-on
• Strong executive presence and communication skills