What are the responsibilities and job description for the Head of Development position at Skyscapes Media?
About Skyscape Media:
Skyscape Media is a next-generation outdoor advertising company, building a portfolio of iconic billboards and urban signage assets across the Southeast. We specialize in high-visibility roadside displays and rooftop digital boards affixed to Class A buildings. We’re creating a brand-forward platform with professional execution, scalable systems, and a long-term ownership mindset.
The Role:
We’re hiring a Head of Development to source and secure new billboard locations. This is a part-time, commission-only role with significant deal-by-deal upside. Ideal for someone with a background at Lamar, Outfront, Clear Channel, or another outdoor operator who wants to work entrepreneurially and participate in the upside of each asset secured.
What You’ll Do:
- Scout, pitch, and negotiate new billboard and signage locations—roadside, digital, and urban
- Lead lease and easement negotiations with landowners and commercial property stakeholders
- Navigate local zoning, signage, and permitting processes
- Maintain strong relationships with landowners, brokers, and municipal contacts
- Report directly to the founder with high autonomy and deal-making flexibility
Who You Are:
- 3–15 years of experience in billboard development, outdoor advertising, or signage permitting
- Background at Lamar, Outfront, Clear Channel, or similar is strongly preferred
- Deep knowledge of Tennessee and/or Southeast regional markets
- Entrepreneurial, proactive, and motivated by results—not titles or structure
- Comfortable working independently and compensated entirely on performance
Compensation:
- 100% commission-based
- Attractive compensation per site secured, with options for long-term participation
- Flexible schedule — work from anywhere, on your own time
Why Skyscape Media:
We’re creating a scalable, brand-led outdoor media platform from the ground up. If you’ve worked inside the billboard industry and want to play offense—not maintenance—this is your chance to build something special with real ownership.