Media & Advertising Sales Leader

Summary

Join We Are Rosie as a Media Operations & Ad Sales Lead to build and formalize direct ad sales offerings for a leading retail and payments company. You will create a comprehensive Media Kit, Sell Sheets, and an RMN playbook, consulting with senior leadership to develop monetization frameworks for on-property media inventory. This role requires collaboration, strategic thinking, and execution in a fast-paced environment. The position is remote, preferably in the Central Time Zone, with a duration of approximately 5-6 weeks. The hourly rate is $110, and the work involves approximately 30 hours per week. You will be responsible for developing strategic frameworks, creating sales materials, consulting with leadership, building relationships, and ensuring cross-functional team alignment.

Requirements

• 7+ years of experience in media strategy, ad sales, or media operations — experience across agency, platform, publisher, or client-side roles is relevant
• Proven track record of developing successful media kits, ad sales materials, and advertising solutions
• Strong communication, presentation, and relationship-building skills
• Ability to collaborate across functions, influence stakeholders, and deliver high-quality client-facing materials
• Deep understanding of Retail Media Networks, ad sales strategy, and cross-channel marketing approaches
• Proficiency in media planning, analytics, and reporting best practices

Responsibilities

• Develop a strategic framework for client's on-property media inventory and marketplace offerings
• Lead the creation of a formal Media Kit, Sell Sheets, internal/external training materials, and an RMN playbook for client marketing teams
• Consult with SVP, Performance Marketing Demand Generation and other leadership to deliver comprehensive media recommendations and strategic deliverables
• Build and nurture relationships with internal stakeholders and external partners to support business growth and advertising sales opportunities
• Effectively communicate and collaborate with cross-functional teams including Product, Ad Operations, and Media to ensure accuracy, alignment, and efficiency
• Take ownership of daily deliverables, proactively addressing needs and solving challenges before they arise
• Contribute to conversations about media upsell opportunities, efficiencies, and strategic alignment across teams
• Lead the development and ongoing updates of media kits tailored to various market segments, incorporating audience insights, success stories, and competitive differentiators
• Provide thought leadership around ad sales strategy, Retail Media Networks, people-based targeting, and emerging Martech applications
• Maintain business acumen by working closely with product and media teams to ensure monetization strategies and financial accuracy

Preferred Qualifications

• Experience navigating regulated industry categories is a plus
• Remote (preferred availability in Central Time Zone; proximity to Stamford, Chicago, or Atlanta is a plus)
• ~5–6 weeks
• $110/hr
• ~30 hrs