Director of Sales, Insights & Activations

The Director of Sales, Insights & Activations is responsible for driving advertising revenue growth across the 365 Retail Markets media network. This role leads the sales strategy, pipeline development, and execution of direct advertising sales efforts, connecting brands, agencies, and strategic partners with one of the largest digital retail media networks in unattended retail.

The Director will be accountable for acquiring new advertisers, growing existing media partnerships, and maximizing revenue opportunities across 365’s in-store digital screens, promotional channels, and media offerings. This individual will serve as a key leader in building and scaling the 365 Media business, establishing market presence, and creating long-term relationships with advertisers seeking to reach convenience, workplace, and foodservice consumers.

Responsibilities

Revenue Generation & Sales Leadership

• Own and exceed annual advertising revenue targets for 365 Insights & Activations. 
• Develop and execute a comprehensive sales strategy focused on direct advertising sales. 
• Build and maintain a robust pipeline of advertisers, agencies, brands, and media buyers. 
• Negotiate and close advertising agreements, sponsorships, promotional campaigns, and strategic media partnerships. 
• Identify new revenue opportunities and advertising products to increase media network monetization. 
• Build, lead, and scale the 365 Insights & Activations sales organization by recruiting, developing, and mentoring high-performing sales talent to support the growth of advertising, data, and activation revenue streams. 
• Establish the sales structure, processes, and performance metrics necessary to expand the team over time, partnering with executive leadership to identify future headcount needs and organizational growth opportunities.

New Business Development

• Prospect, engage, and secure new advertiser relationships across key consumer packaged goods (CPG), foodservice, beverage, convenience retail, and emerging categories. 
• Develop strategic relationships with media agencies and advertising decision-makers. 
• Create customized advertising solutions that align advertiser objectives with 365 Media capabilities. 
• Expand market awareness and position 365 Insights & Activations as a leading retail media network. 

Account Growth & Retention

• Manage strategic advertiser relationships to drive renewals and recurring revenue. 
• Conduct regular business reviews with advertising partners to demonstrate campaign performance and ROI. 
• Identify upsell opportunities including expanded screen placements, promotional programs, audience targeting, and data-driven advertising solutions. 
• Ensure high levels of customer satisfaction and long-term partnership success. 

Media Strategy & Product Development

• Partner with Product, Marketing, Analytics, and Operations teams to develop compelling media offerings. 
• Provide market feedback on advertiser needs, industry trends, and competitive positioning. 
• Help define pricing strategies, inventory packaging, sponsorship opportunities, and sales programs. 
• Collaborate on the development of audience measurement, attribution, and reporting capabilities. 

Team Leadership & Cross-Functional Collaboration

• Build, lead, and mentor a high-performing media sales organization as the business grows. 
• Establish sales processes, performance metrics, forecasting standards, and pipeline management disciplines. 
• Collaborate closely with Marketing, Customer Success, Operations, and Executive Leadership to ensure successful campaign execution. 
• Present business performance, forecasts, and strategic recommendations to senior leadership. 

Industry Representation

• Represent 365 Media at industry conferences, trade shows, client meetings, and advertising events. 
• Develop thought leadership and market presence within the retail media and digital advertising industries. 
• Build strategic partnerships that enhance the reach and value of the 365 Media platform. 

Qualifications

Required

• 8+ years of experience in advertising sales, media sales, retail media, digital media, sponsorship sales, or related fields. 
• Proven track record of achieving and exceeding revenue targets. 
• Experience selling directly to brands, advertisers, and media agencies. 
• Strong network of relationships within advertising, CPG, retail, or agency communities. 
• Demonstrated success in building and managing a sales pipeline from prospecting through close. 
• Exceptional negotiation, presentation, and relationship management skills. 
• Strong analytical and business acumen with the ability to translate campaign performance into business value. 

Preferred

• Experience selling retail media, digital out-of-home (DOOH), in-store media, programmatic advertising, or shopper marketing solutions. 
• Knowledge of convenience retail, foodservice, workplace dining, vending, or unattended retail industries. 
• Experience launching or scaling a media network business. 
• Familiarity with advertising measurement, attribution, audience analytics, and campaign reporting platforms.