Team Lead - Mid-Market Advertising Sales

Within Operations, we are expanding our Digital Inside Sales (DIS) organization to accelerate growth in the SaaS, AI and digital solutions space. Our innovative, data-driven sales model combines trusted technical expertise, cutting-edge technology, and AI-powered insights to help clients transform and scale efficiently. We’re looking for a commercially driven and customer-focused Team Lead to oversee our Advertising Sales Account Managers to manage a portfolio of existing customers. Team Lead - Mid-Market Advertising Sales Responsibilities Lead, coach, and develop a team of high-performing Digital Advertising Account Managers, fostering a culture of continuous learning, innovation, and AI curiosity Drive team performance through clear KPI setting, data-led coaching, and use of AI and analytics tools to optimize pipeline conversion and customer engagement Conduct regular team and one-on-one sessions focused on skill development, sales strategy, and effective use of AI tools for prospecting and personalization Design and implement sales playbooks that leverage AI-driven insights to refine outreach, messaging, and customer targeting across the advertising portfolio Collaborate with Sales and Program leadership to share performance analytics, market intelligence, and customer feedback that inform product and go-to-market strategy Deliver weekly data analysis and performance reports, translating complex metrics into actionable insights Own sales execution and team outcomes, ensuring consistent process adoption, operational excellence, and achievement of revenue growth targets Basic Qualifications Minimum 5 years of experience in Advertising Sales or Advertising Account Management Minimum 2 years of experience managing teams of Advertising Sales or Advertising Account Managers Preferred Qualifications Bachelor's degree Proven ability to coach and inspire performance Strong communication, presentation, and consultative selling skills Highly data-driven, goal-oriented, and comfortable working in a fast-paced environment Familiarity with SaaS products, ad platforms, cloud solutions, and AI-driven sales technologies Knowledge of established sales methodologies (e.g., BANT, MEDDIC) Fluency in data analytics and visualization tools (e.g., Power BI, Tableau) Experience leveraging AI, CRM, Salesforce and prospecting platforms to identify patterns, prioritize opportunities, and enhance team performance This role is full-time in office 5 days a week in Chicago, IL.

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