Associate Director, Media Strategist

The Media team at Pinnacle Advertising is seeking an experienced Associate Director, Media Strategy to lead strategic media planning across a critical Tier 3 Automotive Retail book of business. This role is both a senior strategic leader and a people manager, responsible for overseeing approximately three Senior Media Strategists while elevating the quality, consistency, and innovation of our media product.

This individual will own the development of best-in-class, integrated media strategies and serve as a trusted client partner, internal leader, and mentor. The Associate Director will collaborate closely with buying, operations, analytics, owned media, and technology teams to ensure strategic intent is carried through execution, optimization, and performance storytelling.

What You’ll Do

Strategic Leadership & Client Partnership

• Lead the development of holistic, outcome-driven media strategies across channels including Linear TV, OOH, CTV/OTT, Display, Programmatic, Search, Social, Audio, and Owned Media.
• Own strategic narrative and POV in client meetings, leading media and business discussions with confidence, clarity, and partnership-focused energy.
• Proactively bring forward insights, optimization opportunities, and innovation ideas between meetings, not just during formal presentations.
• Translate data, insights, and marketplace understanding into clear recommendations that drive brand and business performance.
• Support and contribute to new business pitches for Tier 3 automotive opportunities.

Team Leadership & Management

• Directly manage and mentor approximately three Senior Media Strategists, providing coaching, feedback, and career development support.
• Set clear expectations for strategic thinking, output quality, and collaboration across the team.
• Review and guide media strategies, planning decks, and recommendations to ensure consistency, rigor, and excellence.
• Lead training initiatives, including formal training sessions, materials development, and hands-on coaching.
• Foster strong collaboration between strategy, buying, and operations teams to ensure alignment from planning through execution.

Planning, Innovation & Execution Partnership

• Partner closely with media buying and operations teams to ensure plans are executable, optimized, and properly tracked.
• Collaborate with analytics, owned media, and technology teams to evaluate emerging media opportunities and lead ongoing test-and-learn initiatives.
• Champion the use of industry planning tools and data sources to build innovative, insight-led media plans.
• Maintain oversight of budget planning, financial stewardship, and collaboration with invoicing and finance partners.
• Champion internal processes, including budget management, project management workflows, and cross-team collaboration.

Industry & Thought Leadership

• Stay current on emerging media trends, platforms, and vendors, sharing POVs internally and identifying opportunities for agency integration.
• Build and maintain strong relationships with media partners and vendors.
• Act as a senior representative of Pinnacle’s media strategy capabilities with both clients and internal stakeholders.

What You Bring

• 7 years of experience in media planning and/or media strategy, with agency and T3 automotive retail experience required.
• Proven experience leading and mentoring team members in a fast-paced, client-facing environment.
• Deep understanding of campaign planning, activation, and optimization across both traditional and digital media channels.
• Strong proficiency in Google Analytics and Google Ads.
• Advanced ability to assess first-, second-, and third-party data and apply it strategically to drive results.
• Exceptional analytical and storytelling skills, with the ability to turn data into meaningful insights and recommendations.
• Experience managing budgets and partnering closely with finance and operations teams.
• Excellent written, verbal, and presentation skills, with strong proficiency in PowerPoint or Keynote, Excel, and Word.
• Willingness to travel to client locations and industry events as needed, approximately 30 to 35 percent.
• Bonus points if you enjoy Teams, have experience with Airtable or ThoughtSpot, and bring a sense of humor to the work.

Why Pinnacle

Pinnacle’s media strategy team is recognized for deep automotive expertise, strong client partnerships, and a culture rooted in curiosity, collaboration, and innovation. Our clients are hungry for leadership and fresh thinking, and our teams thrive on building relationships, pushing ideas forward, and never settling for average.

BENEFITS OFFERED:

• Stay Healthy: Medical: choose from 3 PPO plans or 1 HDHP with HSA; Dental, Vision
• Feel Secure: Basic Life, Short and Long Term Disability, Legal Plan, ID Theft, Flex Spending Account, Transit benefits
• Work life Balance: Flexible PTO, Paid company holidays, Floating Holiday, Paid Parental and Primary Caregiver leave, Employee Assistance Program (EAP)
• Financial Wellness: Traditional and Roth 401(k) with a company match

Preference is for this role to be based in our Schaumburg, IL office. Our office environment is a key driver of company culture and employee experience, so a regular in-office hybrid model (T-TH in office and M and F remote) is expected for this position.

Equal Opportunity Statement - Pinnacle Advertising is committed to providing equal employment opportunities (EEO) to all employees and applicants without regard to race, color, ancestry, national origin, gender, gender identity, gender expression, sexual orientation, marital status, pregnancy, perceived pregnancy, childbirth, religion, age, disability, genetic information, veteran status, medical condition, or other characteristics protected by state or federal law.