Digital Strategy Associate Jobs in Chicago, IL (NOW HIRING)

Please note that we will never request payment or bank account information at any stage of the recruitment process. As we continue to grow our teams, we urge you to be cautious of fraudulent job postings or recruitment activities that misuse our company name and information. Please protect your personal information during any recruitment process. While Monks may contact potential candidates via LinkedIn, all applications must be submitted through our official website (monks.com/careers).
About the Role
The Media Strategy department is the strategic heart of Monks' media offering: a unified team bringing together deep expertise in media strategy, media planning, and account management. We build integrated, full-funnel media strategies that connect brand storytelling to measurable business outcomes, powered by AI-enabled workflows and analytical rigor.
Responsibilities:
The Associate Director, Media Strategy leads key strategy and planning workstreams on one of Monks' most important client relationships: owning deliverables end to end and serving as a trusted day-to-day client contact. This requires:

• Strong ability to build client and platform relationships
• A track record of managing and growing account workstreams
• Ability to tell data-driven stories and extract key insights for senior-level clients
• Full-funnel understanding of the media landscape across Social, Search, Programmatic/Digital Investment, Holistic Video, OOH, and Direct Partnerships.
• Experience managing and stewarding career growth for direct reports
• Serve as a lead day-to-day point of contact with media client stakeholders.
• Develop go-to-market strategies and integrated, full-funnel media plans informed by rich consumer and industry insights with a laser focus on outcomes.
• Lead briefings, brainstorms, presentations and reporting calls to represent and support the team.
• Prepare executive-level deliverables on performance, strategic POVs and competitive analysis.
• Analyze data, craft insights and make recommendations internally and externally in deck form.
• Use AI-enabled tools to accelerate research, insight generation, plan development and reporting.
• Maintain executional and performance excellence through ongoing collaboration with Activation, Investment and Data & Measurement teams.
• Establish relationships with platform partners to stay current on offerings and maximize media value.
• Track and manage the client scorecard to ensure the team is set up to hit performance goals.
• Lead and manage 1-3 direct reports; regularly meet to establish priorities and offer guidance and feedback.

About You
The essentials:

• 7+ years of industry experience focused on media strategy, planning and client service.
• B2B experience is required
• Eager to forge long-term client partnerships built on mutual trust and fueled by ongoing performance.
• Proficient in media strategy with experience across digital direct, programmatic, social and search plus fluency in brand and offline channels.
• Ability to craft compelling, data-driven narratives for client deliverables.
• Experienced with syndicated planning and competitive insight tools (e.g., Comscore, GWI, Pathmatics, Nielsen).
• Comfortable adopting AI-enabled tools and helping the team work smarter.
• Excellent written and verbal communication skills; desire to grow as a leader and mentor.
• BA or equivalent with emphasis on marketing, advertising, or business.

At Monks, we believe in fostering an environment where a diversity of perspectives can thrive. We proactively work to design hiring processes that promote equity and inclusion while mitigating bias. We celebrate diversity and are committed to building a team that reflects the communities we serve. We welcome and encourage qualified applicants, from all backgrounds, who are excited to contribute to our mission.
#LI-OG1
#LI-Hybrid
What We Offer
Benefits

• Excellent, full coverage medical, dental, and vision insurance - more about our coverage here!
• Generous PTO and 15 company-wide holidays
• 401k with company contribution
• Paid parental leave
• Work-life balance with an emphasis on personal well-being
• Career growth in a disruptor space & entrepreneurial opportunities within the Monks network
• A globally diverse & inclusive culture with employee resource groups such as S4 Melanin, Pride.Monks, Cultura.Monks, and more!
• Authentic commitment to DEI efforts and sustainable growth. (Why Sir Martin Sorrell signed The Climate Pledge here!)

This role is subject to our Return to Office (RTO) policy. If you reside within a commutable distance of one of our office locations, you will be expected to work from the office a set number of days per week. The specific details, including the number of required office days, will be in accordance with the company's then-current RTO policy, which is subject to change from time to time.
Monks has provided a compensation range that represents its good faith estimate of what Monks may pay for the position at the time of posting. Monks may ultimately pay more or less than the posted compensation range. The salary offered to the selected candidate will be determined based on job-related factors, but not based on a candidate's sex or any other protected status.
Salary Range:
$100,000-$110,000 USD
About Monks
Monks is the global, digital-first, data-driven, unitary operating brand of S4 Capital plc. With a legacy of innovation and specialized expertise, Monks combines an extraordinary range of global Marketing and Technology Services to redefine how brands interact with the world. Through Monks.Flow, its flagship AI ecosystem for marketing orchestration, Monks transforms marketing into a growth engine, collapsing timelines and connecting brands to culture in real time. By deploying bespoke intelligent agents across disciplines and delivering culturally relevant, high-impact creative and digital solutions, Monks solves key critical business challenges across the entire brand enterprise to help brands sustain long-term impact.
Monks was named a Contender in The Forrester Wave™: Global Marketing Services, ranks among Cannes Lions' Top 10 Creative Companies (2022-25) and remains the only partner featured in AdExchanger's Programmatic Power Players list every year (2020-24). Named Adweek's first AI Agency of the Year (2023) and The One Show's inaugural AI Pioneer Organization, Monks was also awarded Business Intelligence Group's 2025 Excellence in Artificial Intelligence Award in both the Organizational and AI Product categories. As a trusted partner to cutting-edge innovators in tech, Monks earned titles such as Optimizely Experimentation Partner of the Year (2025), runner-up for the Adobe Firefly Partner Award (2024), and Workato's AI Visionary Customer Impact Award (2024). Additionally, Monks achieved a record-breaking number of FWAs and continues to hold the most of any partner.
We are an equal-opportunity employer committed to building a respectful and empowering work environment for all people to freely express themselves amongst colleagues who embrace diversity in all respects. Including fresh voices and unique points of view in all aspects of our business not only creates an environment where we can all grow and thrive but also increases our potential to produce work that better represents-and resonates with-the world around us.