Demo

Associate Director, Digital Investment

Kelly Scott Madison
Chicago, IL Full Time
POSTED ON 4/11/2026
AVAILABLE BEFORE 5/27/2026

Kelly Scott Madison—KSM—is a leading, independent media and advertising agency that futureproofs brands and fuels business growth. Our team of strategists, solutionists, technologists, and data analysts work united alongside incredible brand partners, helping them connect with customers in more meaningful ways today and positioning them to move with the customers of tomorrow. It’s always an amazing and transformative time at our growing media agency.


At KSM, it’s about more than just a passion for our industry and craft. It’s about the impact we make on the lives and livelihoods of those around us, and the highly personal experience we have here. Being an independent, mid-size agency—not too big, not too small, and proudly entrepreneurial—you’ll be empowered, recognized, and challenged to grow here. We’re adding new Bold Builders and uncommon perspectives to our community and can’t wait to learn more about you. But first, let’s explore the opportunity...


Who you are:

  • Razor-sharp, strategic, efficient, and resourceful
  • Decisive, yet open minded and willing to listen patiently
  • Highly regarded for your ability to manage up and down
  • A confident communicator; articulate and engaging
  • An inspirational leader and builder
  • Dedicated to developing and coaching talent through direct feedback
  • Known for having a high-performance drive, a passion for learning and a focus on outcomes
  • Not afraid to get your hands dirty and pitch in when needed
  • A performance marketer with experience in eCommerce and retail who lives and breathes data and numbers
  • Flexible and unflustered; you adapt well to change and pivot with ease


The ways you will make an impact:

  • Collaborate with cross-functional teams to build innovative media strategies that exceed client’s expectations
  • Understand the wholistic digital ecosystem to recommend strategic buying approaches across programmatic, search, and social
  • Develop programs and partnerships that optimize new-to-market opportunities, custom executions, and/or optimal added value elements
  • Ensure media buys are being properly measured to deliver rich insights to our clients
  • Manage team’s work-rate to optimize output and product quality
  • Inspire and develop junior team members through training and coaching, while continuously raising the bar
  • Maintain a pulse on ever-changing industry trends, digital media solutions, and emerging technology opportunities to develop POVs and new ways of working to stay ahead of the marketplace
  • Oversee overall client performance, suggesting tests and optimizations to improve performance over time


Experience you should bring:

  • 7 years of experience in digital media investment; search experience desired; programmatic & social knowledge a plus; experience with eCommerce/shopping ads desired
  • 3 years of management/supervisory experience
  • Experience within media buying systems such as: Google Ads, Microsoft Ads, Skai, The Trade Desk, CM360, Meta, etc.
  • Strong mathematical and organizational aptitude
  • Proficiency with Microsoft Excel and PowerPoint


Benefits we offer:

We've got you covered -- and we’re not just referring to robust health insurance. To us, coverage is about supporting your full experience and whole self, from inclusive benefits, flexibility, and an appreciation for time away, to recognition, professional development, and growth opportunities.

  • Talent Enablement: Career pathing, integrated learning ecosystem, mentorship, and employee recognition
  • Financial: Competitive compensation, 401(k) with company match, pre-tax programs, referral rewards, and a remote work reimbursement
  • Wellness: Comprehensive health insurance (medical, dental, vision, pet, and life), onsite fitness center covered 100%, discounted membership rates at partner gyms and access to virtual fitness classes, Employee Assistance Program (EAP), and curated opportunities to nurture your breaktime
  • Balance: Personalized Paid Time Off (i.e., “Unlimited PTO”), remote work flexibility, paid parental leave (maternity, paternity, and adoption), and a variety of Employee Resource Groups
  • Giving Back: Volunteer opportunities and corporate donation matching through KSM Cares Outreach, our Corporate Social Responsibility program

Salary.com Estimation for Associate Director, Digital Investment in Chicago, IL
$207,363 to $279,677
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