Demo

Associate Director, Digital Investment

Kelly Scott Madison
Chicago, IL Full Time
POSTED ON 8/30/2026
AVAILABLE BEFORE 10/15/2026
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...

We’re looking for an Associate Director to lead a cross-channel team. You’ll lead the development of digital strategies and develop POVs. You’ll ensure the integrity of our investment from inception through execution. And you’ll play a key role in organic and new client growth. Your ability to coach, motivate and unify people will pay dividends in the team’s output.

Of course, the person in the role adds the true value—not the role itself—so let’s talk about you and your winning attributes.

Who You Are

  • Strong leadership and communication skills, especially with a bold, challenging client
  • Able to get in the weeds while still thinking strategically at a high level
  • 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
  • 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
  • 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
  • Work in collaboration with cross-channel digital team to 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
  • Partner with Directors and Discipline Leads on client team assignments and workload, alternative revenue streams, new business pitches, and partner relationships
  • Spearhead internal and external industry thought leadership. Have an impactful presence in the ad community to elevate KSM to prospective employees and clients.
  • Maintain a pulse on ever-changing industry trends, programmatic solutions, and emerging technology opportunities to develop POVs and new ways of working to stay ahead of the marketplace

Experience You Should Bring

  • 7 years of experience in digital media investment; social experience desired; cross channel knowledge of paid search & programmatic knowledge a plus
  • Strong social experience, with influencer expertise
  • Pharma and lead gen experience preferred
  • 3 years of management/supervisory experience
  • Experience within media buying systems such as: The Trade Desk, Google Ads, 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
$208,604 to $281,360
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