Associate Director, Investment

Kelly Scott Madison•Chicago, IL

1d•Hybrid

About The Position

Kelly Scott Madison (KSM) is seeking a dynamic, strategic, and people-centered Associate Director, Investment to help shape the next chapter of local investment excellence. This role is ideal for a media investment leader who knows how to turn strategy into action, build trusted relationships, and elevate both the work and the team. You’ll play a key role in leading local Video & Audio investment and supporting Out-of-Home strategy, partnering across disciplines to deliver smart, scalable solutions that drive strong client outcomes and continued agency growth. If you’re energized by building smarter investment strategies, strengthening partner and client confidence, and mentoring talent in a fast-moving, collaborative environment, this is an opportunity to make visible impact while growing your leadership footprint at KSM. As an Associate Director, Investment, you will help lead the strategic development and stewardship of KSM’s local Video & Audio investment practice, while also supporting broader local investment initiatives including Out-of-Home. This is a leadership role for someone who can confidently guide investment strategy, raise the standard of execution, and create clarity across complex client and marketplace dynamics. You will partner closely with planning, client leadership, and media partners to develop performance-driven recommendations, build scalable frameworks, and identify opportunities that strengthen outcomes for clients while advancing KSM’s investment capabilities.

Requirements

7+ years of local media buying, investment, or related experience within a media agency or similar environment, with strong depth in Linear Video & Audio and additional exposure to Streaming and Out-of-Home a plus.
3+ years of people leadership experience, with a demonstrated ability to coach, motivate, and develop high-performing teams.
Strong expertise in local media strategy, investment stewardship, negotiation, and performance analysis, along with the judgment to make smart, balanced decisions in a fast-moving environment.
Hands-on experience with media buying systems such as Mediaocean (Spectra OX and Prisma) and common industry tools including Nielsen, SQAD, and SRDS.
Strong analytical and mathematical aptitude, with the ability to interpret performance data, uncover insights, and translate findings into actionable recommendations.
Excellent communication, organization, and cross-functional collaboration skills, along with proficiency in Microsoft Excel, Word, PowerPoint, and monday.com.

Nice To Haves

Established relationships with vendors, partner management teams, and media representatives preferred.

Responsibilities

Lead local investment strategy across assigned business, with a focus on Video & Audio and support for Out-of-Home, ensuring recommendations are aligned to client goals, audience insights, and market opportunity.
Partner with planning, client leadership, and activation teams to translate strategy into clear investment direction, practical frameworks, and high-quality execution.
Provide leadership across pre- and post-buy stewardship, schedule analysis, proof-of-performance, and optimization recommendations to ensure investment rigor and accountability.
Help advance pricing standards, negotiation strategy, and investment governance to improve consistency, value creation, and scalable ways of working across the discipline.
Build trusted relationships with media partners and internal stakeholders to identify new opportunities, solve challenges quickly, and support smarter investment decisions.
Coach and develop team members through hands-on leadership, clear feedback, and ongoing capability building that strengthens both individual growth and team performance.
Stay fluent in marketplace shifts, emerging partners, and evolving local media opportunities to bring fresh, forward-looking thinking to clients and KSM teams.