Our client is an independent, digitally-led media organization operating at significant scale and known for its depth in programmatic, omnichannel retail, and full-funnel media execution. Managing a large portfolio of digital investment, the company partners closely with major brands through a selective partner model that emphasizes efficiency, service, and the ability to move at the speed of modern retail.

As the organization strengthens its operational infrastructure and prepares for continued growth, it is hiring a Head of Media Investment to lead investment operations across digital, programmatic, and omnichannel channels. This is a highly unique role—much more inward-facing than the typical senior investment title—focused on deep digital expertise, rigorous operational execution, and elevating the quality, consistency, and performance of the investment discipline.

This leader will have wide remit across team utilization, workflow design, QA, partner engagement, and the systems and controls necessary to deliver flawless buying at scale.

This is a hybrid role with regular travel to Chicago.

Position Responsibilities

• Lead all digital and programmatic investment execution, including activation, pacing, optimization, QA, and reconciliation.
• Oversee workflow and handoff processes between planning, analytics, investment, and operations.
• Build and refine operational frameworks, SOPs, dashboards, and performance governance.
• Ensure efficient utilization and deployment of media buyers and investment staff.
• Serve as the organization’s senior-most digital and programmatic expert—hands-on, technical, and execution-driven.
• Evaluate DSPs, data partnerships, marketplaces, and advanced audience strategies.
• Manage a highly curated set of media partners; ensure service levels, accountability, and strategic alignment.
• Leverage opportunistic inventory opportunities within a fast-moving retail ecosystem.
• Inspire new thinking, introduce modern buying approaches, and continually improve processes.
• Lead and mentor a large investment team; promote a culture of precision, rigor, and operational excellence.

Position Qualifications

Required:

• 12+ years of experience in media investment, with heavy emphasis on digital and programmatic.
• Deep, hands-on command of activation — not a conceptual or purely external-facing leader.
• Proven ability to run a complex investment operation at meaningful scale.
• Strong process builder able to implement structure, controls, and systems of accountability.
• Experience in independent agencies or high-utilization environments with fast execution cycles.
• Expertise across DSPs, audience buying, retail media, and first-party data activation.
• Ability to elevate teams and drive consistent, high-quality execution.
• Comfortable in an inward-facing role that prioritizes rigor, improvement, and operational depth.

Talentfoot Overview

Talentfoot Executive Search specializes in future-proofing organizations by securing forward-thinking leaders across marketing, sales, eCommerce, media, product, data, and technology. With a 98% success rate and 2,500+ client partnerships since 2010, Talentfoot connects brands with transformative leadership. Learn more at Talentfoot.com.

Apply Today

This is a rare opportunity to shape the investment operations of a digitally-driven media organization with significant scale.

If you are a digital investment leader with deep programmatic expertise and a passion for operational excellence, apply today to lead the future of media investment.