Position Title: Managing Director, Media Investments
Location: Toronto / Ottawa / Remote Hybrid
Reports To: Founder / Executive Committee
Compensation: Deferred competitive salary with performance-linked incentives and equity participation
Search Mandate: Yorktown Search Partners is conducting a confidential executive search on behalf of a private client in the media investment and strategic growth sector.

Overview

Yorktown Search Partners has been retained to recruit a Managing Director, Media Investments for a confidential client operating at the intersection of media, venture investing, and creative brand strategy. The firm specializes in acquiring and partnering with consumer-facing media assets, as well as structuring media-for-equity transactions that drive scale and long-term value.

This is a senior leadership opportunity for an experienced dealmaker with fluency in both capital markets and modern media ecosystems. The successful candidate will lead origination and execution of investment mandates, contribute to portfolio strategy, and help shape a next-generation investment platform focused on innovation and value creation.

Compensation includes a market-driven deferred base salary, equity ownership, and upside through revenue participation and carried interest.

Key Responsibilities

Investment Strategy & Origination

• Develop and lead the media investment roadmap, targeting digital platforms, content companies, creator-led brands, and media-for-equity structures
• Originate proprietary deal flow through relationships with founders, platforms, brand strategists, and agency groups
• Evaluate potential partnerships through strategic, financial, and operational lenses

Transaction Execution

• Lead all stages of investment execution: term sheets, valuation modeling, diligence, negotiation, and structuring
• Oversee internal analysts, external counsel, and diligence partners to maintain disciplined execution standards
• Develop integration plans and contribute to ongoing growth strategy post-close

Portfolio & Ecosystem Development

• Actively support portfolio companies as a strategic partner-providing governance, strategic input, and operational insight
• Cultivate partnerships across the venture, creative, media, and technology ecosystems to support syndication, monetization, and expansion
• Elevate the firm's profile through thought leadership, event participation, and ecosystem storytelling

Ideal Candidate Profile

• 7-12+ years of experience in investment banking, venture capital, private equity, or media corporate development
• Demonstrated success leading end-to-end transaction processes and closing strategic deals
• Deep understanding of media monetization models, advertising dynamics, creator platforms, and branded content
• Networked across content creators, digital platforms, agencies, and consumer media brands
• Commercially strategic with strong quantitative skills and creative fluency
• Entrepreneurial and self-directed, with a passion for innovation in media and investments

Compensation & Alignment Structure

This is a principal-track leadership role with access to:

• A market-aligned deferred salary, structured in line with platform maturity and performance
• Performance-based incentives linked to deal execution, revenue contribution, and portfolio value creation
• Meaningful equity ownership and participation in carried interest and media-for-equity upside

Full compensation terms will be shared with shortlisted candidates under NDA.