Chief Legal Officer / Head of Legal Advisory - Jobs in Toronto

Job Description

Position Title: Chief Legal Officer / Head of Legal Advisory Location: Remote / Hybrid Reports To: Managing Partner / Investment Committee Compensation: Market-driven deferred salary, performance-linked incentives, and equity participation Search Mandate: Yorktown Search Partners is conducting a confidential executive search on behalf of a growing investment and advisory platform operating across private markets, media, and capital advisory.Role Overview:Yorktown Search Partners has been retained to recruit a Chief Legal Officer / Head of Legal Advisory for a confidential investment platform specializing in principal investing, special situations, media-for-equity, and structured capital solutions. This is a senior-level, partner-track opportunity for a legal executive who thrives at the intersection of law, deal-making, and entrepreneurial execution.As the firms legal architect, you will define and lead legal strategy across mandates, fund vehicles, and partnerships. The role is hands-on and strategic: guiding transactions, ensuring governance best practices, managing external counsel, and building a scalable legal infrastructure. You #39;ll be relied upon to mitigate risk, enhance deal efficiency, and align legal operations with long-term value creation.Compensation includes a market-driven deferred salary, alongside performance-linked incentives and equity participation, ensuring full alignment with the firms growth and capital appreciation.Key Responsibilities:Legal Structuringamp; Transaction Support

• Draft, negotiate, and review all core legal documentation including LOIs, SPAs, subscription agreements, and side letters
• Provide structuring advice for transactions across private equity, co-investments, media-for-equity, and special situations
• Partner with investment and advisory teams to optimize legal and commercial outcomes

Governanceamp; Regulatory Oversight

• Lead entity governance, board documentation, and shareholder communications for platform and portfolio companies
• Maintain firm-wide compliance with securities laws, corporate registrations, and jurisdictional filings
• Oversee firm governance processes including cap table management, resolutions, and investor documentation

External Counselamp; Legal Resource Management

• Manage external counsel relationships across corporate, securities, IP, fund formation, and cross-border matters
• Prioritize legal spend and ensure timely, cost-effective engagement with advisors
• Build internal legal toolkits, playbooks, and workflows that enhance responsiveness and institutional quality

Complianceamp; Risk Management

• Implement and maintain internal compliance policies, including AML/KYC protocols and investor onboarding procedures
• Monitor legal risks across mandates and ensure the platform is diligence-ready for institutional partners and audits
• Serve as a key advisor to the Managing Partner and Investment Committee on regulatory, contractual, and reputational risks

Ideal Candidate Profile:

• 10-15+ years of legal experience in corporate law, M amp;A, securities, or fund advisory (BigLaw, boutique firm, or in-house counsel)
• Demonstrated experience in structuring private investments, fund entities, and complex transactions
• Licensed to practice in a common law jurisdiction (Canada, U.S., or UK preferred)
• Strategic operator with a hands-on approach and high comfort with ambiguity
• Track record of supporting entrepreneurial, high-growth environments or financial services platforms
• Strong business acumen and collaborative mindset

Ideal First Hire:The Chief Legal Officer will be expected to hire a Legal Counsel, Corporateamp; Securities-a fractional or part-time legal professional to support day-to-day drafting, cross-border compliance, and transaction execution. This first hire will help scale the legal function alongside the platforms growth.Compensationamp; Alignment:This is a senior leadership position with a market-driven deferred salary structure, complemented by equity participation and performance-based incentives. Compensation is aligned with the firms entrepreneurial model, rewarding long-term value creation, governance stewardship, and strategic leadership.