Chief Legal Officer / Head of Legal Advisory

Yorktown Search Partners; Toronto; Hybrid; CAD 100,000 - 125,000; Full time

Job summary

A growing investment and advisory platform is seeking a Chief Legal Officer / Head of Legal Advisory to oversee legal structuring and governance. The role requires 10-15 years of legal experience, particularly in corporate law and M&A, along with strategic insight and a collaborative mindset. The compensation structure includes a market-driven deferred salary, equity participation, and performance-based incentives, aligning with the firm’s entrepreneurial model.

Qualifications

• 10-15+ years of legal experience in corporate law, M&A, securities, or fund advisory.
• Demonstrated experience in structuring private investments and complex transactions.
• Strong operator mindset and comfort with ambiguity.

Responsibilities

• Draft, negotiate, and review all core legal documentation.
• Lead entity governance and maintain compliance with securities laws.
• Manage relationships with external counsel and implement compliance policies.

Skills

Legal experience in corporate law

M&A and securities

Ability to manage external counsel

Strategic planning and execution

Strong business acumen

Education

Licensed to practice in a common law jurisdiction

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.

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 Structuring & 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

Governance & 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 Counsel & 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

Compliance & 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&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, Corporate & 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.

Compensation & 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.