Head of Legal, Risk & Compliance

Lockton; Toronto; On-site; CAD 180,000 - 260,000; Full time

Job summary

Lockton in Canada seeks a Head of Legal, Risk & Compliance to serve as the senior legal and compliance leader for Canadian operations. The role provides practical, commercially focused advice to leadership and business teams while guiding regulatory compliance, privacy, and contract risk in a complex insurance brokerage environment.

The successful candidate will operate at strategic and hands-on levels, negotiating sophisticated agreements and partnering with senior executives to balance legal

Qualifications

• Law degree from a recognised Canadian or equivalent law school.
• Member in good standing of a Canadian provincial or territorial law society, or eligible to become a member.
• 10+ years of relevant legal experience, preferably with in-house, compliance, privacy and commercial exposure.

Responsibilities

• Serve as the senior legal resource for the Canadian business and provide practical guidance to senior leadership and stakeholders.
• Advise on legal and regulatory issues affecting the Canadian insurance brokerage business.
• Identify and help manage legal and regulatory risks across activities and relationships.
• Translate complex legal requirements into pragmatic business guidance.

Skills

Legal leadership

Regulatory compliance

Privacy expertise

Contract negotiation

Stakeholder management

Education

Law degree (Canadian or equivalent)

Bar admission / member in good standing

Job description

The Head of Legal, Risk & Compliance, Canada will serve as the senior legal and compliance leader supporting the organisation's Canadian operations. This individual will provide practical, commercially focused legal advice to Canadian leadership and business teams, while leading and supporting matters relating to regulatory compliance, privacy, commercial contracting and legal risk.

This role requires an experienced Canadian lawyer who can operate effectively at both the strategic and hands‑on levels. The successful candidate will be comfortable working directly with senior business leaders, reviewing and negotiating commercial arrangements, interpreting regulatory requirements and developing practical approaches to managing legal and compliance risk within a complex insurance brokerage environment.

Key Responsibilities

Legal Leadership & Strategic Advice

• Serve as the senior legal resource for the Canadian business and provide practical legal guidance to senior leadership and business stakeholders.
• Advise on legal and regulatory issues affecting the Canadian insurance brokerage business.
• Identify, assess and help manage legal and regulatory risks associated with business activities, strategic initiatives and commercial relationships.
• Translate complex legal and regulatory requirements into pragmatic business guidance.
• Partner closely with Canadian leadership and the broader Legal, Risk and Compliance organisation.

Compliance & Regulatory Risk

• Provide leadership and guidance on compliance matters affecting Canadian operations.
• Advise business leaders on regulatory obligations and emerging compliance risks.
• Support the development, implementation and ongoing enhancement of Canadian compliance policies, controls and programmes.
• Assist business teams in identifying, escalating and addressing potential compliance issues.
• Partner with broader compliance resources to promote a strong culture of integrity, accountability and regulatory awareness.
• Support regulatory reviews, inquiries and related compliance matters where appropriate.

Privacy & Data Protection

• Provide legal guidance on Canadian privacy and data‑protection requirements.
• Advise business teams on the collection, use, disclosure and protection of personal and confidential information.
• Partner with internal stakeholders on privacy‑related policies, practices, contractual requirements and risk management.
• Support the organisation in assessing and responding to privacy‑related legal and compliance issues.
• Monitor relevant developments in Canadian privacy requirements and advise the organisation on their potential implications.

Commercial Contracts

• Draft, review and negotiate a broad range of commercial agreements.
• Provide legal guidance on client service agreements and other client‑facing contractual arrangements.
• Advise business stakeholders on contractual risk and support negotiations with clients and other third parties.
• Develop pragmatic solutions that appropriately balance legal protection, regulatory requirements and commercial objectives.
• Help establish consistent contracting practices and support business teams in understanding contractual obligations.

Business Partnership & Stakeholder Management

• Establish strong working relationships with Canadian business leaders and serve as a trusted legal and compliance adviser.
• Work collaboratively with colleagues across Legal, Compliance, Privacy, Risk and other corporate functions.
• Support senior leadership in evaluating legal and regulatory considerations associated with business decisions.
• Provide clear and practical advice that enables the business to move forward while appropriately managing risk.
• Collaborate across Canadian and broader organisational teams on matters spanning multiple jurisdictions or functions.

Qualifications & Experience

Required

• Law degree from a recognised Canadian or equivalent law school.
• Member in good standing of a Canadian provincial or territorial law society, or eligible to become a member.
• 10+ years of relevant legal experience, preferably combining in‑house legal, compliance, privacy and commercial experience.
• Significant experience advising businesses on regulatory compliance and legal risk.
• Strong knowledge and practical experience in Canadian privacy and data‑protection matters.
• Demonstrated commercial contracting experience, including drafting and negotiating sophisticated business agreements.
• Ability to provide pragmatic legal advice within a fast‑moving commercial organisation.
• Strong judgement, analytical and problem‑solving capabilities.
• Excellent written and verbal communication, negotiation and stakeholder‑management skills.
• Ability to engage credibly with senior executives while remaining comfortable handling detailed legal and compliance matters directly.

Preferred

• Experience working in‑house within a commercial insurance brokerage or carrier.
• Strong understanding of the Canadian insurance industry and the regulatory environment in which brokers operate.
• Experience advising a geographically dispersed or multinational organisation.
• Experience working collaboratively with US or global Legal and Compliance teams.

Artificial Intelligence (AI) tools may be used in the process to screen, assess, or select applicants for a position but all final decisions and determinations are made exclusively by authorized human personnel.

This job posting is an advertisement for an existing vacancy.

Lockton Companies is an equal opportunity employer.