We are looking for a Contracts and Compliance Specialist to join our legal team, reporting directly to the General Counsel. This role combines substantive legal work with operational ownership across contract management, compliance operations, insurance coordination, and policy development. The Specialist will lead day-to-day legal operations, own their work product, and collaborate with the General Counsel on higher-complexity matters.

Responsibilities
Contract Review and Negotiation

Review, redline, and negotiate NDAs and other low-to-moderate-risk commercial contracts, escalating higher-risk issues to the General Counsel with explicit analysis and recommended positions

Maintain and improve contract templates, playbooks, and clause libraries

Track contract status and deadlines, ensuring timely execution and renewal

Client Compliance and Vendor Management

Serve as the primary point of contact for client procurement compliance requirements, including vendor onboarding questionnaires, recertifications, and audit requests

Develop and maintain response templates and internal policies that enable efficient responses to compliance requests

Design repeatable processes for triaging, tracking, and completing compliance requests within required timelines

Support corporate compliance initiatives, including regulatory monitoring and policy implementation, in partnership with the General Counsel

Insurance Coordination

Review insurance requirements in client contracts and confirm appropriate coverage types and limits





Coordinate with brokers to obtain and distribute certificates of insurance and policy endorsements as required by client agreements

Flag coverage gaps or unusual requirements for General Counsel review

Policy Development and Legal Operations

Draft, revise, and maintain internal policies across areas such as data privacy, information security, acceptable use, and workplace conduct for General Counsel review

Collaborate with cross-functional stakeholders to ensure policies are practical and enforceable

Support other legal operations initiatives and special projects as needed

Additional Responsibilities (As Needed)

Provide litigation support, including coordinating document holds, gathering responsive materials, and liaising with outside counsel under General Counsel direction

Required Qualifications

Bachelor's degree required; paralegal certificate, J.D., or other legal education strongly valued

3 to 7 years of experience in legal operations, contracts management, compliance, or a comparable paralegal role

Demonstrated experience reviewing and negotiating commercial contracts, including NDAs and vendor agreements

Working knowledge of compliance frameworks, vendor management programs,



and client procurement processes

Experience drafting or maintaining internal policies and procedures

Proficiency with contract management tools, document management systems, and Microsoft Office

Preferred Qualifications

Paralegal certification (CP, ACP, or RP) or equivalent credential

Experience in a legal department at a professional services, technology, or consulting firm

Familiarity with privacy regulations (GDPR, CCPA/CPRA)

Experience building or improving legal operations workflows

Exposure to CLM platforms or AI-assisted legal tools

Familiarity with insurance certificate workflows and common coverage types (general liability, E&O;, cyber)

Attention to Detail : Produces accurate, thorough work product across contracts, compliance submissions, and policy documents

Problem-Solving : Evaluates options and proposes practical solutions rather than simply flagging problems

Independent Judgment : Works autonomously, manages competing priorities, and recognizes when to elevate

Communication : Writes clearly for legal and business audiences; communicates professionally with clients, brokers, and internal stakeholders

Adaptability : Embraces variety and takes on new challenges, from learning a compliance framework to building a process from scratch

Reporting and Work Arrangement
Reports directly to the General Counsel. Ability to work fully from the office in Downtown Toronto is preferred, but we are also open to remote.

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📌 Contracts and Compliance Specialist (Ontario)
🏢 Trindent Consulting
📍 Ontario