About the Role 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 clear 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 qualified 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)
Key Competencies 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
📍 Ontario