Senior Legal Counsel Technology & Commercial

CAA Club Group; Vaughan; On-site; CAD 140,000 - 190,000; Full time

Job summary

CAA Club Group is seeking a Senior Legal Counsel to partner with the Information Technology division on enterprise-scale digital transformation initiatives. You will draft, negotiate and advise on SaaS, cloud, software license and related technology agreements, ensuring legal risk is managed across procurement, implementation and transition.

Ideal candidate has 6+ years post-call experience, a J.D./LL.B. from a recognized school and Ontario licensure, with strong understanding of cloud/SaaS

Qualifications

• J.D./LL.B. degree from a recognized law school.
• Licensed and in good standing with the Law Society of Ontario.
• At least six (6) years of relevant post-call legal experience in private practice, an in-house legal department, or a combination of both.
• Substantial experience reviewing, drafting and negotiating complex technology and commercial agreements, ideally in support of a sophisticated IT function.

Responsibilities

• Provide high-quality, timely, solution-oriented corporate-commercial legal advice in support of CCG’s business.
• Review, draft and negotiate technology and commercial agreements including SaaS, cloud-service, software licenses and related arrangements.
• Advise on legal and commercial issues across the technology contracting lifecycle; support procurement, renewal, expansion, and transition.

Skills

Legal drafting

Technology contracts

Commercial agreements

Contract negotiation

Cloud/SaaS knowledge

Education

J.D./LL.B. degree

Ontario Law Society license

Job description

Career Opportunities: Senior Legal Counsel, Technology & Commercial (8727)

Requisition ID8727-Posted11/02/2026-Legal Advisory & Compliance-Executive Admin-THORNHILL-Corporate-CAA Club Group-Mid-Career-0 - 10%-Full Time- Job Location (country) (1) - Job Location (region) (1)

At CAA Club Group, we are passionate about keeping our Members safe - whether they are on the road, at home, or travelling abroad. As a trusted Member-based organization, we provide products and services that are essential to Members’ safety and peace of mind. With over 2.6 million Members across Ontario and Manitoba, we advocate on issues such as road safety and infrastructure, the environment, seniors’ mobility, and consumer protection. Behind our Member experience is a sophisticated, innovation-driven technology organization that is modernizing our platforms through cloud adoption, data and analytics, digital channels and emerging technologies.

Associates share in each other’s successes, drive change and support each other while cultivating a great working environment to deliver on what is best for our Members. CAA Club Group is part of the CAA Club Group of companies, including CAA Insurance Company and Echelon Insurance.

Who we are

Are you ready to join an award-winning, purpose-driven culture? Welcome to the CAA Club Group of Companies (CCG), where purpose leads to passion!
At CCG, we are committed to delivering an exceptional Associate experience. We offer:

• Work-life harmony with access to an award-winning holistic wellness program
• Continuous learning through our robust corporate curriculum and education reimbursement program
• Incredible rewards, travel incentives, and product and service discounts
• Pay-for-performance and best-in-class recognition programs, and
• Competitive benefits that include a defined contribution plan, personal spending account, and so much more.

Join our growing team where everyone belongs!

What You Will Do

Reporting into the AVP Legal, you will be a legal partner to our Information Technology division, a forward-thinking team leading complex, enterprise-scale digital transformation initiatives. You will:

• Provide high quality, timely and solution-oriented operational and strategic corporate-commercial legal and regulatory analysis, advice, and guidance in support of all facets of CCG’s business, in alignment with company’s established appetite for legal and compliance risk.
• Review, draft and negotiate a variety of technology and commercial agreements including:
  • SaaS, cloud-service and software-subscription agreements;
  • software development, implementation, configuration and integration agreements;
  • software, data, content and intellectual-property licences.
• Advise on legal and commercial issues arising throughout the technology contracting lifecycle, including procurement, implementation, renewal, expansion, suspension, termination and transition, in support of CCG’s strategic technology roadmap and large-scale digital transformation programs.
• Cultivate and maintain effective and collaborative working relationships with key business unit stakeholders.
• Translate complex legal, technical and commercial issues into clear, practical recommendations for business leaders and project teams.
• Work collaboratively with Privacy, Information Security, Enterprise Risk Management, Third-Party Risk Management, and Compliance to identify and address legal and contractual risks.
• Develop and maintain key agreement templates, playbooks, clauses and other key documents (in collaboration with Contract Manager and other Legal Counsel).
• Build a collaborative and productive relationship across the enterprise and with key external stakeholders.
• Support performance management and goal setting for other lawyers and legal professionals (e.g. law clerk, contract manager) within the Legal department.

Please note, salary range is not inclusive of total compensation. The expected salary range for this position will be impacted by factors such as the successful candidate’s skills, experience and working location, as well as the specific position’s business line, scope and level. Candidates with salary expectations outside of the range are encouraged to apply.

Who You Are

• J.D. or LL.B. degree from a recognized law school.
• Licensed and in good standing with the Law Society of Ontario.
• At least six (6) years of relevant post-call legal experience in private practice, an in-house legal department, or a combination of both.
• Substantial experience reviewing, drafting and negotiating complex technology and commercial agreements, ideally in support of a sophisticated, enterprise-scale IT function.
• Strong understanding of modern technology architectures and delivery models (e.g., cloud, SaaS, APIs, agile development) and genuine curiosity about emerging technologies and their legal implications.

Please note that we may use AI tools to help us through the recruitment process.

Our Commitment

We are an equal opportunity employer and are committed to providing employment accommodation in accordance with all applicable Provincial Human Rights and Accessibility Legislation. CCG will provide accommodations to job applicants with disabilities throughout the recruitment process. If you require an accommodation, please notify us and we will work with you to meet your needs.