Rate: $160-185k base max – 32% bonus – 30% equity – 4 weeks’ vacation + 6 additional days.

Hybrid: 5 days a week - Mississauga

Must Haves

7-10+ years of corporate/commercial legal experience, including at least 5-7 years supporting a business in an in-house counsel capacity.

JD/LLB and membership in good standing with a Canadian law society.

Strong experience supporting ecommerce, digital commerce, or technology-driven businesses.

Deep knowledge of advertising law, privacy law, consumer protection, and data governance.

Experience advising on ad-tech platforms, digital advertising ecosystems, media buying and selling, and DSP (Demand‑Side Platform) environments.

Proven ability to draft, negotiate, and manage complex commercial agreements, strategic partnerships, and technology-related contracts.

Experience partnering closely with sales and commercial teams, providing practical legal guidance that supports revenue growth while mitigating risk.

Strong understanding of customer data usage, audience targeting, analytics, campaign measurement, and privacy compliance.

Experience drafting and negotiating advertising terms and conditions with clients, agencies, vendors, and strategic partners.

Ability to review marketing, advertising, and sales materials and advise on what claims, customer information, and performance data can be legally disclosed.

Strong business acumen with the ability to balance legal risk against business objectives in a fast‑paced setting.

Plusses

Experience supporting a retail media network or enterprise retail organization.

Previous experience advising media, advertising technology, marketing technology,



or digital media companies.

Experience supporting omnichannel advertising programs across digital, ecommerce, mobile, and physical retail environments.

Familiarity with emerging regulations and industry trends related to artificial intelligence, digital advertising, consumer data, and online marketplaces.

Experience building governance frameworks, compliance programs, and scalable legal processes for advertising and data use.

Experience managing external counsel and specialized legal advisors.

Exposure to product development and technology teams, particularly within data‑driven advertising environments.

Day-to-Day Responsibilities

Serve as a strategic legal advisor to the enterprise retail media and advertising business, partnering with commercial, sales, product, marketing, and technology stakeholders.

Provide legal guidance on the development, launch, and scaling of advertising products, retail media solutions, and customer engagement initiatives.

Draft, review, negotiate, and structure commercial agreements involving advertisers, agencies, media platforms, technology providers, ad‑tech vendors, and strategic partners.

Support sales teams by reviewing proposals, customer‑facing materials, campaign performance reporting,



and commercial terms to ensure regulatory compliance and minimize legal risk.

Advise on privacy, customer data usage, audience targeting, analytics, measurement capabilities, and data‑sharing practices.

Review marketing campaigns, sponsored content, advertising claims, and customer communications to ensure compliance with applicable legal and regulatory requirements.

Provide guidance on what customer, campaign, and sales performance information can be shared externally during sales pitches and business development activities.

Partner with compliance, privacy, and technology teams to identify legal risks and develop practical solutions that enable innovation and business growth.

Develop and maintain terms and conditions, governance frameworks, and compliance processes related to advertising, data use, and media publishing activities.

Monitor emerging legal, regulatory, and industry developments across privacy, advertising technology, ecommerce, digital media, and artificial intelligence, translating those developments into actionable business recommendations.

Collaborate cross‑functionally with internal stakeholders and external counsel to address complex legal matters and support strategic business initiatives.

This profile would be ideal for someone coming from a retail media, ecommerce, ad‑tech, digital advertising, media agency, or enterprise retail workplace who has experience acting as a business‑oriented legal partner to sales and commercial teams.

Vacant opening / net new role

AI may be used to generate o r format the

📌 Commercial Lawyer (E-Commerce Technology) (Winnipeg)
🏢 Insight Global
📍 Winnipeg