Associate General Counsel & Privacy Officer (Remote First)

About Us

The company is redefining commercial insurance for Canadian businesses.

As a leading InsurTech, we make getting the right coverage simple, fast, and accessible through a digital-first experience. Our platform combines advanced technology with deep industry expertise to deliver tailored insurance solutions that help businesses thrive.

The company has been recognized for its rapid growth and industry impact:

✅ Deloitte’s Technology Fast 50 (2023, 2024, 2025)

✅ Deloitte’s Technology Fast 500 (2024, 2025)

✅ Top Insurance Employers (2022)

At the company, we value ownership, collaboration, and innovation. Our team thrives on solving complex challenges, challenging the status quo, and making a real impact in an industry ready for change.

If you're looking to build something meaningful in a fast-growing, customer-focused company, we’d love to hear from you!

As we continue to rapidly grow, we are looking for an Associate General Counsel & Privacy Officer to help scale our oversight functions while maintaining our innovative DNA.

Reporting to the General Counsel, you will play a pivotal, dual role. You will have a direct seat at the table to provide high-level legal support across all business units—from Underwriting to IT—while serving as the enterprise’s primary authority and designated Privacy Officer. Alongside the General Counsel, working closely with senior leadership (encompassing the CEO & Founder, COO, and VPs of Sales, Marketing, Technology, People, and Finance), you will safeguard our digital operations, commercial strategies, and technological innovations.  For the right candidate, this role is anticipated to grow as the company continues to scale upwards.

Responsibilities

• Legal Operations & Commercial Oversight

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Contract Lifecycle Management: Draft, review, and negotiate complex commercial agreements, including SaaS licenses, vendor contracts, and partnership/binder agreements with our insurance markets.

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MGA & Underwriting Support: Support product development, underwriting authorities, and digital automation risks.

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Regulatory Compliance & Governance: Ensure ongoing compliance with provincial insurance regulators (such as RIBO) across Canadian operating provinces. Assist the GC in preparing materials for the Board of Directors.

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Claims & Litigation Support: Provide expert legal guidance to the internal Claims/Errors & Omissions (E&O) team on complex files, litigation matters, and risk mitigation strategies.

• Privacy & Data Governance (Designated Privacy Officer)

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Privacy Program Leadership: Serve as the official enterprise authority on privacy, maintaining and evolving our data protection framework alongside the Information Security Officer (ISO) to ensure strict adherence to PIPEDA and provincial legislation.

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Privacy Assessments: Develop, maintain, and oversee Privacy Impact Assessments (PIAs), with a specific focus on protecting an online, digital-first insurance platform.

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Incident Response & Training: Lead the legal response team for data security incidents or privacy inquiries, managing breach notification assessments and transparent reporting. Develop and deliver ongoing compliance and privacy training for our 350+ staff members.

• AI, Technology & Marketing Innovation

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AI Governance & Tech Ethics: Collaborate closely with IT, software engineers, and data scientists to establish ethical and legal guardrails for AI implementation, machine learning initiatives, and AI-driven underwriting tools.

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Compliant Disruption: Stay ahead of emerging Canadian tech regulations to ensure our "speed-to-quote" technology remains a competitive advantage while staying fully compliant.

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Marketing Review: Partner with our high-growth marketing team to review digital, online, and traditional marketing initiatives, ensuring regulatory compliance for the company's largest budget component.

• Compliance & Ethics

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Support the GC/CECO in maintaining and evolving our corporate Ethics and Compliance program, ensuring our culture of integrity evolves with our growth.

Qualifications

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Education & Bar Admission: Bachelor of Laws (LL.B.) or Juris Doctor (J.D.) degree; active member in good standing with a Canadian common law society (e.g., Law Society of Ontario).

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Experience: 6 to 10+ years of post-call legal experience, with substantial in-house experience inside an insurance carrier or brokerage (P&C preferred) as a primary requirement. Blends rigorous foundational training at a top-tier law firm with hands-on domain expertise advising on insurance regulatory compliance, commercial distribution partnerships, policy wordings and coverage forms, and complex claims strategy.

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Industry & Tech Knowledge: Deep familiarity with the Canadian insurance regulatory landscape, digital brokerage models, and MGA structures. Comfort advising on digital technology, online platforms, and advanced tools like AI.

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Privacy Credentials: Demonstrated expertise in data protection law; a professional privacy certification (e.g., CIPP/C) is highly preferred and considered a significant asset.

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The "Startup-to-Scaleup" Mindset: Proven ability to navigate a corporate transition from a "build fast" startup environment to a highly regulated, "steady-state" corporate structure. Ability to formalize corporate governance without stifling innovation.

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Corporate Diplomacy & Influence: Exceptional communication skills with the ability to translate complex legal risks into solution-oriented business advice for non-legal stakeholders. Possess the "corporate diplomacy" required to speak the entrepreneurial language of a tech startup while satisfying the rigorous reporting demands of a Fortune 500 parent company.

Why the company?

The Best of Both Worlds: Experience the entrepreneurial spirit and speed of a tech disruptor combined with the stability, backing, and resources of a global insurance giant.

Direct Impact: As the second lawyer in the organization, your work will directly shape our corporate processes, legal frameworks, and scaling trajectory.

At the Forefront of Innovation: We don't just use tech; we build it. You will face cutting-edge legal issues involving AI and digital automation in the evolving Insurtech space.

Benefits & Perks at the company

At the company, we know that when our people thrive, so does our business. That’s why we offer a flexible, people-first work environment designed to support your well-being, growth, and success.

💻 Work Your Way

• Remote-first setup for added flexibility
• Home office allowance to create a comfortable workspace
• Top-tier tech: "Office in a box" with all necessary tech equipment
• Half days before public holidays: Enjoy half days before long weekends

❤️ Your Health, Your Way

• Flexible health and dental plans for families, including mental health support
• Health & personal spending accounts to invest in wellness your way
• Parental leave top-up, because family comes first

🚀 Investing in Your Growth

• Education assistance reimbursement for courses, conferences, books, and memberships
• Opportunities to learn from industry experts and grow your career

🤝 Staying Connected

• Weekly Friday huddles to share updates and connect across teams
• Virtual & in-person team-building events to strengthen our culture

We’re building something special. Come be a part of it!

AI Tools and Your Interview

We know AI is a valuable tool, and you're welcome to use it to prepare for your interview. However, please don't use AI assistants during the live interview itself. We want to have an authentic conversation with you, and using AI during the interview could affect our evaluation of your suitability for the role.

Just so you know, we use an AI scribe to help us take notes and review interviews, ensuring a fair and clear process.

Diversity & Inclusion

The company celebrates diversity and is committed to creating an inclusive environment. We welcome applications from all backgrounds and provide accommodations throughout the hiring process. If you need support, let us know, we’re here to help.