Managing Counsel, Product (Payroll experience required) in Canada Creek, Nova Scotia at Jobgether

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Managing Counsel, Product (Payroll experience required) based in Canada.

This is an individual-contributor legal leadership role supporting the development of complex HR technology products across global markets.
You’ll act as a strategic legal partner to Product, Payroll, Engineering, Privacy, Security, and Commercial teams.
The role has a particular focus on payroll, AI/ML, data protection, employment law, and emerging technology regulation.
You’ll translate complex legal requirements across 90+ jurisdictions into practical guidance and actionable product requirements.
The position combines deep legal expertise with commercial judgment, product thinking, and a strong interest in technology and AI.
You’ll work in a highly distributed, asynchronous environment alongside an experienced international legal team.
The opportunity is well suited to a pragmatic lawyer who enjoys solving complex problems and enabling innovation while managing regulatory risk.

• Provide end-to-end product legal counsel for payroll and AI-enabled products, including launch-readiness assessments, AI impact assessments, model cards, governance frameworks, and risk controls.
• Partner closely with Product, Engineering, Payroll, Privacy, Security, and Commercial Legal teams to identify and address legal considerations throughout the product lifecycle.
• Advise on product terms and conditions and AI-specific contractual provisions, including data and metadata use, training, output and intellectual property ownership, acceptable use, and transparency requirements.
• Monitor emerging AI, technology, employment, data protection, and payroll regulations across multiple jurisdictions and translate developments into clear, actionable requirements for product, design, and engineering teams.
• Support compliance with frameworks such as the EU AI Act, UK AI regulatory approaches, US federal and state developments, Canadian AI legislation, GDPR, and CCPA.
• Partner with Privacy and Security teams on DPIAs, TIAs, incident response, vendor assessments, and diligence relating to AI/LLM providers.
• Manage external counsel on complex, multi-jurisdictional matters, ensuring advice is practical, commercially focused, and aligned with business objectives.
• Deliver targeted legal enablement through training sessions, office hours, and practical guidance for internal stakeholders.
• Identify pragmatic solutions to complex legal and regulatory challenges rather than simply escalating issues.
• Contribute to the development of legal and governance frameworks that enable the responsible launch and scaling of technology products.

• Qualified lawyer with substantial experience advising on technology products, preferably across multiple jurisdictions or legal systems.
• Proven product counsel experience within technology, with strong expertise in HR technology, payroll, PEO, EOR, HRIS, or related employment technology platforms.
• Demonstrated ability to advise on complex products at scale and work across multiple jurisdictions.
• Deep knowledge of AI/ML legal and regulatory frameworks, including the EU AI Act, UK AI regulatory developments, US federal and state approaches, and Canadian AI legislation.
• Strong understanding of the intersection between AI regulation, data protection, employment law, and payroll compliance.
• Significant experience with payroll compliance is required, ideally across multiple jurisdictions.
• In-house legal experience is preferred, particularly within a technology company or fast-growing environment.
• Experience working in a startup or similarly fast-paced organization is an advantage.
• Strong analytical, organizational, and problem-solving abilities, with a practical and commercially minded approach to legal advice.
• Excellent written and verbal English communication skills, with the ability to translate complex legal concepts into clear guidance for technical and non-technical stakeholders.
• Strong interest in technology, HR technology, AI, and emerging digital products.
• Comfortable using modern collaboration and productivity tools such as Slack, Notion, Google Drive, Claude, or equivalent technologies.
• Experience working remotely and asynchronously is an advantage.

• Annual salary range of USD $66,300–$186,400, with actual compensation determined by location, experience, skills, training, business needs, and market conditions.
• Globally distributed, work-from-anywhere environment.
• Flexible working hours within an asynchronous operating model.
• Flexible paid time off.
• 16 weeks of paid parental leave.
• Budget for coworking spaces, learning, wellness, and related professional or personal development activities.
• Mental health support services.
• Stock options.
• Home office budget and IT equipment.
• Compensation philosophy focused on pay equity, competitive local market rates, and fair compensation across global locations.
• Opportunities for professional growth, internal mobility, and exposure to complex international HR-tech and AI legal matters.
• Inclusive, globally distributed working environment with employee resource groups and support for workplace accommodations.