About the team

The Legal team sits at the center of some of Shakepay's most important decisions. We partner closely with Product, Compliance, Operations, Finance, People, and leadership to bring new products to market, navigate complex regulatory questions and help the business move quickly with confidence. We believe ownership over hierarchy, practical judgment over perfection, and using technology and AI to rethink how legal work gets done.
About the role

As Senior Legal Counsel, you'll help share how millions of Canadians interact with money. You'll work alongside product, compliance and executive leadership to solve novel legal questions at the intersection of crypto, payments and financial regulation. This is a hands-on role for someone who can navigate ambiguity, provide practical recommendations and wants to help build - not just protect - the business.
What you'll be doing

• Partner with Product, Compliance and business teams to help design and launch new products, translating complex legal and regulatory requirements into practical solutions.
• Advise on a broad range of legal and regulatory matters across securities, AML/ATF, payments, consumer protection and other areas impacting Shakepay's business.
• Lead regulatory initiatives, including supporting examinations, audits, licensing work, policy development and engagement with regulators.
• Provide practical, business-oriented advice to leaders across the company, helping teams navigate ambiguity and make informed decisions while balancing legal, regulatory and operational considerations.
• Identify opportunities to leverage AI, automation and scalable processes to improve how legal work gets done and enable the business to move faster.
• Support the team on a variety of other legal matters as needed, including commercial agreements, corporate governance, employment and strategic projects.

Who we're looking for

• Canadian-qualified lawyer with 5+ years of experience, ideally in fintech, payments, financial services, crypto, or a fast-moving technology company.
• Able to operate independently in a lean team, make decisions with incomplete information, and move work forward without heavy oversight.
• Business-oriented legal judgment: you start from the product or business outcome, then help the team understand risk, options, and a recommended path.
• Comfortable advising product and operational teams directly, including on ambiguous questions where there may not be a perfect answer.
• Strong written and verbal communication skills, with the ability to turn complex legal issues into clear, practical guidance for non-legal stakeholders.

Bonus points

• Experience working across both a law firm and an in-house legal team.
• Experience in a startup or scaleup environment where priorities change quickly and legal support needs to be pragmatic.
• Familiarity with Bitcoin, crypto, securities, payments, AML, or regulated financial products in Canada.
• Experience using AI, automation, or lightweight tooling to improve legal work product and team efficiency.

Why join us?

• Help shape the future of money: Be part of a team that's revolutionizing financial services in Canada, one sat at a time.
• Impact millions: As cryptocurrency continues to gain traction, our potential for growth is massive. You can help us bring Shakepay and Bitcoin to all Canadians.
• Grow your career: We're growing, and so can you! We have programs in place to encourage continuous learning, growth, and development.
• Ideas, not titles: We want the best ideas to make their way through, no matter where they come from.

Perks and benefits

• Be an owner: Every employee has stock options as part of their total compensation.
• Reach your goals: Develop with continuous feedback and quarterly performance and compensation review.
• Health & wellness: Access to health and dental coverage, including health and wellness spending accounts.
• Remote-friendly: Work from anywhere in Canada, with optional access to our office spaces in Montreal and Toronto.
• Level Up: A $2,000 annual budget for courses, certifications, and training to support your career growth.
• Time off: 20 days of vacation per year. And if you use all your vacation, we give you a $1,000 bonus.
• Parental leave: Enjoy a parental leave top up to 100% of your salary for 18 weeks.
• Have fun together: quarterly team-specific or company-wide offsite to connect with each other.

The base salary range for this position is 150,000 - 220,000 CAD. Base pay may vary based on factors such as years of experience, skills and qualifications. Additionally, employees are eligible for equity, pay increases based on performance, benefits including health and dental care, and paid time off.

We understand that potential can be just as valuable as experience. If you're eager to learn, grow, and contribute to the mission but worry that you may not have the "right" experience, we still want you to apply. We encourage applications from everyone, regardless of background and life experience. We're firm believers that a little bit of slope makes up for a lot of y-intercept.

We use technology, including artificial intelligence (AI), to support certain parts of our hiring process. This can include tools that assist with scheduling, application review, candidate communications, and generating interview notes, guides, or summaries so our team can stay focused on the conversation. All hiring decisions are made by our hiring team.

Fluency in English is required due to the percentage of English-speaking customers and the nature of our platform, which is available to all Canadians.