Senior Legal Counsel

About Shakepay

Since 2015 we have been on a mission to help Canadians build long‑term wealth through bitcoin. Over the past few years we have expanded beyond buying and selling bitcoin to offer a growing suite of everyday financial products—including the Shakepay Card, direct deposit, bill payments and Interac e‑Transfer—making it easier to earn, save and use bitcoin every day. Today, more than 1.5 million Canadians use Shakepay to grow their bitcoin savings and take control of their financial future as we continue to push the boundaries of what modern financial services can look like.

We are regulated as an investment dealer across all Canadian provinces and territories, and backed by renowned venture capitalists with funding of $44M. We have a passionate, loyal, and growing community, and we are looking for people who want to help us build something truly special.

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.

As Senior Legal Counsel, you will help share how millions of Canadians interact with money. You will 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.

• Partner with Product, Compliance and business teams to 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.

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 scale‑up 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.

Help shape the future of money:
Be part of a team that is revolutionizing financial services in Canada, one seat 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 are 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.

• Be an owner:
  Every employee has stock options as part of their total compensation.
• Reach your goals:
  Develop with continuous feedback.