Senior Legal Counsel
Shakepay is a Canadian platform designed for buying and selling Bitcoin and Ethereum. It aims to make cryptocurrency accessible to Canadians, offering commission-free transactions, rewards programs like ShakingSats for free bitcoin, and a Shakepay Card for earning bitcoin cashback. The service is regulated and focuses on security and user control over their digital assets.
About Shakepay
Shakepay is a Canadian platform that allows users to buy, sell, and earn cryptocurrencies like Bitcoin and Ethereum. The service emphasizes ease of use, enabling users to set up an account and begin transactions within minutes. Key features include commission-free trading at market-leading prices, the ability to earn bitcoin rewards through various activities such as shaking the phone (ShakingSats), cashback on purchases with the Shakepay Card, and a referral program. The platform supports direct deposits and allows users to move their digital assets to a private wallet or cash out to a bank account quickly. Shakepay highlights its security measures, including keeping digital currencies in secure, offline storage backed by insurance. The company is regulated as a member of the Canadian Investment Regulatory Organization (CIRO), registered as an Investment Dealer in all Canadian provinces and territories, and licensed as a Money Service Business by FINTRAC.
Skills
About the Role
You'll help shape how millions of Canadians interact with money, working 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 where you'll navigate ambiguity, provide practical recommendations, and help build the business rather than just protect it. You'll partner across teams to design and launch new products, advise on a wide range of legal and regulatory matters, and support regulatory engagement including examinations, audits, and licensing. You'll also have the opportunity to identify ways to use AI and automation to make legal work more efficient and scalable.
Requirements
- 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, starting from the product or business outcome to help the team understand risk, options, and a recommended path
- Comfortable advising product and operational teams directly, including on ambiguous questions
- Strong written and verbal communication skills, able to turn complex legal issues into clear, practical guidance for non-legal stakeholders
- Experience working across both a law firm and an in-house legal team
- Experience in a startup or scaleup environment where priorities change quickly
- 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
Responsibilities
- 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 the 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
- Identify opportunities to leverage AI, automation and scalable processes to improve how legal work gets done
- Support the team on other legal matters as needed, including commercial agreements, corporate governance, employment and strategic projects
Benefits
- Stock options for every employee
- Continuous feedback and quarterly performance and compensation review
- Health and dental coverage, including health and wellness spending accounts
- Remote-friendly work from anywhere in Canada, with optional access to office spaces in Montreal and Toronto
- $2,000 annual budget for courses, certifications, and training
- 20 days of vacation per year, plus a $1,000 bonus if all vacation is used
- Parental leave top up to 100% of salary for 18 weeks
- Quarterly team-specific or company-wide offsite