Remote Senior Legal Counsel

About the Role

Hi, I'm Diana, General Counsel at Jane, where I'm lucky to work with smart and empathetic people who care deeply about helping the helpers - the healthcare community who help all of us. This team is all about fostering growth and spreading delight, and as an added plus, Jane is a remote-first company, meaning every role at Jane, including this one, is remote, giving you the freedom to work from any corner of Canada.

We're looking for an experienced lawyer to join us as Senior Counsel, taking a hands-on approach to legal work at Jane, where we believe legal done right can delight. You'll join the small and mighty Legal team, alongside Jane's General Counsel and Senior Legal & Operations Specialist. You'll work closely with leaders and teams across Jane, including our Product, Partnerships, People, Marketing, and Finance teams. You'll advise on a wide range of legal issues, including commercial contracts, healthcare and privacy regulation, litigation risk, employment law, and corporate governance. There's no expectation you'll come in the door with expertise in all of these areas, but you should have high confidence in a good number of them, along with the willingness and ability to build expertise in the rest.

This role will engage your ability to solve complex problems while working with a collaborative team across Jane in a fast-paced environment. The right person for this role understands people, is smart, creative, and detail-oriented, but also highly practical; someone who can balance risk and get things done.

What Impact We’re Looking for You to Make

• Provide knowledgeable, practical, helpful legal advice in a fast-paced environment operating globally (including across Canada, the U.S., and the U.K.), enabling Jane to improve our customers' experience, shorten review timelines, and ship faster and better.

• Identify legal solutions as well as risks — take ownership and identify paths for the team to succeed.

• Review, negotiate, and advise on commercial agreements (MSAs, partnership agreements, vendor terms, NDAs, BAAs, and more), and advise on employment law, litigation risk, and strategy — including drafting and updating templates as our needs evolve.

• Handle law enforcement and regulatory requests (subpoenas, warrants, regulatory inquiries), and advise on IP protection and brand enforcement.

• Build collaborative relationships across Jane, working hand-in-hand with developers, product owners, and others to build products and experiences that delight.

• Communicate clearly and confidently, explaining legal impact in practical, real-world terms that matter to other Janers.

• Help build and scale Legal's AI environment — from automated intake to contract review and document management — so the team can grow without slowing down.

• Mentor others on the team and across Jane, supporting their development and understanding of the law.

What Experience We Need

• 7+ years as a practicing lawyer, including in-house experience advising high-growth technology companies.

• Called to the bar in Canada (Ontario or BC preferred); US bar admission is an asset. Other global bar admissions and experience are also valued and welcomed.

• Established expertise in at least 3 of the following areas, with the ability and commitment to strengthen expertise in the others: commercial contracts, privacy regulation, healthcare regulation, litigation risk, employment law, and corporate governance.

• Proactive problem-solver with excellent communication skills, comfortable working with cross-functional teams and able to explain complicated things simply and clearly.

• A true advisor who builds strong relationships and communicates effectively, making an impact on outcomes.

• Thrives in a fast-paced environment and can prioritize across multiple tasks.

• Demonstrates ethical integrity and the ability to manage confidential information with discretion.

• Comfortable using AI and technology in your legal work, including in contract revi