Advise emerging companies on Canadian employment and labour matters across hiring, contracts, compensation, terminations, policies, investigations, and tribunal responses. Draft and maintain agreements, handbooks, severance, and restrictive covenants. Identify repeat issues and improve templates and AI-powered workflows; help define legal delivery standards and collaborate with founders and engineering to shape firm processes.
About Us
Blackletter is reinventing legal services from first principles.
We pair frontier automation with top-tier lawyers. This allows our firm to deliver elite legal services with fast turnaround, predictable pricing, and a transformed experience for our clients and for the lawyers doing the work.
Early traction has been strong. We are serving a growing roster of clients across venture financing, commercial, corporate, and employment, and we are backed by leading venture investors.
Our founding team brings experience from frontier AI labs, leading law firms, and some of the top law schools in North America.
The most impactful firm in the world ten years from now will not be one founded in the 1900s, or the 1800s. It was founded in 2026.
We are a small team making our earliest hires, with a significant opportunity to shape not only our company, but the entire legal profession.
The Role
You will work directly with emerging companies to advise on the full range of employment matters that arise as they hire, scale, and restructure their teams. But this is not a traditional counsel role. You will work closely with the founders and technical team to help shape how the firm operates, including the tools, workflows, and standards that make legal work faster and more consistent.
Your expertise does not just serve clients. It educates our platform, making it faster and smarter for the next matter.
What You Will Do
- Draft, review, and advise on employment agreements, offer letters, contractor and consulting arrangements, and separation agreements
- Counsel founders on hiring, worker classification, compensation structures, and the employment terms that accompany equity grants
- Draft and maintain workplace policies and employee handbooks as clients grow
- Guide clients through terminations, layoffs, severance, and releases, including assessing risk and exposure
- Advise on restrictive covenants, confidentiality, and IP assignment in the employment context
- Support clients on workplace investigations, human rights and discrimination issues, and responses to agency or tribunal matters
- Identify patterns across matters and translate them into better templates, clauses, and playbooks
- Provide input on the design of the AI-powered workflows to best serve our clients
- • Help define what excellent legal delivery looks like, from client communication standards to matter management processes
Who We Are Looking For
Experience: 4-10 years at a leading law firm or in-house, with significant experience advising on Canadian employment and labour matters. Licensed to practise in Ontario, or eligible to be. Experience working with high-growth or technology companies is preferred.
Judgment: Strong commercial instincts and the ability to give clear, practical advice in situations that are often time-sensitive and high-stakes.
Orientation: You notice when the same issue comes up repeatedly and look for a way to handle it better the next time. You are frustrated by how long routine legal work takes and are open to changing how it gets done.
Compensation and Structure
Competitive salary plus equity. Compensation is commensurate with experience. This role is based in our Toronto office, with three days per week in-office.
Why Us
You will spend more of your time on negotiating, advising, and making judgment calls, and less on work that should already be automated. As one of our first legal hires, you will have a direct hand in shaping the future practice of law.
If some of the above doesn’t line up perfectly with your experience, we still encourage you to apply!
We value and celebrate diversity and strive to create an inclusive work environment for all. We welcome applicants from all backgrounds and are committed to providing equal opportunities. Should you require any accommodations during the recruitment process, please reach out to [email protected].
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