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Toronto, Ontario, Canada
Hybrid
Legora is redefining how legal work gets done. Not built for lawyers, built with them. We work alongside the world’s best legal teams, who expect excellence, precision, and speed, and we hold ourselves to the same bar.
Our AI-native workspace lets legal professionals move faster, think more clearly, and operate with sharper precision. By analysing thousands of documents in minutes and powering end-to-end workflows, we cut through complexity, teams can focus on what matters: judgment, strategy, and outcomes.
2,100+ customers across 80+ countries trust us, including Cleary Gottlieb, Goodwin, Linklaters, White & Case, Dentons, and Barclays. We’ve scaled to $200M+ in ARR, with teams across Europe, North America and APAC, and continue to expand through acquisitions including Qura, Walter AI, Graceview, Cadastral, and Wexler.
We partner with world-class performers: including Aaron Judge and the New York Yankees, Ludvig Åberg (and his caddie), and campaigns featuring Jude Law.
Joining Legora means three things.
We lean in: ownership over titles, outcomes over intentions.
We fight for excellence: high standards, direct, ego-free feedback.
We grow together: as a team and with our customers.
Mission before ego. Everyone contributes. No one coasts.
If you’re driven by impact, pace, and raising the bar. This is the place.
Let's get the tricky part out of the way. Legal Engineering does not fit neatly into a traditional box. It combines legal practice, product fluency, enterprise change, commercial judgment and client leadership.
As Director, Legal Engineering, your mission is to make Legal Engineering the commercial and delivery engine for Canada, anchored in our Toronto office. Reporting to the Head of Legal Engineering, North America, you will set the craft bar, build the Canadian team and its Team Lead layer, partner closely with Go-to-Market and Engagement, lead selectively on the highest-stakes clients, and turn local learning into playbooks that scale across the Canadian market.
This is a Director-level leadership role. Your primary output will be the quality and performance of the team and system you build. You will stay close enough to the product and the work to coach credibly, while moving your own time toward hiring, leadership development, senior relationships, market strategy and cross-functional execution.
You will have the autonomy to shape how Legal Engineering runs in a strategically important market, together with the responsibility to keep that model connected to Legora's North American and global standards.
Lead the Legal Engineering function for Canada from the Toronto office, including its operating rhythm, quality bar, capacity model and local partnership with Go-to-Market and Engagement.
Hire exceptional Legal Engineers and future leaders. Own the quality bar from sourcing and interview calibration through closing, onboarding and ramp.
Build a manager layer of Team Leads who each own and develop a group of Legal Engineers. Delegate real decision rights and create clear succession paths so the function becomes stronger and less dependent on you over time.
Give direct, evidence-based feedback. Coach hard, set clear expectations and act decisively when the performance or values bar is not met.
Partner with Canadian commercial leadership on priority accounts, pilots, rollouts and escalations. Connect Legal Engineering activity to conversion, adoption, usage, expansion and revenue.
Act as the lead legal architect on selected enterprise engagements. Translate a real legal problem into a concrete Legora workflow, then turn successful delivery into a reusable playbook others can run.
Oversee complex, multi-stakeholder programs with clear governance, owners, outcomes, leading indicators and risk management.
Build trusted relationships with Managing Partners, General Counsels, Heads of Innovation, Legal Operations leaders and other senior stakeholders.
Represent the market's voice inside Legora. Translate recurring client patterns and product gaps into clear, actionable input for Product.
Shape Legora's point of view on AI and legal work in Canada. Contribute through executive client forums, events, writing and practical market insight grounded in first-hand work.
Create clean handoffs across Go-to-Market, Legal Engineering and Engagement so that commercial momentum, delivery quality and long-term adoption reinforce one another.
Strong leadership in this role looks like this:
Hiring judgment and partnership. You treat hiring as company-building work. You own open seats end to end, partner closely with Talent and keep the bar high when growth pressure rises.
Talent development and accountability. Your team knows where they stand. Feedback is early, written and specific. You create stretch, develop future leaders and distinguish coachable gaps from persistent underperformance.
Ownership, delegation and operating rhythm. You own the market outcome while giving others real authority. Priorities, decision rights, leading indicators and dependencies are clear. The team runs well without you in every room.
Team-first leadership and culture. You give the team credit, absorb accountability for misses and create enough trust that bad news travels early. People grow faster because they worked for you.
Performance bar and decisive judgment. You protect the standard with speed, fairness and evidence. Strong performers trust you to address mediocrity, and difficult decisions remain humane and unambiguous.
The practical test is simple: the Canadian team should produce better work, stronger leaders and more repeatable customer outcomes because of the system you built, not because you personally carried every important engagement.
You may come from a leading law firm, an in-house legal function, legal operations, legal innovation, professional services, legal technology, or a combination of those worlds. The common thread is that you have moved beyond advising on change and have built the people, systems and client outcomes that make change real.
You will thrive in this role if you:
You may come from a leading law firm, an in-house legal function, legal operations, legal innovation, professional services, legal technology, or a combination of those worlds. The common thread is that you have moved beyond advising on change and have built the people, systems and client outcomes that make change real.
You will thrive in this role if you:
Are a qualified lawyer, licensed (or eligible to be licensed) in Ontario or another Canadian jurisdiction, with substantial legal, legal-operations or legal-technology experience, and a strong understanding of how sophisticated law firms and in-house legal teams make decisions.
Have built a team, function, market or new operating model from a low base, with clear evidence of what you personally decided and what continued to work without you.
Have managed and developed strong people, ideally including managers or Team Leads, and can point to people whose careers accelerated under your leadership.
Are deeply curious about generative AI and product. You do not need to be a software engineer, but you must be able to learn the platform, challenge use-case design and coach credible client work.
Can hold your own with a Managing Partner, General Counsel or executive team while remaining practical with the people doing the work.
Understand the commercial realities of legal services and enterprise software. You can connect Legal Engineering to pipeline, client value, adoption, usage and revenue.
Bring structure to ambiguity without creating process for its own sake. You build operating systems that improve speed and quality.
Have strong hiring and performance judgment. You can attract high-calibre people, develop them directly and protect the standard when a seat is not working.
Communicate fluently in English, in writing and in person. French is a strong plus.
Are based in the Greater Toronto Area and able to work from our Toronto office five days per week, with travel across Canada for strategic clients, market development and team leadership.
Global collaboration: Partner with teams and clients domestic and internationally.
Competitive package: Comprehensive salary, benefits, and tools for success.
Meaningful work: Your efforts shape how thousands of lawyers use AI daily.
In-person environment: Toronto office designed for ambitious builders.
Benefits & Perks: We invest in our people with a comprehensive, thoughtfully designed benefits package
Legora is an Equal Opportunity Employer
At Legora, we believe great teams are built on diversity of thought and experience. We’re proud to be an equal opportunity employer and committed to creating an inclusive, high-performance culture where everyone can do their best work. We welcome people of all backgrounds and don’t discriminate based on race, color, religion, national origin, gender, gender identity or expression, sexual orientation, age, disability, veteran status, or any other characteristic protected by law.
