Director Of Sales
legora
OnSite
Toronto
IT Governance
Job Score
80 pts
On-site model (+70)
IT Governance (+10)
About Us
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.
1,000+ customers across 50+ countries trust us, including Cleary Gottlieb, Goodwin, Linklaters, White & Case, Dentons, and Barclays. We’ve scaled to $100M+ in ARR, with teams across Europe, North America and APAC, and continue to expand through acquisitions including Qura, Walter AI and Graceview.
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.
About the Role
As a Director of Revenue at Legora, you will lead, coach, and scale a high-performing team of Account Executives (Mid-Market or Enterprise) tasked with driving top-line revenue growth across Canada.
You aren’t just a manager who sits behind a dashboard—you are a hands-on revenue leader. You will actively jump into strategic, multi-million-dollar deal cycles, architect winning go-to-market strategies, and mentor your AEs to consistently hit and exceed quota. If you thrive in a fast-paced environment, love closing complex deals, and take pride in building world-class sales talent, this is your stage.
What You'll Do
Lead, recruit, and retain a high-performing team of Mid-Market or Enterprise Account Executives.
Provide daily, high-impact coaching—from pipeline generation and discovery to complex multi-stakeholder negotiations and deal closing.
Build a culture of accountability, continuous learning, and high energy on the sales floor.
Act as an executive sponsor on high-value, complex deals (ranging into 7- and 8-figure potential ARR).
Navigate complex, highly regulated buying centers (including corporate legal teams and law firms) alongside your AEs.
Partner cross-functionally with Product, Marketing, Legal Engineering, and Executive Leadership to align GTM strategy with client needs and clear deal roadblocks.
Own your team’s revenue target, maintaining strict forecasting accuracy and pipeline health.
Develop and refine repeatable sales playbooks, qualification frameworks, and out-of-the-box prospecting tactics.
Utilize data-driven insights to analyze conversion rates, sales cycle length, and rep performance to continually optimize team output.
What You Bring
Proven Sales Leadership: 3+ years of direct sales management experience in B2B SaaS, leading teams of AEs handling complex, consultative sales cycles.
Closing Track Record: 8+ years of total B2B sales experience with a documented track record of personal and team quota attainment in high-growth environments.
Enterprise / Mid-Market Deal Mastery: Experience navigating multi-stakeholder, high-ACV deals ($100k+ to $1M+ ARR) and negotiating complex commercial terms.
Domain Experience: Experience selling into legal tech, professional services, or highly regulated industries is a strong plus.
Strategic & Operational Rigor: Highly metrics-driven with expertise in pipeline management, forecasting accuracy, and modern sales methodologies (e.g., MEDDPICC, Challenger).
High EQ & Executive Presence: Exceptional communication skills with the ability to command a room, build trust with C-level buyers, and mentor reps through tough negotiations.
Builder Mindset: Energized by fast-paced, ambiguous environments where you build processes rather than just follow them.
A passion for in-office collaboration—we are in-office 5 days per week
What’s In It For You
Global collaboration: Partner with teams and clients across Europe, APAC, and North America.
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 is designed for ambitious builders.
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.
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