Director of Sales

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.

Responsibilities

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

Requirements

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 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; 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 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; passion for in-office collaboration — in-office 5 days per week

Nice to have

Experience selling into legal tech, professional services, or highly regulated industries (strong plus)

Benefits

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; Equal Opportunity Employer