Director of Revenue
- Location
- Chicago, IL · On-site
- Job type
- Full-time
- Level
- Director
- Experience
- 3+ years
- Listed
- 23 days ago
Skills & highlights for this role
- MEDDPICC
- forecasting
- pipeline management
- complex multi-stakeholder deal negotiation
Also useful
- Challenger sales methodology
Stated benefits & perks
- Health
- Dental
- Vision
- 401k match
- Unlimited pto
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 the Central region.
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.
- In-Office Collaboration: A passion for dynamic, in-person teamwork-we collaborate 5 days per week in our Chicago office.
What's In It For You
- Global collaboration: Partner with teams and clients across Stockholm, New York, London, and Sydney.
- Competitive package: Comprehensive salary, benefits, and tools for success.
- Meaningful work: Your efforts shape how thousands of lawyers use AI daily.
- In-person environment: Chicago office designed for ambitious builders and company provided lunch daily.
- Benefits & Perks: We invest in our people with a comprehensive, thoughtfully designed benefits package:
Medical, Dental & Vision
- Multiple medical plan options via Aetna and Kaiser Permanente
- HSA or Healthcare FSA (based on plan selection)
- Dental plans via MetLife
- Vision plans via Vision Care
Family Support
- Generous parental leave
- Free access to Maven Clinic
- Dependent Care FSA
- Free One Medical membership for employees and dependents
Additional Perks
- Pre-tax commuter benefits
- Life Insurance + STD/LTD
- 401(K) with generous company match
- Unlimited PTO
- Robust voluntary benefits, including identity protection (via Aura), legal coverage via MetLife, pet savings programs, and more
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.
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.
Equal opportunity and legal notices
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.
From Legora's careers page, first listed on Rolev.ai on October 17, 2026. Rolev.ai is not the employer.
How Rolev.ai helps with this application
Rolev.ai is a job search and application tool for US job seekers. For this Director of Revenue role at Legora, it shows how your resume fits, tailors your resume to the posting, and prepares the application for you to review.
See how you fit
Openings from employer career sites are ranked against your whole resume—and searchable inside Claude, ChatGPT, and Cursor via Rolev.ai MCP.
Tailor without inventing
Every change to your resume is checked against your original. New experience goes in only with your yes—zero fabricated claims.
Draft the full kit
Tailored and Full Match resumes, role-specific cover letters, and answers to employer screening questions are prepared in seconds.
1-Click Extension Autofill
The Chrome extension fills the employer's Greenhouse, Workday, Lever, or Ashby form in 1 click. You review it and press Submit.
Similar roles
All Sales Manager jobs- Sales ManagerProFormance Builder Solutions · Fort Myers, FL · $60k – $70k/yr
- Sales Manager - Visalia, CAScotts Miracle-Gro · Visalia, CA · $71.4k – $84k/yr
- Area Sales ManagerSnap Finance · Philadelphia, PA
- Sales Manager, MVNidec · Brooklyn Heights, OH
- Senior Lead Logistics Product Business Development ManagerMaersk · Charlotte, NC
- RVP, Sales, Slack, Federalsalesforce · Mclean, VA
Common questions
Where is the Director of Revenue job at Legora located?
This Director of Revenue position at Legora is located in Chicago, IL (On-site). Always check Legora's application page for specific state eligibility or relocation policies.
What qualifications are required for Director of Revenue at Legora?
For the Director of Revenue role, Legora highlights 3+ years of relevant experience; experience with MEDDPICC, forecasting, pipeline management, complex multi-stakeholder deal negotiation. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.
How do I apply for the Director of Revenue position at Legora?
This listing links directly to Legora's Ashby application page. You can apply directly on Legora's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Ashby application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.