Sales Manager, SMB Chicago

Legora AB; Chicago (IL); On-site; USD 90,000 - 130,000; Full time

Benefits offered by this job

Medical benefits

Dental benefits

Vision benefits

401K match

Unlimited PTO

Commuter benefits

Life Insurance

Job summary

Legora AB, based in Chicago, seeks a Manager of SMB Account Executives to lead a small team and drive revenue growth. You will coach reps through complex deals, refine pitching, and ensure a strong, scalable SMB sales program.

The role emphasizes hands-on leadership, forecast discipline, and continuous improvement within a fast-paced, global AI-native sales environment.

Qualifications

• 4+ years of B2B SaaS sales experience, with at least 2+ years of direct management or team lead experience overseeing SMB or Mid-Market Account Executives.
• Proven track record of meeting or exceeding team quota targets and driving predictable revenue growth.
• Coaching mindset with ability to diagnose skill gaps in a sales cycle and coach reps on discovery, multi-stakeholder alignment, and urgency building.
• Data-driven with CRM hygiene (Salesforce/HubSpot) and using data to identify bottlenecks in the sales funnel.
• Adaptable in a fast-paced, evolving environment; able to build playbooks, not just execute existing ones.

Responsibilities

• Lead and mentor a team of ~5 SMB AEs with weekly 1:1s, live call coaching, and pipeline reviews to elevate sales execution.
• Own the aggregate SMB quota; ensure healthy pipeline and accurate monthly/quarterly forecasts.
• Actively assist in deals to support reps; navigate objections, multi-stakeholder evaluations, and closing negotiations.
• Partner with Sales Ops and Marketing to refine inbound/outbound lead routing and internal sales playbooks.
• Recruit, onboard, and retain top-tier sales talent with clear growth paths within the revenue organization.
• Measure success by team quota attainment, pipeline velocity, forecast accuracy, and ramp time.

Job description

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.

The Role

As the Manager, SMB Account Executives, you will lead, coach, and scale a high-performing team of approximately 5 SMB Account Executives. You will be responsible for driving the execution of our small-business sales strategy, ensuring your team meets and exceeds their revenue targets.

This is a role where you will not only manage pipeline and forecast accuracy but also actively mentor reps through complex deal cycles, refine their pitching mechanics, and foster a culture of continuous improvement.

What You’ll Do

• Team Leadership & Coaching: Manage and mentor a team of ~5 SMB AEs. Conduct weekly 1:1s, live call coaching, and pipeline reviews to elevate the team’s sales acumen and execution.

• Revenue Delivery: Own the aggregate quota for the SMB segment. Ensure the team maintains a healthy, predictable pipeline and accurately forecasts monthly and quarterly revenue.

• Sales Execution: Actively jump into deals to support your reps. Help navigate objections, multi-stakeholder evaluations, and closing negotiations.

• Process Optimization: Partner with Sales Operations and Marketing to refine inbound lead routing, outbound prospecting strategies, and internal sales playbooks.

• Talent Development: Recruit, onboard, and retain top-tier sales talent. Build a clear path for AEs to grow within the revenue organization.

• Key Results & Metrics

  Success in this role will be measured by performance against key metrics, including:

  • Team Quota Attainment: Percentage of the team meeting or exceeding their individual quarterly revenue targets.

  • Pipeline Velocity & Conversion: Improvement in the team's win rates and average sales cycle length.

  • Forecast Accuracy: The variance between your committed forecast and actual revenue closed at the end of the quarter.

  • Team Retention & Ramp Time: Successfully onboarding new hires to productivity quickly and maintaining low regrettable attrition.

What You Bring

• Experience: 4+ years of B2B SaaS sales experience, with at least 2+ years of direct management or team lead experience overseeing SMB or Mid-Market Account Executives.

• Proven Track Record: A history of consistently meeting or exceeding team quota targets and driving predictable revenue growth.

• Coaching Mindset: Deep passion for people development. You know how to diagnose skill gaps in a sales cycle and coach reps on discovery, multi-stakeholder alignment, and urgency building.

• Data-Driven: Proficient in CRM hygiene (Salesforce/HubSpot) and using data to identify bottlenecks in the sales funnel.

• Adaptability: Thrives in a fast-paced, evolving environment. You are comfortable building playbooks, not just executing existing ones.

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: 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 through 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

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.