Sales Manager, SMB

In this onsite leadership role in Chicago, you will manage and grow a small team of SMB Account Executives at Legora. You will coach deal execution, maintain high standards for pipeline and forecasting accuracy, and help drive predictable revenue outcomes across the SMB segment.

Role Overview

As Manager, SMB Account Executives, you will lead a team of approximately 5 reps. Your focus will be to scale execution of the SMB sales strategy, mentor through complex sales cycles, and ensure the team meets and exceeds revenue targets.

Key Responsibilities

• Lead, coach, and scale a high-performing team of approximately 5 SMB Account Executives.
• Drive execution of Legora’s small-business sales strategy to ensure team revenue targets are met or exceeded.
• Manage pipeline and forecast accuracy to support reliable reporting.
• Actively mentor reps through complex deal cycles, including refining pitching mechanics.
• Foster a culture of continuous improvement through structured coaching and review.
• Run weekly 1:1s, provide live call coaching, and conduct pipeline reviews to elevate sales acumen and execution.
• Own the aggregate quota for the SMB segment.
• Ensure a healthy, predictable pipeline and accurate monthly and quarterly revenue forecasts.
• Join and support reps on deals as needed to help advance complex opportunities to close.
• Support reps in objection handling, multi-stakeholder evaluations, and closing negotiations.
• Partner with Sales Operations and Marketing to refine inbound lead routing, outbound prospecting strategies, and internal sales playbooks.
• Recruit, onboard, and retain top-tier sales talent.
• Build a clear path for Account Executives to grow within the revenue organization.

Requirements

• 4+ years of B2B SaaS sales experience.
• 2+ years of direct management or team lead experience overseeing SMB or Mid-Market Account Executives.
• Track record of consistently meeting or exceeding team quota targets and driving predictable revenue growth.
• Strong commitment to people development.
• Ability to diagnose skill gaps in the sales cycle and coach reps on discovery, multi-stakeholder alignment, and urgency building.
• Proficiency in CRM hygiene using Salesforce and/or HubSpot, and using data to identify bottlenecks in the sales funnel.
• Comfort operating in a fast-paced, evolving environment.
• Experience building playbooks, not only executing existing processes.

Technologies

• Salesforce
• HubSpot

Key Results and Metrics

• Percentage of the team meeting or exceeding individual quarterly revenue targets.
• Improvement in team win rates and average sales cycle length.
• Variance between committed forecast and actual revenue closed by quarter end.
• Successful onboarding to productivity with low regrettable attrition.

Compensation

Compensation range: USD 212,000 - 250,000 per year.

Benefits

• Comprehensive salary, benefits, and tools for success.
• Global collaboration across Europe, APAC, and North America.
• In-person environment in the Chicago office, with company-provided lunch daily.
• Medical, Dental & Vision coverage.
• Multiple medical plan options through Aetna and Kaiser Permanente.
• HSA or Healthcare FSA based on plan selection.
• Dental plans via MetLife and vision plans via Vision Care.
• Generous parental leave.
• Free access to Maven Clinic.
• Dependent Care FSA.
• Free One Medical membership for employees and dependents.
• Pre-tax commuter benefits.
• Life Insurance plus 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.