Manager, SMB Account Executives (AI SaaS)

TL;DR

Manager, SMB Account Executives (AI SaaS): Lead and scale a team of approximately five SMB Account Executives selling an AI-native legal workspace, with an accent on coaching, pipeline execution, and predictable revenue delivery. Focus on improving sales conversion, navigating complex multi-stakeholder deals, building playbooks, and maintaining accurate forecasts.

Location: On-site in Chicago, United States

Salary: $212,000–$250,000 per year, plus equity and commission.

Company

Legora develops an AI-native workspace that helps legal professionals analyze documents and manage end-to-end legal workflows.

What you will do

• Lead, mentor, and develop approximately five SMB Account Executives through 1:1s, call coaching, and pipeline reviews.
• Own aggregate SMB quota attainment and maintain a healthy, predictable sales pipeline.
• Support complex deals, including objection handling, multi-stakeholder evaluations, and closing negotiations.
• Improve inbound lead routing, outbound prospecting strategies, and sales playbooks with Sales Operations and Marketing.
• Recruit, onboard, retain, and develop sales talent.
• Track quota attainment, pipeline velocity, conversion, forecast accuracy, retention, and ramp time.

Requirements

• 4+ years of B2B SaaS sales experience, including 2+ years managing or leading SMB or Mid-Market Account Executives.
• Consistent record of meeting or exceeding team quota targets and driving predictable revenue growth.
• Strong coaching skills across discovery, multi-stakeholder alignment, objection handling, and urgency building.
• Proficiency in CRM hygiene and funnel analysis using Salesforce or HubSpot.
• Ability to work in a fast-paced environment and create effective sales playbooks.
• Ability to work on-site in the Chicago office.

Culture & Benefits

• High-ownership, low-ego culture focused on impact, excellence, and continuous improvement.
• Collaboration with teams and clients across Europe, APAC, and North America.
• Company-provided daily lunch in the Chicago office.
• Medical, dental, and vision coverage with Aetna, Kaiser Permanente, MetLife, and Vision Care options.
• Parental leave, Maven Clinic access, dependent care FSA, and One Medical membership.
• 401(k) with company match, unlimited PTO, commuter benefits, life insurance, disability coverage, and additional voluntary benefits.