Location(s)

We are hiring for this role to be based in the United States or Canada. This is a remote role unless you fall within the following parameters. If you live within approximately 50 miles of our San Mateo, CA or Provo, UT office, the position follows a hybrid schedule with in-office days on Mondays, Wednesdays, and Fridays.

About The Role

We are seeking a Director, Enterprise Sales to lead our enterprise sales strategy and drive revenue growth at GC AI. Reporting to Andrew Conley (CRO), you will have significant visibility into company-wide initiatives and the autonomy to shape our enterprise sales approach. You will be a strategic leader, responsible for building and leading a high-performing sales team, forging relationships with key legal industry buyers, and closing high-value deals.

We’re looking for a proven sales leader who thrives in fast-paced, ambiguous environments, with deep expertise in enterprise B2B SaaS sales, ideally in legal tech or AI-driven markets. You should have a track record of driving multimillion-dollar deals, leading teams to exceed quotas, and aligning with cross-functional teams to deliver measurable results.

What You'll Do

• Develop Enterprise Sales Strategy: Design and execute a comprehensive enterprise sales strategy to target in-house legal teams, driving pipeline growth and closing high-value deals to fuel GC AI’s revenue goals
• Lead and Build a Sales Team: Recruit, train, and mentor a high-performing enterprise sales team, fostering a culture of accountability, collaboration, and excellence
• Drive Strategic Deals: Identify, pursue, and close complex, deals with Fortune 1000 legal departments, leveraging consultative selling and relationship-building
• Optimize Sales Processes: Develop and implement scalable sales processes, including pipeline management, forecasting, and deal structuring, to ensure consistent performance
• Collaborate Cross-Functionally: Partner with Marketing, Product, Customer Success, and Partnerships teams to align go-to-market strategies, refine messaging, and enhance buyer experiences
• Leverage Technology and Tools: Utilize and implement sales technologies to streamline operations and improve team efficiency
• Track and Report Performance: Define and monitor KPIs (e.g., quota attainment, deal size, sales cycle length, win rates) to assess performance, identify opportunities, and drive data-driven decisions
• Act as a Strategic Leader: Balance hands-on deal execution with strategic leadership to set the vision for enterprise sales and contribute to GC AI’s growth roadmap

What You’ve Done

• 7+ years of experience in enterprise B2B SaaS sales, with at least 3 years in a sales leadership role
• Proven track record of leading teams to consistently exceed revenue targets and closing multimillion-dollar deals in a high-growth startup or scale-up
• Experience recruiting, training, and managing high-performing enterprise sales teams
• Demonstrated ability to design and implement sales strategies, processes, and tools to drive predictable revenue growth
• Exceptional communication and relationship-building skills, with a history of engaging C-level stakeholders (e.g., General Counsel, CLOs) and driving consensus in complex sales cycles
• Strong analytical skills, with expertise in leveraging data to run your business to optimize sales performance
• Self-starter mentality, thriving in fast-paced environments and balancing strategic planning with tactical deal execution

Nice to Have

• Experience selling to in-house legal teams or familiarity with the legal tech market.
• Knowledge of AI-driven software solutions or legal text processing.
• Proficiency with enterprise sales tools 
• Experience with sales methodologies like MEDDICC or Command of the Message.
• Track record of contributing to sales playbooks or training programs.