Director, Strategic Sales

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, Strategic 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 Strategic 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 Strategic 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 strategic/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.

A Note On Pace

We're building something new in a once-in-a-generation shift in technology and the legal industry, so we move at a relentless pace. We expect urgency, ownership, and good judgment even when things aren't perfectly clear. If you need structure and consensus to do your best work, this isn't the right place for you. If you thrive in ambiguity and growth, work with intensity, and want real responsibility, keep reading. We're excited to meet you.

Compensation

GC AI's compensation package includes a competitive base salary and commission benchmarked against real-time market data, as well as equity for all full-time roles. We also offer exceptional benefits. Our US-based compensation range for this role is: $320,000 - $380,000 OTE. Final offers may vary from the amount listed based on geography, candidate experience and expertise, and other factors.

Equal Opportunity Employment

GC AI is an equal opportunity employer that supports workplace diversity and does not discriminate on the basis of race, color, religion, gender identity/expression, national origin, age, military service eligibility, veteran status, sexual orientation, marital status, physical or mental disability, or any other protected class. GC AI is committed to working with and providing reasonable accommodation to applicants with physical and mental disabilities. #LI-GCAI

Fraud Notice to GC AI Applicants

To protect yourself against phishing and recruitment fraud, please note that GC AI only accepts job applications through our official careers page at and through sponsored jobs on LinkedIn. All legitimate communication from our team regarding job opportunities will come from a GC AI team member with a @gc.ai or @getgc.ai email address.

GC AI will never:

• Refer you to external websites to apply
• Conduct interviews over email, chat platforms, or messaging apps
• Ask you to provide payment or purchase equipment
• Request personal or financial information such as your mailing address, social security number, credit card numbers, or banking information during the application process

Examples of fraudulent email addresses:

• View email address on click.appcast.io
• View email address on click.appcast.io
• Any email address ending in @gmail.com, @yahoo.com, or other free email services

If you are contacted by someone claiming to be from GC AI via an unofficial channel or from a suspicious email address, please do not share any information. Mark the communication as "phishing" or "spam" and do not respond.