Manager, Commercial Sales

About The Role

We are seeking a Manager, Commercial Sales to lead our SMB/Mid-Market sales strategy and drive revenue growth at GC AI. Reporting to Erik Gillespie (Senior Director of Enterprise Accounts), you will have significant visibility into company-wide initiatives and the autonomy to shape this team's sales approach. You will be responsible for building and leading a high-performing sales team, forging relationships with key legal industry buyers, and closing and expanding high-velocity deals.

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

What You'll Do

• Develop SMB/Mid-Market Sales Strategy: Design and execute a comprehensive commercial sales strategy to target in-house legal teams of companies with ~ $50-200M in revenue, driving pipeline growth and closing deals to fuel GC AI's revenue goals
• Lead and Build a Sales Team: Recruit, train, and mentor a high-performing sales team of 3 Account Executives initially, fostering a culture of accountability, collaboration, and excellence, with the ability to grow the team over time.
• Proactively Drive Deals: Identify, pursue, and close deals with mid-market 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 Proactive Leader: Balance hands-on deal execution with forward-thinking leadership to set the vision for commercial sales and contribute to GC AI's growth roadmap

What You've Done

• 5+ years of experience in B2B SaaS sales, with at least 1-3 years in a sales leadership role in SMB/Mid-Market or higher.
• Proven track record of leading teams to consistently exceed revenue targets and closing high-volume deals in a fast-paced startup or scale-up.
• Experience recruiting, training, and managing high-performing mid-market sales teams.
• Demonstrated ability to design and implement sales strategies, processes, and tools to drive predictable revenue growth
• Exceptional communication and relationship-building skills
• 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 sales tools such as Gong, HubSpot, G Suite (or similar)
• 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.

How We Work Together

GC AI is a distributed company with team members across North America, and soon Europe. We believe that because our business is AI, human connection matters more, not less. We invest in bringing people together through our hub model: regular coworking sessions, customer dinners, team and company offsites. If you're in a location without an office, expect up to 10% travel (and more for customer-facing roles).

Team members in the San Francisco Bay Area and Provo, UT (within 50 miles of the office) work together on Tuesdays, Wednesdays, and Thursdays. As we grow, we plan to establish permanent offices in more hub cities, and we will look to our team members to help build that in-person culture. We currently hire across the United States and Canada.

Perks & Benefits

We proudly offer the following benefits for our full-time employees:

Medical, Dental & Vision - Comprehensive coverage for you and your family
♥ Life & Disability Insurance - Added protection when you need it most
Retirement Plan - Plan and save for your future
Parental Leave - Time to focus on what matters most
Continuous Development - Up to $3,000/year for job-related learning & development
In-Office Meals - DoorDash credits for breakfast, lunch & dinner
Paid Time Off - 15 PTO days + 5 sick days, with opportunities to accrue more
Company Holidays - 15 company holidays + 3 additional "Me Days"
Home Office Setup - $500 for new hires to build out their workspace
Cell Phone Reimbursement - $50/month toward your phone bill
🚚 Relocation Support - Assistance to help make your move easier