GC AI is currently an AI platform for in-house lawyers to 10x themselves. Using the latest LLMs, we are building AI agents that can use company knowledge, leverage external sources, and connect with internal tools to provide better and faster legal advice to the rest of the company. Thousands of weekly active users tell us they “cannot imagine their lives without GC AI” - which has led us to 95% retention and a NPS of 75.
This is a once-in-a-generation opportunity to build for a $1T annual market. We have jaw-dropping product-market fit - growing our customer base from 0 to 500+ legal teams in a year and 3X ARR growth in the last 4 months. Join our Series A stage rocket ship backed by top investors like Sound Ventures, Fellows Fund, Guillermo Rauch and Worklife Ventures. GC AI is a small but mighty team of lawyers, engineers, sellers and doers. Here, you’ll have infinite room to grow and rethink how legal work gets done.
Come build the future with us.
About the role:As our first Head of Sales, you'll be defining how we scale from $5M to $40M+ ARR while maintaining our product-led growth magic. Your impact will be foundational and lasting. The best part? The product is great and customers are clamoring for it. We have clear, deep product-market fit, but we need a sales leader to help us systematically capture the massive demand we're seeing.
This role requires both strategic revenue leadership and hands-on deal execution. You're comfortable with the strategy of scaling enterprise sales in a PLG environment and the scrappiness of closing your own deals when needed. You're a curious person who wants to dig into the details of how legal teams buy, and you have strong opinions about modern sales using AI and building revenue engines that enterprise buyers trust. You'll shape how our sales process is structured, how our team is built, and how legal teams adopt AI for the first time. You'll have the runway to build the sales org from scratch, evolve our pricing and packaging, and influence product direction in partnership with the CEO and CTO.
Why this role matters:As our first Head of Sales, you'll be defining how we scale from $5M to $40M+ ARR while maintaining our product-led growth magic. Your impact will be foundational and lasting. The best part? The product is great and customers are clamoring for it. We have clear, deep product-market fit, but we need a sales leader to help us systematically capture the massive demand we're seeing.
This role requires both strategic revenue leadership and hands-on deal execution. You're comfortable with the strategy of scaling enterprise sales in a PLG environment and the scrappiness of closing your own deals when needed. You're a curious person who wants to dig into the details of how legal teams buy, and you have strong opinions about modern sales using AI and building revenue engines that enterprise buyers trust. You'll shape how our sales process is structured, how our team is built, and how legal teams adopt AI for the first time. You'll have the runway to build the sales org from scratch, evolve our pricing and packaging, and influence product direction in partnership with the CEO and CTO.
What you'll do:
Revenue Engine & Scale: Own and execute our path from $5M to $40M+ ARR. Build scalable sales processes that leverage our PLG foundation while capturing enterprise deals. Balance high-velocity sales with strategic enterprise account development.
Team Building & Leadership: Recruit, hire, and develop a world-class sales team with a structured yet supportive approach. Ideally, you have a strong network - developed through your involvement in a sales community like Pavilion, thought leadership on Linkedin, etc.
Develop Playbooks: Become obsessed with our ideal customer profile and develop playbooks for scalable, repeatable deals with midmarket customers.
Strategic Account Development: Develop and execute enterprise ABM strategies while maintaining our PLG efficiency. Build relationships with key accounts and create repeatable processes for enterprise acquisition and expansion.
Hands-On Deal Execution: Close your own strategic deals while coaching your team. Lead by example in complex enterprise sales cycles and maintain deep customer relationships that drive expansion and referrals.
Product Partnership & Evolution: Work closely with product teams to understand and advocate for our AI capabilities. Drive pricing and packaging evolution as we add new products and potentially move to usage-based models. Bring customer insights back to influence product roadmap.
Systems & Operations:Use revenue operation tools and AI to automate and create scalable processes that support high-velocity growth with hundreds to thousands of customers.
Minimum 7+ years of progressive sales leadership experience with proven success being part of the team that scaled B2B companies from $5M to $40M+ ARR
Experience in a company that grew from PLG to sales-led and successfully managed both - e.g. companies like Vercel, Carta, Ashby, Vanta, Drata, Datadog, Snowflake, Canva, Asana, or Airtable
Experience with a complex buyer such as regulated industries, technical buyers or discerning buyers (legal, finance, compliance, technical leaders)
Experience building and developing a world-class sales team through a structured yet supportive approach
Hands-on execution mindset - willing to close your own deals, not just manage others. Proven track record of personal quota achievement alongside team leadership.
Product fluency with ability to understand and use technical products. Experience with pricing evolution, packaging changes, and translating customer feedback into product insights.
AI fluent with demonstrated ability to articulate how AI has impacted sales team - and how to incorporate it into sales operations
Experience working closely with VC-backed founders and thrive in high-intensity environments.
You have experience in legal tech or have previously sold technology solutions to legal professionals.
You use AI in business yourself and/or are AI native yourself (you use Fathom, Gong, or other AI tools)
Familiar with compliance-related aspects of selling software, like SOC II, vendor qualification, and other items that need to be completed to get to launch/close.
Growth & Impact
Shape the future of a rapidly growing startup
Direct collaboration with founding team
Real influence on company strategy and direction
A voice that matters - your ideas will be heard and implemented
Environment & Benefits
Competitive salary, equity and healthcare
We’re a hybrid company — many roles are remote-friendly, while some teams require meeting in person a couple of days a week in the Bay Area office.
High-energy, joyful team environment
Career Development
Mentorship and learning opportunities
Clear path for growth in an expanding company
Exposure to cutting-edge technologies and practices
Freedom to innovate and own crucial systems
GC AI Compensation & Benefits Highlights
How does GC AI ensure its pay and bonus plans are competitive?
GC AI ensures its pay and bonus plans are competitive through a structured and transparent compensation approach. The company publishes pay transparency, uses defined pay bands with transparent earning potential, and sets defined commission tiers and policies for applicable roles. Its compensation package also includes company equity and a 401(k), giving employees a clear view of both immediate pay and long-term financial upside.
GC AI reinforces that compensation philosophy with practices that create consistency and clarity across the employee experience. The company promotes from within, supports learning and development, and maintains defined working hours, availability expectations, and goal-setting through an OKR operating model. For job seekers, that signals a workplace where compensation is tied to clearly established expectations, growth opportunities, and a rewards structure designed to stay competitive as the company scales.
GC AI Insights
What We Do
GC AI is the leading legal AI platform built specifically for in-house teams to solve the high-precision workflows they face every day. With powerful features like Easy Prompt™, Exact Quote™ citations, and native Microsoft Word integration, GC AI enables legal professionals to be strategic business partners through faster and more accurate drafting, reviewing, researching, and redlining. Purpose-built for sensitive, high-stakes matters, the platform leverages five large language models while maintaining enterprise-grade security as a SOC 2 Type II certified provider that never uses confidential data for training. Founded by three-time General Counsel Cecilia Ziniti and AI engineer Bardia Pourvakil, GC AI is trusted by over 1,600 legal teams globally, including brands like News Corp, Skims, TIME Inc., Liquid Death, and Vercel. Discover the difference of becoming an AI-powered lawyer. Try it free or book a demo at gc.ai.
Why Work With Us
GC AI offers a rare opportunity to join a high-growth category leader at the intersection of generative AI and deep legal expertise. Our culture is defined by a "1% better every day" philosophy, favoring curious, customer-obsessed builders who thrive in a high-ownership environment where they can see the immediate impact of their work.
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GC AI Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
Many roles are eligible for remote work in the U.S. and Canada. For folks who live within 50 miles of our San Mateo, CA, or Provo, UT offices, we value in-person collaboration and work in the office on Tuesday, Wednesday, and Thursday.
