About the Company

GC AI is 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 Raucho 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.

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.

What We’re Looking For

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.

Nice to Have:

Thought leader for sales through LinkedIn, webinars, community groups like Pavilion
Legal industry connections and understanding of legal buyer behavior

GC AI

Head of Sales

Remote (USA or Canada)Depending on experience/level, $300k+ OTEfull-time