Head of Enablement

GC AI is the trusted AI platform for in-house legal teams. We help lawyers draft, review, and analyze with precision and confidence. More than 1,000 companies use GC AI to move faster and work smarter across their legal teams, including 50+ public companies, 25+ unicorns, and brands such as News Corp, Nextdoor, Skims, Liquid Death, Vercel, Zscaler, and TIME Inc.

We've 10x'd revenue in the past 12 months, raised a $60 million Series B ($555 million valuation), and are growing faster than ever. We are backed by incredible investors, including Scale Venture Partners, Northzone, Sound Ventures, and Guillermo Rauch, CEO of Vercel. Come build the future of legal AI with us

About The Role
We are looking to add a Head of Enablement, reporting to Andrew Conley (CRO). This role offers significant autonomy and ownership in building a world-class enablement program that accelerates Account Executive (AE) onboarding, enhances value-based selling, and drives revenue growth.

We're looking for a leader who understands the foundations of sales enablement, excels at cross-functional collaboration, and has a proven track record of independently driving high-impact programs. Ideally, you've built or led enablement initiatives from the ground up, not just supported senior leaders, and are passionate about empowering sales teams to succeed in a fast-paced, AI-driven environment.

What You'll Do

• Design and Lead Enablement Strategy: Create and execute a comprehensive enablement program that equips AEs to ramp quickly, master our AI-native solutions, and articulate compelling value propositions to legal buyers.
• Develop Sales Enablement Content: Work with marketing to craft assets such as playbooks, first-call decks, demo scripts, battle cards, webinars, and training materials that highlight the value, use cases, and competitive differentiation of our solutions.
• Collaborate Cross-Functionally: Partner with Sales, Marketing (including Campaigns, Content, Web, and Corporate Marketing), and Product teams to align enablement initiatives with go-to-market strategies and ensure consistent messaging for target personas in the legal industry.
• Accelerate AE Onboarding: Build structured onboarding programs to reduce time-to-productivity, including training on product capabilities, legal industry trends, consultative selling, and objection handling.
• Drive Sales Performance: Translate marketing and industry-focused initiatives into actionable enablement programs that fuel the sales pipeline, shorten deal cycles, and improve win rates.
• Build Alignment and Engagement: Foster consensus and collaboration across Sales, Marketing, Product Management, and Customer Success to ensure enablement programs meet the needs of all stakeholders.
• Measure and Optimize: Define and track KPIs (e.g., ramp time, quota attainment, deal velocity) to assess the impact of enablement efforts and drive continuous improvement.

What You've Done

• 5+ years of experience in sales enablement, sales training, or product marketing
• B2B SaaS experience, ideally in legal tech or AI-driven software
• Proven track record of building and leading enablement programs or product launches from ideation to execution
• Exceptional communication skills, both written and verbal, with the ability to craft compelling messaging and deliver engaging training
• Strong ability to strategize, execute tactically, and lead projects in ambiguous, fast-paced environments
• Experience collaborating cross-functionally with Sales, Marketing, and Product teams to drive measurable outcomes

Nice To Have

• Familiarity with the legal domain or legal text processing.
• Experience with AI technologies
• Experience with MEDDICCC/COM frame works
• Track record of creating technical content or contributing to open-source projects.
• Proficiency with sales and enablement tools

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:

$220,000 – $258,000 OTE.

Final offers may vary from the amount listed based on geography, candidate experience and expertise, and other factors.

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.