Enterprise Account Executive
GC AI
Sales & Business Development
Canada · Remote
USD 150k-150k / year + Equity
Posted on Nov 26, 2025
Enterprise Account Executive
San Mateo (Hybrid) • Remote (Canada) • Remote (USA)
Sales
Remote • Remote
Full-time
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 at a $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
As our Enterprise Account Executive, you’ll lead the charge in bringing cutting-edge legal AI to the world’s most sophisticated organizations. Legal operations at enterprise scale are under immense pressure to modernize, and you’ll be the one showing them how.
Your work will directly shape how global legal teams operate, making them faster, smarter, and more strategic. The impact? Tangible productivity gains, measurable ROI, and helping Fortune 500 companies embrace the future of legal work.
We have clear product–market fit and a best-in-class AI product that legal teams already love. Now we’re scaling up-market. You’ll own complex sales cycles from discovery through procurement, navigating multiple stakeholders and driving consensus to close enterprise-level deals that move the industry forward.
Why this role matters
We currently have more inbound leads than our CEO can handle, so we need an AE who is exceptionally organized, can qualify prospects, schedule demos, manage trials, get through security questionnaires and procurement, and can close deals in record time. When you do this job right, you'll drive the adoption of AI in legal teams globally.
AI is redefining how legal teams handle work from contract review to compliance to risk analysis. Enterprises know they need to evolve, but they need a trusted partner to make it happen, and that's where you come in!
What You'll Do
- Own the full enterprise sales cycle: from initial outreach and multi-stakeholder discovery through evaluation, security review, legal, and close.
- Build and manage relationships with General Counsels, Legal Ops Directors, CIOs, and Procurement teams at global organizations.
- Lead structured pilots or proof-of-concepts, aligning technical requirements and ROI with stakeholder needs.
- Navigate complex deal structures, including security reviews, compliance, redlines, and pricing approvals, to bring deals to close.
- Collaborate cross-functionally with Solutions, Legal, and Product to deliver best-in-class enterprise buying experiences.
- Forecast accurately and manage deals through CRM (HubSpot or Salesforce) with discipline and precision.
- Continuously refine your approach from messaging and objection handling to playbooks and enterprise motion improvements.
Required Experience
- 5-10 years of quota-carrying SaaS sales experience, with at least 3 years closing enterprise deals ($100k–$1M+).
- Proven success running complex, multi-stakeholder sales cycles (Procurement, Legal, IT, Security).
- Experience selling to Legal, Compliance, or GRC teams or other highly regulated business functions.
- Exceptional written and verbal communication skills with the ability to simplify complex technology into clear business outcomes.
- Demonstrated ability to lead structured pilots, ROI analyses, and enterprise procurement workflows.
- Strong customer love.
- Relentless drive and ownership mindset, you build your own pipeline, run tight deals, and deliver results.
- Highly organized: manages 10+ active enterprise opportunities while staying on top of every detail.
- Track record of meeting or exceeding $1M+ annual quotas.
Nice to Have
- Experience selling legal tech, AI, or data-driven workflow automation solutions.
- Familiarity with security, compliance, and data privacy processes (SOC 2, DPA, InfoSec reviews).
- You’re AI-native, you use tools like Fathom, Gong, or ChatGPT daily to improve your workflow.
- Relationships or selling experience with large enterprises (Fortune 1000, law firms, or financial services).
- Experience working in high-growth startups where you built or refined the enterprise motion.
Compensation
GC AI's compensation package includes a competitive base salary benchmarked against real-time market data, as well as equity for all full-time roles. We also offer exceptional benefits, as well as commission plans for applicable roles. Our US-based compensation range for this role is $150,000 – $150,000. 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.
Req ID: R9