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Pencil is an advertising technology company leveraging generative AI to transform content creation. The company's mission is to democratize AI-powered advertising tools for businesses of all sizes, from enterprises to small businesses and creative individuals.
As Head of Legal, you will lead all legal operations and establish Pencil as a trusted authority in AI compliance and regulatory best practices. You'll own the full lifecycle of client and vendor contracts, from negotiation through execution, ensuring alignment with business strategy and evolving legal standards.
Key responsibilities include:
- Negotiate and manage complex client contracts, including Master Service Agreements (MSAs) and Terms & Conditions, balancing business objectives with risk management
- Oversee vendor agreements with AI technology providers, ensuring back-to-back alignment with client obligations
- Develop and maintain legal documentation (T&Cs, Data Processing Agreements, Privacy Policies) in line with AI regulatory evolution
- Consult with client legal teams to communicate Pencil's legal and technical safety protocols, building trust and ensuring compliance
- Create thought leadership content (whitepapers, speaking engagements) on generative AI legal issues in marketing
You'll be measured on MSA/T&C redline-to-signature cycle time, percentage of contracts closed without material deviations from standard terms, and cadence of legal document reviews and updates.
Required qualifications: JD, LLB, or equivalent law degree with active bar membership in at least one jurisdiction. Minimum 5 years as a commercial or corporate attorney with specific AI space experience. Proven track record negotiating complex contracts, including 8-figure enterprise deals. Deep expertise in data privacy (GDPR, CCPA) and intellectual property law. Strong ability to translate complex legal concepts for diverse stakeholders. Prior experience with industry whitepapers or speaking engagements is highly desirable.
