Head of Legal (Generative AI & Advertising Tech)

About Pencil: At Pencil, we are driving innovation in advertising technology through our state-of-the-art SaaS product, which harnesses Generative AI to redefine content creation. Our mission is to make AI the default in advertising without replacing creative people. We aim to democratize access to our technology for small businesses and creative individuals.

We are seeking a Head of Legal to lead our legal operations, ensuring our client and vendor contracting processes align with our business strategy, evolving legal standards, and risk management requirements. This role requires deep expertise in the rapidly changing GenAI regulatory environment, the ability to negotiate complex contracts, and positioning Pencil as a trusted leader in AI compliance and best practices.

Key Responsibilities:

• Negotiate and manage client contracts, including redlining Master Service Agreements (MSAs) and Pencil’s standard Terms & Conditions to ensure alignment with business objectives and risk management.
• Oversee agreements with AI technology vendors, ensuring vendor terms effectively align back-to-back with Pencil’s client obligations.
• Act as embedded legal counsel to product teams, reviewing new features and AI capabilities for legal and regulatory risk before launch, and advising on design decisions in real time.
• Monitor the evolving AI and data regulatory landscape (e.g., EU AI Act, GDPR, sector-specific guidance) and proactively brief product and leadership on implications, translating regulatory change into practical product and commercial strategy.
• Develop, maintain, and continuously update Pencil’s legal documentation, such as Terms & Conditions, Data Processing Agreements (DPAs), and Privacy Policies, keeping pace with advancements in AI technology.
• Consult with client legal teams to clearly communicate and validate Pencil's legal and technical safety protocols, facilitating trust and compliance.
• Create thought leadership content such as whitepapers and participate in speaking engagements about legal issues related to Generative AI in marketing.

Your Background:

• A JD, LLB, or equivalent law degree, and active membership in good standing of at least one state bar.
• Minimum of 7 years of experience as a commercial or corporate attorney, specifically within the AI space.
• Proven experience in negotiating complex contracts with clients and technology vendors.
• Experience handling 8-figure deal value contracts with enterprise-scale clients.
• Deep understanding of data privacy regulations (e.g., GDPR, CCPA) and intellectual property law.
• Strong ability to clearly communicate complex legal concepts to diverse stakeholders.
• Previous experience in drafting industry whitepapers or speaking engagements is highly desirable.

KPIs & Success Measures:

• Average MSA/T&Cs redline-to-signature cycle time
• Percentage of client contracts closed without material deviation from Pencil's standard paper
• DPAs, Privacy Policy, and T&Cs reviewed/updated on a fixed cadence