Head of Legal

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. To achieve this, we need to make sure that our technology isn’t just in the hands of big brands - we need to try to help small businesses and creative individuals too.

We’re looking for a Head of Legal who will lead our legal operations, ensuring our client and vendor contracting processes align with our business strategy, evolving legal standards, and risk management requirements. To do this successfully, you'll need to understand the rapidly changing GenAI regulatory environment, expertly navigate complex contract negotiations, and position Pencil as a trusted leader in AI compliance and best practices.

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  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.

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  Oversee agreements with AI technology vendors, ensuring vendor terms effectively align back-to-back with Pencil’s client obligations.

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  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 rather than after the fact.

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  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.

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  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.

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  Consult with client legal teams to clearly communicate and validate Pencil's legal and technical safety protocols, facilitating trust and compliance.

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  Create thought leadership content such as whitepapers and participate in speaking engagements about legal issues related to Generative AI in marketing.

• 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.

• Average MSA/T&Cs redline-to-signature cycle time

• % of client contracts closed without material deviation from Pencil's standard paper

• DPAs, Privacy Policy, and T&Cs reviewed/updated on a fixed cadence