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Pencil

Head of Legal

London
Posted about 19 hours ago
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About us

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.

Head of Legal

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.

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.
  • 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.

Reasons to use Rodeo

I’m in my final year doing Economics and I don’t know whether to apply for grad schemes now or do a masters first. What do you think?

Honest answer — it depends on where you want to end up. A lot of top grad schemes (Big 4, civil service, banking) don’t need a masters. Let’s look at the ones you’d be competitive for now, and we can decide if a masters actually adds anything.

Also worth knowing: most autumn 2026 applications are open now. Timing matters more than you think.

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Grad scheme, placement, apprenticeship? Not sure what you want yet — that's fine. Your agent talks it through with you and turns "I have no idea" into a shortlist.

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Graduate Consultant — 2026 Scheme

PwC·London, UK
£35,000/yr

Why you're a good match

Strong

Your economics background and your summer at a regional bank line up with what PwC looks for on the consulting scheme. Applications close in four weeks.

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It searches the market for you

Every day your agent scans the market matching roles against what actually matters to you, not just keywords on a CV.

Why you're a good match

You’ve got the grades and the economics background, and your bank internship is exactly the experience this scheme looks for. Apply soon — deadlines close within the month.

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Strong

Experience fit

Your summer at the bank plus your econometrics coursework map directly to the day-one responsibilities on this scheme — client modelling, market briefings, and deal support.

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Strong

Only hits

No noise. No "maybe this fits." Just roles with a clear explanation of why they're right — and where to focus when applying.

Your background

  • JD, LLB or equivalent law degree, and active membership in good standing of at least one state bar.
  • Minimum of 5 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.

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KPIs & Success Measures

  • 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

Benefits

  • 25 days PTO plus public holidays, although we operate a Flexible Time Off scheme
  • Health insurance / private medical cover
  • Monthly stipend towards wellness, fitness, and learning and development
  • Remote - work from anywhere in your home country
  • Enhanced parental leave policies, whether you become a parent through birth, adoption or surrogacy
  • Access to our Pencil office in The Shard, London for UK employees
  • Flexible working hours
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Skills

Commercial Law
Corporate Law
Contract Negotiation
AI Compliance
Data Privacy
GDPR
CCPA
Intellectual Property Law
Risk Management
Master Service Agreements
Data Processing Agreements
Legal Documentation
Stakeholder Management
Thought Leadership

Location

London, England, United Kingdom

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