General Counsel, AI-First Legal Delivery

Own legal judgment for a $1Billion+ e-commerce brand. Make the risks behind investment decisions clear before capital is committed.
Total Annual Package: Up to USD $242,000 + comprehensive benefits (base salary + monthly performance bonus of up to 10% of base salary)

Location:
Remote (Global)
Growth path from here is fluid: broader ownership of group-wide legal strategy, with potential progression to Chief Legal Officer. What takes 4-5 years elsewhere happens in 1-2 here.
We've been AI-first since December 2023:
this role makes AI the primary production method for substantive legal work. You remain responsible for verifying sources and exercising independent judgment.
Role Overview
Puffy, a market-leading, nine-figure D2C brand and a top-five US mattress brand with over $1Billion in sales, is hiring a General Counsel, AI-First Legal Delivery to own legal work across Puffy, RGG, RGG Capital Family Office, and the CEO's personal legal matters. You'll operate within agreed mandates and approval controls and report directly to Arthur, CEO. This is a full-time, permanent, standalone in-house counsel position with no direct reports, combining hands-on AI-led production, coordination with specialist outside counsel, and personal accountability for the result.
The Problems You'll Own
Primary: Investment opportunity versus legal exposure: Family office and investment work is the primary long-term focus of this role. Fund subscriptions, side letters, custody arrangements, and lending terms can create restrictions and obligations that matter well beyond the initial transaction. The challenge is making those consequences clear before capital is committed so the CEO can decide with a practical understanding of the risks. Secondary: Broad coverage without diluted ownership: The remit spans e-commerce, corporate matters, investments, and the CEO's personal legal needs, with no internal legal team to share the work. AI can accelerate production, and outside counsel can supply specialist expertise, but neither removes the need for one accountable legal owner. The challenge is maintaining verified advice, clear priorities, and consistent follow-through across all three workstreams without urgent matters obscuring emerging risks.
The Career Accelerator
This role combines hands-on ownership of commercial, investment, and personal legal matters with a direct line to the CEO and no layers between your advice and the decision.
Your first 12 months:
Deliver a monthly Legal Exposure Audit covering material risks, deadlines, actions, unresolved decisions, and proactive recommendations across all three workstreams. Complete quarterly compliance sweeps of product pages, checkout, pricing, advertising, and terms, with evidence-backed priorities, corrective actions, and follow-through. Review and negotiate fund subscriptions, side letters, and limited partner terms before capital deployment. Review investment documents, custody arrangements, loan covenants, and counterparty controls quarterly. Personally draft, review, and negotiate vendor, retail, and affiliate agreements. Support transactions and due diligence, and coordinate disputes, regulatory inquiries, and litigation with outside counsel. Manage the CEO's personal contracts, disputes, and cross-border coordination with appropriate asset protection, estate, immigration, and tax specialists, maintaining clear boundaries for representation, conflicts, confidentiality, and authority. Use AI as the primary production method for substantive document comparison, legal research synthesis, drafting, risk analysis, and executive reporting within approved confidentiality controls. Verify decisive authorities, clauses, calculations, dates, and versions against underlying sources, and distinguish facts from assumptions. Shape legal delivery at Puffy around advice that is accurate, concise, and usable for the next decision, with clear priorities, a recommended action, an owner, and a deadline.
What Is In It For You

• Own Legal Judgment With Direct CEO Access You own the recommendation, the verification, and the follow-through. Set day-to-day legal review priorities and investigative questions, choose approved research and drafting methods, and direct approved outside counsel within its authorized scope and budget. Provide an independent legal recommendation, including when not to proceed, and obtain approval for commitments or acceptance of material risks outside your mandate. Work within your permitted professional scope and engage appropriately qualified local counsel where needed. Within your first 90 days, independently identify and flag at least five material legal risks or areas for improvement that you were not assigned to investigate, supported by evidence and practical recommendations. Contribute to live matters during onboarding, raise urgent issues promptly, give actionable interim advice when facts are incomplete,