Puffy
General Counsel, AI-First Legal Delivery
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General Counsel, AI-First Legal Delivery
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.
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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, and flag delays before deadlines are missed.
- Confirm completion with evidence and escalate unresolved dependencies.
- Reduce turnaround time and the total human effort required, including review, correction, and handoff, without lowering quality or bypassing controls.
Ownership does not itself confer signing authority or permission to deploy capital or move funds.
Join a High-Performance Organization and Partner with the 1%
🏆 Puffy: Top 5 Mattress Brand in the US with Over $1Billion USD in Sales
🌍 Great Place to Work Certified
💡 Work directly with our CEO, a Forbes Council Member. Gain firsthand exposure to the strategic decisions and high-velocity execution that drive a global brand.
Embrace Radical Flexibility
Work remotely and structure your environment around your best thinking, whether that's a home office or a co-working space. Your output is your credential, not your location.
Build Your Reputation for Decision-Ready Legal Judgment
Legal advice can arrive after a commercial decision has effectively been made. Here, your review of investment terms informs decisions before capital is committed. This scope gives you the opportunity to strengthen a distinctive combination of commercial drafting skills, judgment in reviewing investment documents, and cross-border coordination, supported by a repeatable approach to verified advice and follow-through. Puffy has been AI-First since December 2023, so you'll develop that practice with an AI-native toolbox behind you while retaining responsibility for professional judgment.
What You'll Need
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- A recognized law degree, such as a JD, LLB, or equivalent, and qualification as a lawyer in good standing in at least one jurisdiction. U.S. bar admission is not required.
- Typically 5-10 years of relevant legal experience, with the practical depth to operate without an internal legal team. Greater relevant experience is welcome.
- Demonstrate experience in commercial drafting, proactive risk identification, cross-border coordination, and management of multiple relationships with outside counsel.
- Substantial hands-on experience using AI for legal work, with examples of what you personally delivered, how you verified it, and the outcome.
- Strong executive communication skills, discretion, and follow-through.
- Must be willing to work extended hours and weekends as needed.
Good-to-Have:
- U.S. experience is a plus, not a requirement.
- Law firm and in-house experience, investment or family office exposure, and consumer protection experience are advantages.
Resources Provided
You’ll have access to our latest company-provided AI tools, including ChatGPT, Claude, multiple AI agents, bots, plugins, AI projects, and automations through platforms such as n8n. You’ll also receive the department tools, relevant data, assets and specialist support needed to deliver your work. We expect you to use these resources to automate routine work and deliver high-quality results quickly.
The Puffy DNA
We're restless, perpetually hungry, and fast-paced, driven by an unwavering belief that we can outperform any competitor, regardless of their size.
- Be the Owner: We don't hire employees; we welcome owners. You're accountable for results, not activity.
- Execute with Urgency: We thrive in high-stakes environments by making thoughtful decisions quickly and acting decisively.
- Demand Excellence: We solve the hard problems that others can't, pushing the boundaries of our craft.
- Be AI-First: Daily multi-turn AI conversations challenge your assumptions.
- Go All-In: When the mission demands it, we rally as one team to cross the finish line.
Your Total Compensation & Benefits
💰 Compensation:
Total Annual Package: Up to USD $242,000 + comprehensive benefits (base salary + monthly performance bonus of up to 10% of base salary)
Annual salary review every January
🏥 Health & Protection:
Comprehensive medical, dental, and vision insurance (based on the country of hire)
🌴 Time Off:
Generous Paid Time Off (PTO) + public holidays
💼 Work Environment:
AI-First organization with access to an AI-native tool stack
Remote First: Work from the comfort of your home office
Learning & development opportunities
International team collaboration across 16+ nationalities. Your assumptions get challenged daily.
🏆 Rewards & Recognition:
Eligibility for selection to the Leaders Club, an elite recognition program featuring premium wellness memberships, exclusive networking with senior leadership, and annual leadership retreats
Eligibility for nomination as 'We Are' Champion of the Month, monthly recognition with gift vouchers and company-wide celebration for exceptional contributions
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