Head of Design, AI-First

Own the design function for a $1Billion+ brand. Transform how we build with AI.

Total Annual Package: Up to USD $132,000 + comprehensive benefits (Base salary + monthly performance bonus of up to 10% of base)

Location: Remote (Global)

Growth path from here is VP Design → Chief Design Officer. What takes 4-5 years elsewhere happens in 1-2 here.

We've been AI-first since December 2023: Every design proposal ships with an AI review link, and Figma AI runs in our live production pipeline, shipping real work. You'd start where most teams are still trying to get.

This position is remote, with the option to work from our Dubai office (with 0% income tax), if preferred (relocation and visa sponsorship support available).

Role Overview

Puffy, a market-leading, nine-figure D2C brand and Top 5 US mattress brand with over $1 billion in sales, is hiring a Head of Design to own end-to-end web design with full authority over the design system, the AI-first workflow, the conversion roadmap, accessibility standards, and a team of three designers, reporting directly to the CEO.

This role exists to turn design from a sequential production queue into a fast, AI-native operation, building the workflow, prompt infrastructure, and system governance that let high-quality work ship at volume without the CEO adjudicating timelines.

The Career Accelerator

This is not a role where you review other people's mockups and forward them to engineering. The scope is scarce: very few Heads of Design get simultaneous authority over the design system, the AI toolchain, the conversion roadmap, accessibility standards, and a team of 3, with a direct line to the CEO and no layers in between.

Your first 12 months: rebuild the design workflow from sequential to agile, with kickoff huddles and a handoff-time reduced by 40%. Build the prompt library and review workflow covering product copy, FAQs, size/fit guidance, policy explainers, and localized variants. Design the UI patterns for conversational search, guided finders, and PDP Q&A alongside engineering. Own the recommendation surfaces — placements, card density, "why this" microcopy — and validate them with staged rollouts. Evolve the design system so tokens and components absorb AI-generated variants without brand drift or PageSpeed cost. Bake WCAG 2.2 into the system and pair AI-assisted audits with manual review. Set the split with Growth between bandit allocation on evergreen surfaces and classic A/B on high-stakes causal changes. Shape the future of design at Puffy, where the site is the entire storefront and every conversion point runs through your team.

What Is In It For You

This isn't just another design management role. This is your chance to become a true industry architect.

1. Own the Design Function and the Toolchain It Runs On

You set the standard, build the workflow, and own what ships.

• You design the operating model for the whole function: how work enters the queue, how AI-generated variants get validated, where human QA sits, and how a spec reaches Dev Mode without losing intent. You own IA, wireframes, high-fidelity comps, prototypes, and motion specs across Home, PLP, PDP, Cart/Checkout, editorial, and paid-media landing pages. You decide what the design system tolerates and what it rejects.
• You hold the line on WCAG 2.2, PageSpeed, and brand consistency while the volume goes up, and you carry the conversion roadmap in your own numbers. You report to the CEO directly, present quarterly roadmap reviews, and translate design decisions and experiment results into the narrative the business acts on.

2. Join a High-Performance Organization and Partner with the 1%:

🏆 Puffy: Top 5 Mattress Brand in US with Over $1 Billion USD in Sales

🌍 Great Place to Work Certified

💡 Work directly with Forbes Council Member CEO. Your vision is the company's vision.

Gain firsthand exposure to strategic decisions and high-velocity execution that drives a global brand

3. Embrace Radical Flexibility

Work from anywhere in the world with meaningful time zone overlap. Structure your environment around your best thinking, whether that's a home office, a co-working space, (OR) our Dubai headquarters (with full relocation, visa support, and 0% income tax if you choose). Your output is your credential, not your location.

4. Become the Design Leader Other Brands Come Looking For

In most companies, design leaders inherit a workflow somebody else built and spend their tenure defending its timelines in meetings. Here you build it. When the CEO decides what ships next quarter, your roadmap is the input to that decision, not a status report on it afterwards. You'll leave with an AI-native design operation you designed end to end — and the handoff-time and conversion numbers proving quality held while volume went up, which is the part almost nobody in this function can actually show. Puffy has been AI-First since December 2023, so you'll build it with an AI-native toolbox behind you rather than a versioning queue in front of you.

What You'll Need

• 7+ years in web design for e-commerce, including 4+ years leading, mentoring, and managing the operations of a design team.
• A portfolio that shows shipped PDP/PLP/Checkout improvements tied to clear business metrics.
• Expert in Figma (components, variables, Dev Mode); strong visual/motion craft and responsive design sensibility.
• Proven experience implementing GenAI tools into a professional design pipeline, with a clear understanding of prompt engineering, quality control, and brand governance.
• Familiarity with AI-shaped UX patterns: conversational search, assistant UI, recommendation modules, and their measurement.
• Comfort collaborating on experiments (A/B vs multi-armed bandits) with Growth; understands trade-offs between optimization speed and causal certainty.
• Working knowledge of WCAG 2.2 and SEO fundamentals for structured content and schema on e-commerce sites.

Good-to-Have

• Experience designing chat or guided-selling flows

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 $132,000 + comprehensive benefits (Base salary + monthly performance bonus of up to 10% of base)
• Annual salary review every January

🏥 Health & Protection:

Comprehensive medical, dental, and vision insurance (based on country of hire)

🌴 Time Off:

Generous Paid Time Off (PTO) + Public holidays

💼 Work Environment:

• AI-First organization with access to 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

Ready to Shape Your Story?

Click "Apply" and take the first step.