Design Lead

Pickle•New York City, NY

2d•Onsite

About The Position

Pickle is a peer-to-peer rental marketplace unlocking the value of the billions of underutilized items sitting in consumers' closets. We make it easy to rent high-quality items exactly when you need them — with fast, convenient fulfillment and an on-demand experience that's as seamless as shopping. We're building a new kind of commerce layer: one powered by dynamic local supply, where access is more convenient than ownership. Pickle is now live nationwide and scaling rapidly in key local markets including NYC, LA, and Miami. Our marketplace already features 400K+ items, and we're just getting started. We're excited to extend our vision beyond fashion into every category. What makes Pickle different is the combination of incredible peer-to-peer inventory, industry-leading convenience (under 2 days nationwide and under 2 hours locally), and an on-demand model with no subscriptions — users rent what they want, when they want it. We've raised $20M to date from FirstMark, Craft, Burst Capital, FJ Labs, and others, and we're scaling quickly to build the future of access-driven shopping. About the role We're looking for a Design Lead who comes from consumer product and who is genuinely excited to get more technical. You have deep instincts for how consumers actually use applications and what makes a marketplace feel alive. You have developed both taste and a deep understanding of the customer-voice from working in consumer and you want to pair it with a company that is going to let you ship directly into the codebase. Over time you will help build a team, but this will initially be a senior IC role. You are the person setting and defending the design bar for Pickle across every surface including the renter experience, the lender experience, the marketplace web experience, marketing, and every new category we launch. Pickle is establishing a Builder Model. You will ship prototypes through AI tools. You work in Figma when Figma is the right tool, and you work in Cursor/Claude Code when code is the right tool. You don't need to be a senior frontend engineer on day one — but you need to be genuinely excited to code more than you do today, AI-fluent in your daily workflow, and comfortable opening a PR to adjust spacing or tune an animation instead of filing it as a ticket. If you're a senior consumer product designer who has been quietly learning to ship in code, who uses Cursor or Claude Code daily, and who wants to stop throwing work over a wall at a company that is actually going to let you run — this is the role.

Requirements

5+ years of product design experience at consumer companies.
Shipped consumer product at scale, and preferably consumer marketplace.
Strong instincts for consumer experiences; a point of view on how real people use consumer platforms.
Demonstrated craft in visual design, typography, interaction, and motion.
Genuine excitement to get more technical.
Already using AI coding tools in your daily workflow (Cursor, Claude Code, or similar) and ready to ship changes directly in a codebase.
Eagerness to close the gap to being a senior engineer fast, not reluctantly.
Comfort (or excitement to learn) reading code in a modern frontend stack.
Ability to navigate the codebase, make small changes confidently, and improve every month.
Comfort (or excitement to learn) operating in a Builder Model where handoffs are limited.
Direct, low-ego, high-output approach.
Ability to give real feedback and ship fast.
Desire to work closely with founders.
Based in NYC or willing to relocate.
This is an in-office role.

Nice To Haves

B2B or enterprise-only candidates are not the right fit for this role.

Responsibilities

Own the consumer experience end to end and be accountable for making it seamless, smooth, and enjoyable.
Set the bar for visual design, typography, motion, and interaction across every surface (mobile, web, marketing, new markets, new categories, etc.) and defend it across the company.
Design the core loops that renters and lenders move through every day, and obsess over the friction points that cost Pickle transactions.
Design how inventory is surfaced, how editorial moments get built into the feed, how trust signals appear next to a listing, and how a user goes from 'cute' to 'request' in under ten seconds.
Ensure the brand shows up in every state of the app, not just the marketing site (e.g., empty states, error states, email templates, push copy, micro-moments).
Design in Figma when exploration calls for it.
Work directly in code when execution calls for it, tuning spacing, adjusting copy, dialing in an easing curve, and shipping a small polish pass.
Partner closely with the cofounders and with engineering to contribute directly to the product, often without a handoff.
Use AI tools every day and with intention to accelerate exploration, generate variants, prototype in code, and scale output.
Shape how Pickle designs in the AI era.