About Pickle

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. Pickle is now live nationwide and scaling rapidly. Our marketplace already features 400K+ items, and we’re just getting started. We’re excited to extend our vision beyond fashion into every category.

We've raised $20M to date from FirstMark, Craft, Burst Capital, FJ Labs, and others.

About This Role

The Head of Operations will design and own the physical infrastructure of Pickle's marketplace. This is a zero-to-one buildout: the systems, networks, and partnerships that sit underneath every transaction don't fully exist yet. You will build them.

We're looking for someone who lives and breathes marketplaces. Who instinctively understands that every operational decision has two sides, and that the right fulfillment network doesn't just move items, it builds supply-side trust and unlocks demand. You've seen what happens when liquidity meets logistics friction, and you know how to fix it.

This isn't a role for someone who optimizes existing systems. It's for someone who has stared at a blank whiteboard and built the network from scratch. Who gets excited by the unit economics before the infrastructure exists, and who sees a neighborhood dry cleaner not as a vendor but as a distribution node.

What You'll Own

Fulfillment Architecture

• Design and operate a logistics network that includes: on-demand courier, pick up/drop off locations, and national/regional shipping.

• Negotiate volume-based contracts with courier partners (Uber, DoorDash, Roadie/UPS, regional carriers).

Drop Off Locations

• Build Pickle's neighborhood-level network from scratch: drop-off/pickup points across dry cleaners, boutiques, lockers, coffee shops.

• Procure, brand, and deploy Pickle's own transport fleet.

Dynamic Pricing & Unit Economics

• Build and launch a dynamic pricing engine that aligns delivery cost with urgency, distance, and item value.

• Own the ops P&L: delivery margin, item protection/insurance, etc.

Trust & Safety

• Work with our CX lead to build and scale the full trust and safety framework: item verification, dispute resolution, fraud prevention, and item protection/insurance partnerships.

Requirements

• 8+ years in operations, logistics, or marketplace strategy, with direct experience building and scaling multi-market logistics networks

• Proven track record with asset-light, partner-operated networks (not warehouse ownership. We're building on aligned incentives, not fixed costs)

• Experience with dual-sided marketplaces or peer-to-peer platforms; understands supply-side and demand-side dynamics simultaneously

• Analytically sharp: you build unit economics models before you sign contracts and own the P&L

• Track record of reducing cost per transaction meaningfully: through carrier negotiation, routing optimization, or network design

• NYC-based; this is a hands-on, on-the-ground role.

Benefits

• Competitive compensation and equity

• Healthcare (Medical, Dental, Vision)

• Take what you need paid time off

• Meal Pal credits to cover the cost of lunch

• Stipend to help set up your desk and office environment

• Work directly with the founders and executive team

• Professional coaching, training, and development

• Grow with the company

• Pickle credits for our employees, we love when the team uses Pickle!

• Fun team events and company parties

• Company offsites

• Office space in NYC