Head of Operations

About Pickle

Pickle is a peer-to-peer rental marketplace unlocking the value of 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 as seamless as shopping. We're building a new kind of commerce layer powered by dynamic local supply, where access is more convenient than ever.

Pickle is now live nationwide and scaling rapidly. Our marketplace already features 400K+ items, and we're expanding beyond fashion into every category. We've raised $20M to date from leading investors including FirstMark, Craft, Burst Capital, and FJ Labs.

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 from the ground up.

We're looking for someone who lives and breathes marketplaces. You instinctively understand 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 role isn't 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 unit economics before 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 including on-demand courier, pick-up/drop-off locations, and national/regional shipping
• Negotiate volume-based contracts with courier partners such as Uber, DoorDash, Roadie/UPS, and regional carriers

Drop-Off Locations

• Build Pickle's neighborhood-level network from scratch: drop-off/pickup points across dry cleaners, boutiques, lockers, and 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, and profitability metrics

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

Ideal candidates have 5+ years building marketplace operations from scratch, deep experience in logistics and fulfillment networks, and a track record of scaling unit economics. You should have strong relationships with logistics partners, comfort with ambiguity, and the ability to move fast while thinking systematically about long-term infrastructure. Experience in peer-to-peer or rental marketplaces, understanding of dynamic pricing systems, and proven success launching trust and safety programs are valuable assets.

💰 Compensation not publicly listed. Market estimate for similar roles: from $80K, varying by experience and location.