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Pickle is a peer-to-peer rental marketplace enabling consumers to rent high-quality items on-demand. The company has raised $20M and operates nationwide with 550K+ items listed, expanding beyond fashion into multiple categories.
As Head of Operations, you will design and build Pickle's fulfillment network from the ground up. This is a zero-to-one buildout of the systems, partnerships, and logistics infrastructure underlying every marketplace transaction. You'll own the complete operational strategy for a dual-sided marketplace where fulfillment decisions directly impact both supply-side trust and demand generation.
Key responsibilities include:
**Fulfillment Architecture**: Design and operate a multi-modal logistics network combining on-demand courier services, pickup/dropoff locations, and national/regional shipping. You'll negotiate volume-based contracts with partners like Uber, DoorDash, Roadie/UPS, and regional carriers.
**Neighborhood Network**: Build Pickle's local distribution infrastructure from scratch, establishing pickup/dropoff points at dry cleaners, boutiques, lockers, coffee shops, and similar venues. You may also lead assessment and potential deployment of Pickle's own transport fleet in select markets.
**Dynamic Pricing & Unit Economics**: Build and launch a dynamic pricing engine that aligns delivery costs with urgency, distance, and item value. Own the operations P&L including delivery margins, item protection, and insurance partnerships.
**Trust & Safety**: Partner with the customer experience lead to develop and scale the trust and safety framework, including item verification, dispute resolution, fraud prevention, and item protection insurance.
You'll work directly with founders and the executive team in a hands-on, on-the-ground role. This position requires deep marketplace expertise, analytical rigor in unit economics modeling, and proven success building asset-light, partner-operated networks at scale.
