Director of Operations & Logistics

Pickle•New York, NY

8d•$185,000 - $240,000•Onsite

About The Position

Pickle is a peer-to-peer rental marketplace for renting underutilized consumer items, currently live nationwide and scaling rapidly. The Director of Operations & Logistics will design and own the marketplace’s fulfillment network in a zero-to-one role, building the systems, networks, and partnerships that support transactions. Pickle primarily uses third-party fulfillment partners and does not own or handle inventory. The role calls for a marketplace-focused operator who understands how fulfillment choices affect both supply-side trust and customer demand. The director will build a network spanning on-demand couriers, pickup and drop-off locations, and national or regional shipping. They will develop dynamic delivery pricing, own operating economics, and establish neighborhood pickup and drop-off points. The role is based in NYC, is in-office, and is hands-on and on the ground.

Requirements

At least 8 years of experience in operations, logistics, or marketplace strategy.
Direct experience building and scaling multi-market first-mile and last-mile logistics networks.
Proven experience with asset-light, partner-operated networks rather than warehouse ownership.
Experience with dual-sided marketplaces or peer-to-peer platforms and understanding of supply-side and demand-side dynamics.
Strong analytical skills, including building unit economics models before signing contracts and owning a P&L.
A track record of meaningfully reducing cost per transaction through carrier negotiation, routing optimization, or network design.
Must be based in NYC and work in-office.

Responsibilities

Design and operate a fulfillment network covering on-demand couriers, pickup and drop-off locations, and national or regional shipping.
Negotiate volume-based contracts with courier partners, including Uber, DoorDash, Roadie/UPS, and regional carriers.
Build and launch a dynamic pricing engine that aligns delivery costs with urgency, distance, and item value.
Own the operations P&L, including delivery margin and item protection or insurance.
Build a neighborhood pickup and drop-off network from scratch, including locations at dry cleaners, boutiques, lockers, and coffee shops.
Assess the opportunity and potentially lead procurement, branding, and deployment of Pickle's own transport fleet in select markets.
Reduce cost per transaction through carrier negotiation, routing optimization, or network design.