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Head of Operations

shoponpickleNew York City
On-site Full-time

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Experience Level

Senior Level Manager

Qualifications

RequirementsA minimum of 8 years of experience in operations, logistics, or marketplace strategy (experience in fashion, DTC, or last-mile delivery is a plus). Experience in managing dual-sided marketplaces. Demonstrated success in building and scaling logistics networks across multiple cities or regions. Extensive experience in negotiating partnerships and executing logistics strategies.

About the job

About Pickle

Pickle is an innovative peer-to-peer rental marketplace that transforms the potential of underutilized items resting in consumers’ closets into accessible rental opportunities. We streamline the process of renting high-quality items precisely when you need them, offering fast fulfillment and a seamless shopping experience.

We are pioneering a new commerce model, fueled by dynamic local supply, ensuring convenient access to various goods. Currently, Pickle is active nationwide and rapidly expanding in key markets such as New York City, Los Angeles, and Miami. Our platform boasts a diverse selection of over 300,000 items available for rent, and we are just getting started.

What sets Pickle apart is our unique blend of peer-to-peer inventory, unmatched convenience (under 2 days nationwide and under 2 hours locally), and a flexible on-demand model with no subscriptions. Users can rent items whenever they desire. Following our Series A funding secured in early 2025 from FirstMark and Craft, we are poised for rapid growth as we redefine access-driven shopping.

About This Role

We are on the lookout for a Head of Operations to architect and develop the next phase of Pickle’s operational framework. You will be responsible for defining systems, partnerships, and pricing strategies essential for our marketplace’s success, both now and in the future. This role encompasses everything from last-mile delivery pricing to innovative exchange models such as dry cleaner pickups, local hubs, or trusted community return partners.

As the Head of Operations, you will lead Pickle’s national logistics vision and ensure effective execution. Your responsibilities will include overseeing fulfillment, courier, and shipping networks, negotiating significant partnerships, and shaping the unit economics that drive our marketplace’s success. You will explore new delivery methods and exchange channels, from neighborhood hub pilots to collaborations with third-party repair and cleaning services, ensuring that each is operationally robust and scalable.

You will also manage and mentor a growing team in operations while collaborating cross-functionally with Product and Data to develop the tools and insights necessary for operational excellence.

About shoponpickle

Pickle is an exciting and expanding rental marketplace that provides consumers with an easy way to access high-quality items for rent. Our mission is to unlock the value of underutilized goods through a convenient and efficient platform, redefining the rental experience.

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