Head of Ops
About Pickle
Pickle is a peer-to-peer rental marketplace that aims to unlock the value of underutilized items by making it easy to rent high-quality items on-demand. Founded with a mission to build a new kind of commerce layer powered by dynamic local supply, Pickle is now live nationwide and growing rapidly. With 550K+ items available, Pickle continues to expand its offerings across various categories.
We have raised $20M to date from leading investors including FirstMark, Craft, Burst Capital, and FJ Labs. Our vision extends beyond fashion into every product category, driven by a passionate team committed to innovation and customer satisfaction.
About This Role
The Head of Ops will be responsible for designing and operating the fulfillment network of Pickle's marketplace. This role involves building from scratch the systems, networks, and partnerships that support every transaction. The ideal candidate must have a deep understanding of marketplaces and the ability to see beyond traditional logistics constraints.
Design and operate a logistics network that includes on-demand couriers, pickup/drop-off locations, and national/regional shipping.
Negotiate volume-based contracts with courier partners such as Uber, DoorDash, Roadie/UPS, and regional carriers.
Build Pickle's neighborhood-level network from scratch, including drop-off/pickup points at dry cleaners, boutiques, lockers, and coffee shops.
Lead the procurement, branding, and deployment of Pickle's own transport fleet in select markets.
Develop and launch a dynamic pricing engine that aligns delivery costs with urgency, distance, and item value.
Own the operations P&L, focusing on delivery margins, item protection/insurance, and other financial metrics.
Work with the Customer Experience lead to build and scale the trust and safety framework, including item verification, dispute resolution, fraud prevention, and insurance partnerships.
Requirements
8+ years of experience in operations, logistics, or marketplace strategy, with a focus on building and scaling multi-market first-mile and last-mile logistics networks.
Experience with asset-light, partner-operated networks rather than warehouse ownership; a focus on aligned incentives and flexible costs.
Understanding of dual-sided marketplaces and the interplay between supply-side and demand-side dynamics.
An analytically sharp approach to problem-solving, building unit economics models before signing contracts and owning the P&L.
A proven track record of reducing cost per transaction through carrier negotiation, routing optimization, or network design.
NYC-based and in-office role; hands-on, on-the-ground responsibilities.
Benefits
Competitive compensation and equity
Healthcare benefits (Medical, Dental, Vision)
Take what you need paid time off
Meal Pal credits to cover lunch expenses
Stipend for setting up your desk and office environment
Work directly with the founders and executive team
Professional coaching, training, and development opportunities
Growth within the company
Pickle credits for employees
Compensation Range
$200K - $250K