Manager, Strategy and Operations

Must be located In NYC (we are in office Monday-Thursday). Please apply by emailing recruiting@shoponpickle.com with “Manager, Strategy and Operations” in the Subject Line and include the following:

• 1-3 (max) bullets on why you think you’re a standout applicant for this role
• 1-2 (max) bullets summarizing an initiative you’re most proud of and the impact it drove (we love metrics!)
• Your Pickle username and your favorite app feature
• Your resume

Pickle is a rental marketplace that aims to monetize the billions of underutilized assets sitting in consumers’ closets and brands’ inventory. Users can easily tap into shared closets within their community through flexible and/or on-demand delivery options. Our goal is to provide affordable and convenient access to quality items exactly when our users need them. We are starting with P2P clothing/accessories and expanding to other categories.

We’re looking for a strategic and scrappy Strategy and Ops Manager to join the team responsible for delivering the best possible experience to both renters and lenders—from seamless deliveries to trust-worthy interactions. You’ll focus on the systems, strategy, and execution behind how orders get fulfilled, how problems get resolved, and how we scale logistics and support into new markets.

Role Overview

Reporting directly to the Head of Operations, you will work on defining and executing the end-to-end operational engine that powers our marketplace. You will focus on logistics (courier and shipping), optimizing operations for Pickle’s NYC brick and mortar store, customer experience, and trust & safety. You’ll identify weak points in our order flow, refine our delivery model, and work to ensure every rental feels magical—for both the renter and the lender.

You will work closely with the Product, Engineering, Community, and Marketing teams to ensure local nuances and platform-wide needs are met with scalable solutions.

Requirements

• 5+ years of experience in marketplace, e-commerce, or last-mile delivery logistics operations (fashion, DTC, or mobility a plus)
• Strong analytical and problem-solving skills—able to make data-driven decisions that balance cost, speed, and user experience
• Ability to design systems that scale while maintaining great customer experience
• Excellent cross-functional collaborator; able to work with Product, Engineering, Community, and Marketing
• Empathetic and user-obsessed; you care about how people feel when they rent on Pickle
• Comfortable working in a fast-moving, dynamic startup environment

Responsibilities

• Focus on scaling and optimizing operations across courier pick-up/drop-off and shipping
• Analyze and address drivers of imperfect orders, such as cancellations, late pickup/delivery, etc.
• Report on operational performance, logistics costs, and support team KPIs; help define and drive improvement targets
• Consider pricing strategy for all delivery options
• Build upon and refine infrastructure to detect and prevent renter/lender behaviors that could disrupt the lending/rental experience
• Identify opportunity areas and work the Store team to continuously improve the operations of Pickle’s NYC brick and mortar store
• Work closely with the customer experience function to ensure quick and correct, friendly, cost-effective support
• Develop and monitor Trust & Safety product features, policies, and processes that protect both renters and lenders while encouraging peer-to-peer participation
• Collaborate cross-functionally to inform product features that reduce ops burden and/or customer friction

Benefits

• Competitive compensation and equity
• Healthcare (Medical, Dental, Vision)
• Take what you need paid time off
• MealPal credits to cover the cost of lunch
• Stipend to help set up your desk and office environment
• Work directly with the founders and executive team
• Professional coaching, training, and development
• Grow with the company
• Pickle credits for our employees, we love when the team uses Pickle!
• Fun team events and company parties
• Company offsites
• Office space in NYC