Head of Operations

Must be located in NYC (we are in office Monday - Thursday). Please apply by emailing recruiting@shoponpickle.com with “Head of Operations” in the subject line and include the following:

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

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 seasoned, strategic, and scrappy Head of Operations to lead the team responsible for delivering the best possible experience to both renters and lenders—from seamless deliveries to trust-worthy interactions. You’ll own 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:

As Head of Operations, you’ll be responsible for designing and executing the end-to-end operational engine that powers our marketplace. You will oversee logistics (courier and shipping), customer support, and trust & safety policies. You’ll identify weak points in our order flow, refine our delivery model, and ensure every rental feels magical—for both the renter and the lender.

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

• 6+ years of experience in marketplace, e-commerce, or logistics operations (fashion, DTC, or mobility a plus)
• Experience owning courier logistics and/or shipping infrastructure, ideally with direct provider negotiations
• Proven ability to design systems that scale while maintaining great customer experience
• Analytical mindset; comfortable diving into delivery failure rates, NPS, or operational KPIs
• Experience managing customer support or trust teams (bonus if you’ve helped scale them)
• Excellent cross-functional collaborator, able to work with Product, Eng, Community, and Marketing
• Empathetic and user-obsessed; you care about how people feel when they rent on Pickle
• Strong analytical and problem-solving skills—able to make data-driven decisions that balance cost, speed, and user experience.
• Experience with last-mile delivery and in-person exchange logistics.
• Comfortable working in a fast-moving, dynamic startup environment.
• Analytical/technical skills such as SQL, dashboarding, or other forms of data analysis
• Bonus: experience launching or scaling city-level operations or fulfillment centers

Responsibilities

• Lead and scale operations across courier pick-up/drop-off, shipping, returns, and delivery reliability
• Manage relationships and negotiate rates with 3rd party logistics and courier providers
• Drive pricing strategy for all delivery options—including real-time optimizations based on cost, margin, and experience
• Analyze and address the drivers of failed orders, late deliveries, or inventory mismanagement
• Build infrastructure to detect and prevent renter/lender behaviors that could disrupt delivery success
• Design scalable delivery solutions for new markets, accounting for local constraints and user behaviors
• Oversee the customer experience function, ensuring timely, friendly, and effective support
• Develop and enforce Trust & Safety policies that protect both renters and lenders while encouraging peer-to-peer participation
• Collaborate cross-functionally to inform product features that reduce ops burden or customer friction
• Report on operational performance, logistics costs, and support team KPIs; define and drive improvement targets

• Competitive compensation and equity
• Healthcare (Medical, Dental, Vision)
• Take what you need paid time off
• Meal Pal 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