Head of Operations

Pickle; New York (NY); On-site; USD 58,000 - 160,000; Full time

Job summary

An innovative rental marketplace is seeking a strategic Head of Operations to enhance the user experience for both renters and lenders. This role involves overseeing logistics, customer support, and trust & safety policies, ensuring seamless deliveries and reliable interactions. You will collaborate with cross-functional teams to refine operational systems and scale logistics into new markets. If you thrive in fast-paced environments and have a passion for optimizing processes, this position offers a unique opportunity to make a significant impact in a growing company.

Benefits

Competitive compensation and equity

Healthcare (Medical, Dental, Vision)

Flexible paid time off

Meal Pal credits

Desk setup stipend

Professional coaching and development

Company offsites

Fun team events

Pickle credits for employees

Qualifications

• 6+ years of experience in marketplace, e-commerce, or logistics operations.
• Experience managing customer support or trust teams.
• Strong analytical and problem-solving skills.

Responsibilities

• Lead and scale operations across courier pick-up/drop-off and shipping.
• Manage relationships and negotiate rates with logistics providers.
• Design scalable delivery solutions for new markets.

Skills

Marketplace Operations

Logistics Management

Customer Support

Analytical Skills

Problem-Solving

Education

Bachelor's Degree

Master's Degree (preferred)

Tools

SQL

Data Analysis Tools

Job description

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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.

Requirements

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

Benefits

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

Seniority level

• Seniority level

  Executive

Employment type

• Employment type

  Full-time

Job function

• Job function

  Management and Manufacturing

• Industries

  Truck Transportation and Civil Engineering

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