Must be located in NYC (we are in office Monday - Thursday).

Please apply by emailing recruiting@shoponpickle.com with "VP of Operations" in the subject line and include the following:

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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 on-demand delivery options. Our goal is to provide affordable and convenient access to quality items exactly when our users need them. We're starting with peer-to-peer clothing and accessories and expanding into new categories.

We're looking for a VP of Operations & Logistics Strategy to design and build the next chapter of Pickle's operational backbone. You'll define the systems, partnerships, and pricing strategies that make our marketplace run—today and at scale. This person will own everything from last-mile delivery pricing to creative new exchange models like dry cleaner pickups, local hubs, or trusted community return partners.

Role Overview:

As VP of Operations & Logistics Strategy, you'll own Pickle's national logistics vision and its execution. You'll oversee all fulfillment, courier, and shipping networks; negotiate large-scale partnerships; and shape the unit economics that make our marketplace thrive. You'll experiment with new delivery methods and exchange channels—from neighborhood hub pilots to third-party repair and cleaning integrations—and ensure each is operationally sound and scalable.

You'll manage and mentor a growing operations team while working cross-functionally with Product and Data to build the tools and insights that power our operational excellence.

Requirements

8+ years of experience leading operations, logistics, or marketplace strategy (fashion, DTC, or last-mile delivery a plus)
Proven success building and scaling logistics networks across multiple cities or regions
Deep experience with courier pricing, rate negotiation, and cost optimization
Demonstrated ability to design operational systems and processes that scale efficiently
Strong analytical background—comfortable with data modeling, forecasting, and decision-making using metrics
Experience leading customer support or trust & safety functions within a consumer-facing platform
Excellent collaborator, capable of working closely with Product, Eng, Marketing, and Community teams
Entrepreneurial and creative mindset; excited to design new, unconventional exchange models
Comfortable operating in a fast-paced, ambiguous startup environment
Bonus: experience with 3PL integrations, hybrid logistics models, or localized operations playbooks

Responsibilities

Define and lead Pickle's long-term logistics and operations strategy across all markets
Build and manage nationwide partnerships with courier networks, shippers, repair partners, and local facilitators
Design and implement scalable, cost-efficient delivery and return models
Negotiate large-scale provider contracts and continually optimize pricing structures
Launch pilots with new exchange methods (dry cleaners, community hubs, local ambassadors) and scale successful models nationally
Develop operational data infrastructure and dashboards to track fulfillment speed, costs, and order success rates
Partner with Product and Engineering to automate key workflows and improve delivery reliability
Oversee Customer Experience and Trust & Safety alongside dedicated team leads
Drive operational KPIs and report performance metrics to leadership, balancing speed, cost, and customer delight
Mentor and develop the growing operations team; build a culture of ownership and creative problem solving

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

Pickle

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VP of Operations & Logistics Strategy