VP of Operations

Must be located in NYC (we are in office Monday - Thursday).
Please apply by emailing with "VP 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 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.

This is a highly strategic and executional role for a builder who wants to rethink what it means to move physical goods in a peer-to-peer world. You'll collaborate closely with Product, Community, and Marketing to transform operational innovation into an unforgettable user experience.

*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, including the Manager of Strategy & Ops and Customer Experience Lead, 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