Must be located in NYC (we are in office Monday - Thursday).Please apply by emailing (url removed) with VP of Operations in the subject line and include the following:Share 1-3 (max) bullets on why you think youre a standout applicant for this role.Share 1-2 (max) bullets summarizing an initiative youre most proud of and the impact it drove (we love metrics!)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. Were starting with peer-to-peer clothing and accessories and expanding into new categories.Were looking for a VP of Operations & Logistics Strategy to design and build the next chapter of Pickles operational backbone. Youll define the systems, partnerships, and pricing strategies that make our marketplace runtoday 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 OverviewAs VP of Operations & Logistics Strategy, youll own Pickles national logistics vision and its execution. Youll oversee all fulfillment, courier, and shipping networks; negotiate large-scale partnerships; and shape the unit economics that make our marketplace thrive. Youll experiment with new delivery methods and exchange channelsfrom neighborhood hub pilots to third-party repair and cleaning integrationsand ensure each is operationally sound and scalable.Youll 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.Requirements8+ years of experience leading operations, logistics, or marketplace strategy (fashion, DTC, or last-mile delivery a plus)Experience working with dual-sided marketplacesProven success building and scaling logistics networks across multiple cities or regionsDeep experience with courier pricing, rate negotiation, and cost optimizationDemonstrated ability to design operational systems and processes that scale efficientlyStrong analytical backgroundcomfortable with data modeling, forecasting, and decision-making using metricsExperience leading customer support or trust & safety functions within a consumer-facing platformExcellent collaborator, capable of working closely with Product, Eng, Marketing, and Community teamsEntrepreneurial and creative mindset; excited to design new, unconventional exchange modelsComfortable operating in a fast-paced, ambiguous startup environmentBonus: experience with 3PL integrations, hybrid logistics models, or localized operations playbooksResponsibilitiesDefine and lead Pickles long-term logistics and operations strategy across all marketsBuild and manage nationwide partnerships with courier networks, shippers, repair partners, and local facilitatorsDesign and implement scalable, cost-efficient delivery and return modelsNegotiate large-scale provider contracts and continually optimize pricing structuresLaunch pilots with new exchange methods (dry cleaners, community hubs, local ambassadors) and scale successful models nationallyDevelop operational data infrastructure and dashboards to track fulfillment speed, costs, and order success ratesPartner with Product and Engineering to automate key workflows and improve delivery reliabilityOversee Customer Experience and Trust & Safety alongside dedicated team leadsDrive operational KPIs and report performance metrics to leadership, balancing speed, cost, and customer delightMentor and develop the growing operations team; build a culture of ownership and creative problem solvingBenefitsCompetitive compensation and equityHealthcare (Medical, Dental, Vision)Take what you need paid time offMeal Pal credits to cover the cost of lunchStipend to help set up your desk and office environmentWork directly with the founders and executive teamProfessional coaching, training, and developmentGrow with the companyPickle credits for our employees, we love when the team uses Pickle!Fun team events and company partiesCompany offsitesOffice space in NYC