Community Programs Lead

About PicklePickle is a peer-to-peer rental marketplace unlocking the value of the billions of underutilized items sitting in consumers’ closets. We make it easy to rent high-quality items exactly when you need them — with fast, convenient fulfillment and an on-demand experience that’s as seamless as shopping.We’re building a new kind of commerce layer: one powered by dynamic local supply, where access is more convenient than ownership. Pickle is now live nationwide and scaling rapidly in key markets including NYC, LA, Miami, Dallas, Austin, Chicago, with 400K+ items listed for rent.Backed by our Series A (FirstMark, Craft), we’re moving fast and building the future of access-driven shopping.About The RoleWe’re hiring a Community Programs Lead to own and scale Pickle’s Growth Fellow and Brand Ambassador ecosystem nationwide (and beyond!).This role is responsible for turning our community into a consistent, scalable growth engine. You’ll define how our programs are structured, manage cohorts across markets, and ensure we’re driving high-quality activations, referrals, and real marketplace activity.This is a highly operational, people-heavy role — ideal for someone who loves building systems, managing distributed communities, connecting and motivating program members on a daily basis, and driving measurable outcomes through people.ResponsibilitiesProgram Strategy & StructureDefine and evolve the structure, incentives, and expectations for Growth Fellows and Brand AmbassadorsBuild scalable systems to support program growth across marketsIdentify opportunities to improve performance and drive efficiencyProgram Ownership & ExecutionOwn execution of:Growth Fellows (non-undergrad: city, MBA, etc.)Brand Ambassador programManage strategy & oversee execution of College Growth Fellow programManage full cohorts across multiple marketsDrive consistent, high-quality activations across marketsEnsure Fellows and Ambassadors are activating weekly in-market (events, referrals, etcLead onboarding, training, and weekly communication (calls, check-ins, performance tracking)Systems, Tracking & OptimizationTrack program performance across key metrics and marketsMonitor cohort engagement, output, and retentionContinuously refine playbooks for onboarding, activations, engagementIdentify operational improvements, opportunities to automate and build repeatable systems to scale what worksEnsure alignment between community programs and broader growth and brand initiativesWho You Are4–7 years of experience in community, programs, operations, or growth rolesExperience managing ambassador programs, campus reps, or distributed communities / programsHighly organized — you can manage multiple cohorts, markets, and timelines simultaneously without dropping the ballStrong operator — you build structure, systems, and accountability while continuing to execute; you’ve built scalable systems with measurable resultsPeople-oriented — you love to hop on a call, connect with people and you’re great at motivating and managing communitiesData-driven — you track performance and optimize based on resultsScrappy and resourceful — you can drive results (and motivate others to drive results) without large budgetsStrong communicator — clear, consistent, and able to manage many stakeholdersComfortable in fast-paced, high-growth environmentsNice to HaveExperience with marketplace or consumer app growthExperience running community-led events or activationsBackground in fashion, creators, or community-driven brandsEarly stage startup experienceActive Pickle user or strong familiarity with the productBenefitsCompetitive compensation + equityHealthcare (Medical, Dental, Vision)Take what you need paid time offMealPal credits for lunchStipend to set up your workspaceWork directly with founders and leadershipProfessional development + coachingPickle credits (yes, we want you using the product!)Team events, offsites, and strong IRL cultureNYC office (Tribeca)Compensation Range: $130K - $150K