Community Programs Lead

About Pickle

Pickle 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 Role

We’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.

Responsibilities

Program Strategy & Structure

• Define and evolve the structure, incentives, and expectations for Growth Fellows and Brand Ambassadors

• Build scalable systems to support program growth across markets

• Identify opportunities to improve performance and drive efficiency

Program Ownership & Execution

• Own execution of:

  • Growth Fellows (non-undergrad: city, MBA, etc.)

  • Brand Ambassador program

• Manage strategy & oversee execution of College Growth Fellow program

• Manage full cohorts across multiple markets

• Drive consistent, high-quality activations across markets

• Ensure Fellows and Ambassadors are activating weekly in-market (events, referrals, etc

• Lead onboarding, training, and weekly communication (calls, check-ins, performance tracking)

Systems, Tracking & Optimization

• Track program performance across key metrics and markets

• Monitor cohort engagement, output, and retention

• Continuously refine playbooks for onboarding, activations, engagement

• Identify operational improvements, opportunities to automate and build repeatable systems to scale what works

• Ensure alignment between community programs and broader growth and brand initiatives

Who You Are

• 4–7 years of experience in community, programs, operations, or growth roles

• Experience managing ambassador programs, campus reps, or distributed communities / programs

• Highly organized — you can manage multiple cohorts, markets, and timelines simultaneously without dropping the ball

• Strong operator — you build structure, systems, and accountability while continuing to execute; you’ve built scalable systems with measurable results

• People-oriented — you love to hop on a call, connect with people and you’re great at motivating and managing communities

• Data-driven — you track performance and optimize based on results

• Scrappy and resourceful — you can drive results (and motivate others to drive results) without large budgets

• Strong communicator — clear, consistent, and able to manage many stakeholders

• Comfortable in fast-paced, high-growth environments

Nice to Have

• Experience with marketplace or consumer app growth

• Experience running community-led events or activations

• Background in fashion, creators, or community-driven brands

• Early stage startup experience

• Active Pickle user or strong familiarity with the product

Benefits

• Competitive compensation + equity

• Healthcare (Medical, Dental, Vision)

• Take what you need paid time off

• MealPal credits for lunch

• Stipend to set up your workspace

• Work directly with founders and leadership

• Professional development + coaching

• Pickle credits (yes, we want you using the product!)

• Team events, offsites, and strong IRL culture

• NYC office (Tribeca)