Director of Marketplace Health

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 Head of Marketplace Health to own and scale the supply side of the Pickle marketplace, and ensure marketplace health remains balanced across markets.

This role is responsible for building and maintaining high-quality, high-density supply across the platform. You’ll conduct rigorous analysis to identify supply gaps, then recruit and onboard high-potential closets, convert renters into lenders, and drive owner engagement — ensuring we have the right inventory, in the right places, at the right time.

Beyond supply growth, you’ll own marketplace health analysis. You’ll proactively dig into data to understand where markets are supply- or demand-constrained, identify patterns across cohorts and geographies, and take action accordingly. When markets are supply-constrained, you’ll own the path to rapidly increasing supply. When demand-constrained, you’ll partner cross-functionally with growth, product, and marketing teams to unlock demand.

This role also plays a key part in scaling new areas of the marketplace. As we expand into new categories or segments, you’ll be responsible for figuring out how to quickly build high-quality supply from 0 → hundreds → thousands of listings, and turning that into a repeatable playbook.

This is a highly strategic and executional role for someone who is deeply analytical, scrappy, and action-oriented — someone who can go from identifying a problem in the data to solving it in the real world, quickly.

Responsibilities

1. Supply Growth & Marketplace Health

• Own supply growth strategy across all markets

• Analyze marketplace data to identify trends, gaps, and performance drivers across markets and cohorts

• Define, track and surface marketplace health metrics

• Identify supply gaps by market, category, price point, and user segment

• Prioritize and execute against the most impactful supply opportunities, from recruiting high-quality closets to filling gaps quickly

• Surface data-driven insights and recommendations to improve marketplace liquidity and performance

• Partner cross-functionally to diagnose marketplace constraints and drive measurable improvements

2. Owner Activation & Engagement

• Drive renter → lender conversion

• Increase listing behavior among new and existing users

• Improve owner retention, reactivation, and engagement

• Identify and support high-performing lenders

• Identify and scale learnings

3. Scaling & Category Expansion

• Build playbooks for scaling supply across markets and categories

• Test and iterate on supply acquisition and onboarding strategies

• Identify and launch new supply verticals

• Take new categories from early traction → meaningful scale

4. Marketplace Insights & Balance

• Identify where markets are supply- and demand-side constrained

• Analyze cohorts (geo, behavior, category) to uncover gaps

• Design and run targeted tests to improve marketplace balance and growth

• Partner with product, growth, and lifecycle teams to translate insights into scalable initiatives

Who You Are

• 8+ years of experience in marketplaces, growth, strategy, or operations roles

• Experience working on two-sided marketplaces or supply-side growth

• Strong analytical mindset — you’re comfortable using data to identify gaps and opportunities

• Strategic and systems-oriented — you think in terms of levers, not just tasks

• Highly executional — you can move from strategy → implementation quickly

• Scrappy and resourceful — you can build supply from the ground up

• Strong cross-functional operator — you work well across product, growth, and market teams

• Deep ownership mindset — you treat marketplace health as your responsibility

• Comfortable in fast-paced, high-growth environments

Nice to Have

• Experience at companies like Whatnot, The RealReal, Depop, Uber, Airbnb, DoorDash, etc. (marketplace supply roles) during their early-stage growth days

• Experience working with sellers and developing systems that scale

• Experience in fashion, resale, or consumer marketplaces

• 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

• Team events, offsites, and strong IRL culture

• NYC office (Tribeca)