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. Pickle is now live nationwide and scaling rapidly in key local markets including NYC, LA, and Miami. Our marketplace already features 300K+ items listed for rent, and we’re just getting started.

What makes Pickle different is the combination of incredible peer-to-peer inventory, industry-leading convenience (under 2 days nationwide and under 2 hours locally), and an on-demand model with no subscriptions — users rent what they want, when they want it. Backed by our Series A funding raised in early 2025 from FirstMark and Craft, we’re scaling quickly and building the future of access-driven shopping.

About The Role

We are moving past the "early startup" phase of outsourced bookkeeping and ad-hoc modeling. We need a leader to own the Financial Truth of the company. You will take full ownership of accounting operations, build a robust FP&A engine to guide executive decision-making, and ensure we are compliant and audit-ready as we scale toward Series B and beyond.

Responsibilities

FP&A and Strategic Planning

• The Operating Model: Own the company’s master financial model. You will provide the Founders and Board with a clear, live view of cash runway, burn rate, and hiring capacity.

• Unit Economics: Deep-dive analysis into marketplace metrics. You will obsess over CAC, LTV, Contribution Margin, and Take Rate, identifying levers to improve profitability.

• Fundraising Strategy: Partner with the CEO to prepare for Series B. You will craft the financial narrative, build the data room, and manage due diligence requests.

Financial Operations & Controllership

• Own the Close: Manage the monthly, quarterly, and annual close process. You will transition us from outsourced providers to a rigorous in-house process, ensuring GAAP compliance and timely reporting.

• Marketplace Compliance: Manage the complexity of a two-sided marketplace. This includes overseeing Marketplace Facilitator Tax laws (sales tax nexus across 50 states), 1099-K issuance for sellers, and escrow management.

• Audit & Treasury: Lead all future audit preparations. Manage cash flow, AP/AR, and optimize our treasury strategy to ensure liquidity and capital preservation.

• Spend Management: Implement and oversee spend control systems (e.g., Ramp, Brex, Airbase). You will enforce budget discipline across departments without slowing down execution.

Financial Systems & Data Integrity

• Systems Design: Select and implement the right financial tech stack (ERP, Billing, Reporting) that scales with us.

• Product Collaboration: Collaborate with the Engineering team to ensure our platform’s internal ledger accurately captures the data Finance needs. You act as the "Quality Assurance" for financial data, ensuring that what happens in the app matches what lands in the bank.

Requirements

• 7+ Years Experience: Operational finance leadership in a start-up and/or high-growth environment (Big 4 Accounting, IB, Private Equity, Corporate Development). Experience with financial reporting and a thorough understanding of accounting fundamentals.

• Marketplace Experience: Preferably experience with marketplaces. You understand the specific accounting nuances of GMV vs. Net Revenue, Contribution Profit, liability management, and high-volume transaction reconciliation.

• Operational Excellence: You are a "doer." You are willing to dig into the GL to reconcile a discrepancy, but you also have the presence to present the Q3 forecast to the Board.

• Data Fluency: You are comfortable with modern data tools. You understand how to bridge the gap between raw database exports and financial statements.

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