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 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

Your mission is to build the financial engine of our platform.

This role owns the architecture behind how money moves through our system. While we use Stripe today (Payments, Connect, and Tax), the system you design must be vendor-agnostic, auditable, and correct by construction. Stripe should be treated as a utility, not a source of truth.

You will design an internal ledger and payment services that ensure every cent is tracked, reconciled, and reportable — independent of any third-party dashboard. This is a high-impact, high-trust role at the core of our marketplace.

If you enjoy building rigorous systems, thinking in invariants, and owning complex financial domains end-to-end, this role is for you.

Key Responsibilities

1. Modular Payments Architecture

• Design and own a dedicated Payments Service that abstracts the underlying provider (Stripe).

• Apply architectural patterns (Adapter, Facade) to isolate provider-specific logic from core business logic.

• Ensure the system can support future processors or redundancy without requiring a platform rewrite.

• Architect complex marketplace money flows, including:

  • Peer-to-peer payouts

  • Platform commissions and fees

  • Hold periods and delayed settlement

• Build resilient systems that handle retries, network failures, and webhook delivery safely.

• Ensure all payment operations are idempotent and fault-tolerant.

2. Internal Ledger & Financial Data Modeling

• Design and implement an internal ledger system (double-entry bookkeeping or rigid transaction log) in Postgres.

• Ensure the database — not Stripe — is the system of record for balances, payouts, and transaction history.

• Model wallets, transactions, ledger entries, and settlements with strict constraints and invariants.

• Build reconciliation processes that automatically compare internal state with Stripe settlement data.

• Structure financial data to support:

  • P&L reporting

  • Payout schedules

  • Tax reporting and audits

3. Full-Stack Payments Implementation

• Build type-safe tRPC APIs for checkout, wallet management, payouts, and payment method management.

• Collaborate with frontend engineers to integrate payments into the product in a way that is transparent and trustworthy for users.

• Hide backend complexity behind clean APIs and intuitive UI flows.

• Ensure payment-related user experiences are accurate, predictable, and easy to reason about.

4. Codebase & Domain Ownership

• Own the payments domain within our Turborepo (or similar).

• Define strict boundaries between Payments, Core Business Logic, and UI layers.

• Ensure payment logic is isolated, testable, and resistant to accidental misuse.

• Set standards for how high-stakes systems are built, reviewed, and evolved.

Required Qualifications

• 5+ years of professional engineering experience, with significant ownership of payment systems or financial data.

• Deep experience designing and operating payment infrastructure in production.

• Strong understanding of service decoupling and interface-driven design.

• Expert-level SQL knowledge, including transaction isolation levels and data integrity guarantees.

• Experience building ACID-compliant systems where correctness matters more than convenience.

• Strong TypeScript skills, including generics and strict typing for high-risk domains.

• Experience organizing complex domains within a monorepo or service-oriented architecture.

Stripe-Specific Experience

• Deep hands-on experience with Stripe Connect.

• Experience handling marketplace payouts, refunds, disputes, and settlement timing.

• Familiarity with Stripe webhooks, idempotency keys, and failure modes.

• Experience integrating Stripe Tax or similar tax calculation systems.

Nice to Have

• Experience designing double-entry accounting systems or financial ledgers.

• Experience with multiple payment processors (e.g., Adyen, Braintree).

• Experience supporting audits or financial reporting pipelines.

• Familiarity with marketplace compliance and tax considerations.

First 10 Weeks: What You’ll Ship

• Ledger schema: Design and implement the Postgres schema for Wallets, Transactions, and Ledger Entries.

• Payment abstraction layer: Define TypeScript interfaces that isolate Stripe-specific logic behind a clean Payments Service.

• Reconciliation jobs: Build automated processes to validate internal balances against Stripe settlement data.

Our Desired Stack

• Core: Node.js, TypeScript, tRPC

• Payments: Stripe Payments, Stripe Connect, Stripe Tax

• Database: Postgres (Supabase), Drizzle ORM

• Architecture: Turborepo, Modular Monolith

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