Pickle · 2 hours ago
Senior Fullstack Engineer (Payments Architecture)
New York, NY
Full-time
Onsite
Senior Level
$180K/yr - $220K/yr
5+ years expPickle is a peer-to-peer rental marketplace focused on unlocking the value of underutilized items. They are seeking a Senior Fullstack Engineer to build the financial engine of their platform, focusing on creating a robust payments architecture and internal ledger system.
ApparelFashionMarketplacePeer to PeerRental
Responsibilities
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
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
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
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
Qualification
Required
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
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
Preferred
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
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
Company
Pickle
Pickle is a peer-to-peer clothing rental marketplace that allows users to rent trendy outfits from their local community.
11-50 employees
H1B Sponsorship
Pickle has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (1)
Funding
Current Stage
Early StageTotal Funding
$20M2025-03-12Series A· $12M
2023-10-11Seed· $8M
Leadership Team
Brian McMahon
Chief Executive Officer
Julia O'Mara
Co-Founder & COO
Recent News
Daring Fireball
2026-01-06
2026-01-05
2026-01-05
Company data provided by crunchbase