About The Company

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.

Role Overview

As Head of Engineering, you’ll oversee the development of our mobile, web, and backend platforms. You’ll partner closely with Product, Design, and Operations to build features that support renter and lender growth, ensure marketplace health, and unlock new types of logistics and community experiences.

You’ll be responsible for the technical vision, architectural decisions, engineering execution, and team building needed to grow Pickle into a best-in-class consumer marketplace.

Requirements

• 10+ years of experience in software engineering, with at least 4+ years managing teams

• Desire to be a “player/coach” by hiring and managing engineers as well as contributing to the code

• Experience building and scaling consumer-facing platforms or marketplaces (bonus if peer-to-peer)

• Strong engineering experience, ideally with React Native, Next.js, and AWS developer services

• Deep understanding of full-stack architecture, CI/CD practices, and performance optimization

• Passionate about great UX and clean code

• A strategic mindset: you can balance product velocity with long-term tech investments

• Experience working cross-functionally with product, design, and operations

• Comfortable in a fast-paced, lean, collaborative environment

• Bonus: experience with logistics, payments, or trust & safety engineering domains

Key Responsibilities:

• Own Pickle’s technical roadmap, ensuring the platform is scalable, secure, and performant

• Manage and grow a high-performing engineering team; mentor engineers across levels

• Contribute to frontend and backend codebases, review pull requests, and set up engineering tooling and automation

• Partner with Product and Design to define and deliver features that improve user experience and drive marketplace outcomes (e.g. conversion, retention, liquidity)

• Own technical metrics (e.g. uptime, API response times, crash rates, etc.) and monitoring and observability tooling

• Architect backend systems to support logistics, trust and safety, user growth, and marketplace matching

• Ensure the platform supports data-informed decision-making through clean analytics integrations

• Collaborate with Growth, Ops, and Community teams to improve delivery flows, messaging systems, and onboarding experiences

• Build scalable infrastructure to support multi-market complexity and local nuance

• Evaluate and own key technical partnerships, tooling, and development frameworks

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