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Head of Engineering

2 weeks ago

New York, New York, United States Pickle Full time

Must be located in NYC (we are in office Monday - Thursday). Please apply by emailing  with "Head of Engineering" in the subject line and include the following:

  • Share 1-3 (max) bullets on why you think you're a standout applicant for this role.
  • Share 1-2 (max) bullets summarizing an initiative you're most proud of and the impact it drove (we love metrics)
  • Which Pickle feature would you be most excited to work on if you got the job tomorrow?

Pickle is a rental marketplace that aims to monetize the billions of underutilized assets sitting in consumers closets and brands inventory. Users can easily tap into shared closets within their community through flexible and/or on-demand delivery options. Our goal is to provide affordable and convenient access to quality items exactly when our users need them. We are starting with P2P clothing/accessories and expanding to other categories.

We're looking for a technical, product-minded, and dedicated Head of Engineering to lead the development of a platform that's reliable, performant, and built to scale. This is a key leadership role where you'll shape both the technology stack and the engineering culture of the company.

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, , 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