Head of Engineering

Pickle; New York (NY); On-site; USD 135,000 - 350,000; Full time

Job summary

An innovative rental marketplace is seeking a dynamic Head of Engineering to lead the development of a scalable platform. In this key leadership role, you will shape the technology stack and engineering culture, overseeing mobile, web, and backend platforms. Collaborating closely with cross-functional teams, you'll drive features that enhance user experience and marketplace health. If you're passionate about building robust systems and mentoring engineers, this is your chance to make a significant impact in a fast-paced environment. Join a forward-thinking company that values creativity and collaboration!

Benefits

Competitive compensation and equity

Healthcare (Medical, Dental, Vision)

Flexible paid time off

Meal Pal credits

Desk setup stipend

Professional coaching and training

Team events and company parties

Company offsites

Office space in NYC

Pickle credits for employees

Qualifications

• 6+ years in software engineering, with 2+ years managing teams.
• Experience building and scaling consumer-facing platforms.
• Strong engineering skills with a focus on UX and clean code.

Responsibilities

• Oversee development of mobile, web, and backend platforms.
• Manage and grow a high-performing engineering team.
• Collaborate with Product and Design to enhance user experience.

Skills

Software Engineering

Team Management

React Native

Next.js

AWS Developer Services

Full-stack Architecture

CI/CD Practices

User Experience (UX)

Strategic Mindset

Education

Bachelor's Degree in Computer Science

Master's Degree in Engineering

Tools

Git

Jira

Slack

Job description

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Must Be Located In NYC (we Are In Office Monday - Thursday). Please Apply By Emailing [e-mail] 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

• 6+ years of experience in software engineering, with at least 2+ 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

Seniority level

• Seniority level

  Director

Employment type

• Employment type

  Full-time

Job function

• Job function

  Engineering and Information Technology

• Industries

  Software Development

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