Senior Cloud Automation & Platform Engineer

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 eliminate manual intervention across our infrastructure, deployments, and data movement. You will own the “machine that builds the machine” — the systems that provision infrastructure, ship code, migrate data, and validate correctness automatically.

This role is especially critical as we migrate from AWS Lambda + DynamoDB to a modern containerized and edge-based stack backed by Postgres. You will build the software that moves our data, verifies its integrity, and makes the migration repeatable, observable, and boring.

If you enjoy building automation that replaces tribal knowledge, turning risky one-off operations into deterministic pipelines, and owning platform reliability end-to-end, this role is for you.

Key Responsibilities

1. Infrastructure as Code & Cloud Platform Ownership

• Manage our AWS and Vercel infrastructure entirely through code.

• Own Infrastructure as Code using Terraform, Pulumi, or AWS CDK.

• Eliminate “ClickOps” by ensuring all environments are reproducible and auditable.

• Own AWS configuration and security, including:

• IAM roles and policies

• S3 bucket policies

• OpenSearch clusters

• VPC networking and security groups

• Implement automated cost controls and visibility into cloud spend.

• Build deep observability pipelines using tools like Datadog and Sentry.

• Ensure alerts surface issues before customers notice them.

2. Data Migration Automation (DynamoDB → Postgres)

• Treat migration as software, not a script.

• Design and build a robust ETL pipeline that:

• Extracts data from DynamoDB

• Transforms NoSQL documents into relational schemas

• Loads data into Postgres (Supabase)

• Handle schema evolution, partial failures, retries, and resumability.

• Build automated validation tools that prove data integrity.

• Be able to answer “Did we lose any data?” with a definitive, auditable “No.”

• Automate dry runs so the migration can be rehearsed dozens of times before final cutover.

• Ensure the production migration is predictable, observable, and low stress.

3. CI/CD & Testing Automation

• Design and maintain advanced GitHub Actions workflows.

• Optimize CI performance using intelligent caching and dependency-aware builds.

• Ensure only affected packages and services deploy in our Turborepo.

• Build automation that provisions ephemeral infrastructure for testing.

• Enable preview environments for pull requests, including:

• Temporary deployments

• Seeded databases

• End-to-end test execution

• Treat CI/CD as a product that developers trust and enjoy using.

Required Qualifications

• 4+ years of experience in Cloud, Platform, or DevOps engineering roles.

• Strong experience operating production systems in AWS.

• Automation-first mindset with strong scripting skills (Python, TypeScript, or Bash).

• Proven experience migrating data between disparate systems (e.g., NoSQL to SQL).

• Deep understanding of data transformation, validation, and failure handling.

• Expert-level experience with Infrastructure as Code (Terraform, Pulumi, or AWS CDK).

• Strong understanding of Docker and container lifecycles.

• Experience building and maintaining CI/CD pipelines in GitHub Actions.

Nice to Have

• Experience with self-hosted GitHub Actions runners.

• Experience supporting compliance or security audits.

• Familiarity with Postgres performance tuning.

• Experience operating systems across AWS and Vercel simultaneously.

• Prior ownership of large-scale data migrations or platform rewrites.

First 10 Weeks: What You’ll Ship

• Migration rig: Build an automated pipeline that migrates data from DynamoDB to Postgres, complete with integrity verification and reporting.

• Monorepo CI/CD: Re-architect GitHub Actions to support our Turborepo, enabling concurrent and dependency-aware builds across Web, Mobile, and Backend.

• Observability dashboard: Centralize logs and metrics from AWS, Vercel, and Postgres into a single “pane of glass” dashboard in Datadog, or similar.

Our Desired Stack

• Cloud: AWS (S3, OpenSearch, Cognito, IAM, VPC), Vercel

• Infrastructure as Code: Terraform, Pulumi, or AWS CDK

• CI/CD: GitHub Actions

• Scripting: Python, TypeScript, Bash

• Database: DynamoDB and RDS (source), Postgres / Supabase (destination)

• Architecture: Turborepo, Containerized Services

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