Staff Engineer, Site Reliability

Description

The company is rebuilding how software gets made around the belief that AI changes how teams are structured, how decisions are made, and how quickly ideas become working software.

Engineers own problems from start to finish and work directly with product, design, and business partners, with short feedback loops and direct access to stakeholders. Work that is not succeeding gets dropped and restarted, and a failed project is not treated as a personal failure.

Engineers use AI to test tradeoffs, review designs, and get from a problem to a solution in hours rather than days, and they hand routine code to AI so their time goes to decisions that need human judgment. The extra speed goes into test coverage, architecture, and understanding customers, with a higher quality bar.

The company is still defining this way of working and wants people who have already changed how they work because of AI, or are ready to, and who care more about shipping something strong than following a fixed process.

The stack is Ruby on Rails, AWS, Sidekiq, MySQL, and Redis.

The Platform team supports every engineering team. This Staff SRE role keeps that platform reliable, fast, scalable, and secure for over 9 million users and the engineers who build for them. You bring deep security engineering on top of the team's shared SRE work and lead security improvements alongside reliability, developer experience, and platform projects.

The company serves expecting and new families. More than 10 million people shop with it each year, it generated $750M in revenue in 2025, and it runs a shop, health and money offerings, and showrooms in NYC and LA.

Responsibilities

• Manage and evolve the AWS environment with Terraform, keeping EKS clusters, databases, and core services current, fast, and secure.
• Build and ship tested tools and services, with runbooks and self-service workflows that other engineers can adopt and run.
• Create versioned, tested Terraform modules that enforce least-privilege access, secrets handling, and workload isolation, with automated checks for configuration drift.
• Keep delivery fast and dependable across Engineering by adding dependency and container scanning, secret detection, and short-lived deployment credentials to CI/CD.
• Be the person engineers go to when environments break, and get them unblocked quickly in local, staging, and production.
• Define SLOs and actionable alerting with engineering teams, and use incident trends to decide which reliability work comes first.
• Validate backups, restore procedures, and failover paths through regular recovery tests.
• Lead or support incident response, run post-incident reviews, and make sure the same failure does not happen again.
• Shape the long-term infrastructure roadmap and lead cross-team initiatives from design through rollout, adoption, and ongoing operation, mentoring engineers along the way.

Requirements

• Strong software engineering skills, with experience shipping and operating production-quality tools or services that include tests, code review, and maintainable interfaces.
• Experience designing, building, and running access, workload identity, secrets, or network isolation controls in production systems.
• Deep hands-on Terraform experience, including owning infrastructure as code rather than only contributing to it.
• Proven experience running AWS at scale, including EKS, RDS, cloud networking, DNS, CDNs, and load balancers, and knowing their pitfalls.
• Experience operating Kubernetes in production and debugging hard problems, not only deploying workloads.
• Experience designing and improving CI/CD systems such as CircleCI, GitHub Actions, or similar, with a focus on developer velocity.
• Strong observability judgment with tools such as Datadog, Sentry, PagerDuty, or Cronitor, and a habit of building alerts that are actionable rather than noisy.
• Experience with on-call work and incident management, including running post-mortems and making real changes afterward.
• Comfortable helping developers across local, staging, and production as a resource rather than a gatekeeper.
• You already use AI daily to move faster and improve your work, and you keep up with what comes next. Every team at the company uses AI every day.

Conditions

The role is remote, and the team is spread across the U.S. and Canada; the company gets everyone together in person twice a year.

AI tools such as Claude and ChatGPT are available from day one, with no waiting for access.

The starting salary range is $226,673 to $271,991. Starting pay depends on location, experience, and qualifications, and raises are tied to performance, growth in the role, and internal pay equity.

Interviews are recorded and transcribed for evaluation under applicable privacy laws, AI helps review applications but people make every hiring decision, misrepresentation at any stage may lead to removal from this and future roles, and you should tell your recruiter about any close relationship with a current employee.

Benefits

• Company-paid medical, dental, and vision insurance.
• A retirement savings plan with company matching, plus flexible spending accounts.
• Generous paid parental leave and PTO.
• A paid week off for the whole company at the end of the year, so everyone is out together and returns rested.
• A remote work stipend to set up your home office.
• Perks covering physical, mental, and emotional health, parenting, childcare, and financial planning.
• A target annual bonus of 20% and competitive equity.