Staff Engineer, Site Reliability

Company shown to members 🔒 · Remote · Canada only

Canada onlySeniorPublished 30 October 2026Check carefully

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First recorded by Psst: 31 October 2026. Your first 3 jobs are free to apply to (the first right away, 2 more with your email). After that, the company and the apply link are for Psst members, from $4.99 for 7 days.

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The 20-second read

Experience
Senior
Where you can live
Canada only
Skills and tools
outreach, aws, kubernetes, terraform, ci/cd, transcription

Read from the ad by Psst's rules. Check the full ad below before applying.

Job details

Where you can work
Canada
Employment type
Not stated by the employer
Advertised pay
Not stated by the employer
Experience
Senior
Employer publication date
30 October 2026
First recorded by Psst
31 October 2026
Last checked at the source
10 November 2026

About the job

How We Build

The company is in the middle of a fundamental shift in how software gets made, and we are not tiptoeing into it. We are rebuilding our engineering culture around a simple belief: AI changes everything. How teams are structured, how decisions get made, how fast ideas become working software. Our engineers own problems end to end, working directly with product, design, and business partners with short feedback loops and real stakeholder access. We ship, learn, and iterate fast. When something is not working, we throw it out and start over — project failure and personal failure are not the same thing here. AI tools are as natural to our workflow as an IDE or version control. We are not exploring this, we are living it. Our engineers use AI to explore tradeoffs, pressure-test designs, and move from problem to solution in hours instead of days. They generate code with AI so they can stay focused on the decisions that actually require human judgment — not the routine ones. More velocity means more time for craft: better test coverage, stronger architecture, and deeper customer understanding. We hold ourselves to a higher quality bar because of AI, not in spite of it. We are building this playbook in real time, and we are looking for people who want to build it with us. If you have already changed how you work because of AI — or you are ready to — and you care more about shipping something great than following a prescribed process, we should talk.

Our Tech Stack

  • Ruby on Rails
  • AWS
  • Sidekiq
  • MySQL
  • Redis

What the Role Is

The company's Platform team is the foundation every engineering team builds on — and this role is at the center of keeping it reliable, fast, scalable, and secure. As a Staff SRE, you'll own the infrastructure and reliability practices that support 9 million+ users and the engineers who build for them. You'll bring strong software engineering skills and experience building security into production systems, turning that experience into code, automation, and secure defaults. You'll evolve our AWS infrastructure, CI systems, and developer tooling as the company grows across e-commerce, registry, health, media, and mobile. You'll share the team's core SRE responsibilities and bring particular depth in security engineering, leading security improvements alongside reliability, developer experience, and platform initiatives.

Who You Are

  • Strong software engineering skills — you've shipped and operated production-quality tools or services, with tests, code review, and maintainable interfaces
  • Experience building security into production systems — you've personally designed, implemented, and operated controls for access, workload identity, secrets, or network isolation
  • Deep hands-on Terraform expertise — you own IaC, not just contribute to it
  • Proven AWS experience at scale — EKS, RDS, cloud networking, DNS, CDNs, load balancers — you know the gotchas
  • Experienced operating Kubernetes in production — you've debugged the hard stuff, not just deployed the easy stuff
  • Comfortable designing and improving CI/CD systems — CircleCI, GitHub Actions, or similar; you care about developer velocity, not just pipeline uptime
  • Strong observability instincts — Datadog, Sentry, PagerDuty, Cronitor — you build alerting that's actionable, not noisy
  • Experienced with on-call and incident management — you've run the post-mortems and actually changed things afterward
  • Comfortable supporting developers across local, staging, and production — you're a resource, not a gatekeeper
  • You naturally reach for AI in your work — at the company, every team uses AI daily. You're already using it to move faster and improve your output, and you stay curious about what's coming next.

How You Will Make An Impact

  • Infrastructure ownership — manage and evolve our AWS environment using Terraform, keeping EKS clusters, databases, and core services current, performant, and secure
  • Software and automation — ship tested tools and services with runbooks and self-service workflows that other engineers can adopt and operate
  • Secure infrastructure defaults — build versioned, tested Terraform modules for least-privilege access, secrets, and workload isolation, with automated checks for configuration drift
  • CI/CD reliability — keep delivery fast and dependable across Engineering, integrating dependency and container scanning, secret detection, and short-lived deployment credentials
  • Developer support — be the person engineers turn to when environments break; unblock them fast across local, staging, and production
  • Monitoring & alerting standards — define service-level objectives (SLOs) and actionable alerting with engineering teams, using incident trends to prioritize reliability improvements
  • Recovery readiness — validate backups, restore procedures, and failover paths through regular recovery tests
  • Incident response — lead or support incident response, drive post-incident reviews, and close the loop so the same thing doesn't happen twice
  • Platform strategy — shape our long-term infrastructure roadmap and lead cross-team initiatives from design through rollout, adoption, and ongoing operation, mentoring engineers along the way

Why This Role

  • Platform is the team every engineering team depends on — your work has outsized leverage across the entire product org, not just one area
  • The infrastructure is solid and actively evolving — you'll shape how reliability and security are built into the platform as it grows
  • This is a staff-level role with real cross-team visibility — you'll influence how the company engineers build and ship, not just keep the lights on
  • You'll work on systems that support millions of families at a high-stakes life moment — the scale is real and the product context makes the reliability work matter

Who We Are

The company is the leading platform for expecting and new families. More than 10 million people shop with the company every year, making it the go-to destination for seamless purchasing, guidance, and expert recommendations. As a modern, AI-forward tech company, the company has expanded from a universal registry into a full ecosystem — the the company Shop, the company Health, the company Money, NYC and LA showrooms, branded content, and more — generating $750M in revenue in 2025. Building the generational brand in baby, the company is reshaping the $235B kids and baby market and helping parents feel confident, connected, and cared for at every step.

Our Ways of Working

The company is remote-first with team members across the U.S. and Canada who move fast, think smart, and use AI as part of how they work every day — not as an experiment, as an expectation. We come together twice a year to build the relationships behind the work, and we hire people who are genuinely excited about what's possible and prove it through how they show up.

Why You Will Love Working At the company

Our Culture

  • We work with focus and intention, then step away to recharge
  • We believe in exceptional management, and we invest in the tools and the time to connect with colleagues
  • We build products that positively impact millions of people's lives
  • AI is part of how we work, not a side experiment. You'll have leading tools like Claude and ChatGPT from day one, with no waiting on access, so the busywork gets handled and your judgment goes where it counts

Growth & Development

  • Competitive pay and meaningful opportunities for career advancement
  • We believe technology and data can solve hard problems
  • We're committed to career progression and performance-based advancement

Benefits

  • Company-paid medical, dental, and vision insurance
  • Retirement savings plan with company matching and flexible spending accounts
  • Generous paid parental leave and PTO
  • Winter Wonder Week: the whole company takes a paid week off at the end of the year, whether or not you celebrate anything, so everyone's out at once and comes back refreshed
  • Remote work stipend to set up your office
  • Perks for physical, mental, and emotional health, parenting, childcare, and financial planning

Important Notices

Recorded Interviews.  The company uses an interview recording tool to record and transcribe interviews for evaluation purposes in accordance with applicable privacy laws. By participating in an interview, you consent to this recording and transcription.

Interview Integrity.  AI is part of how we work at the company. We expect you to use it too. Your application and interviews should still reflect you and your own thinking. We'll tell you when AI is encouraged. Misrepresentation at any stage may result in removal from consideration for this and future roles.

How We Review Applications  We use AI throughout our hiring process to help review, screen, and assess applications. These tools support our team's review; they do not replace it, and every hiring decision is made by a person.

Connections at the company.  If you have a family member or close personal relationship with a current the company employee, please let your recruiter know. This helps us keep our process fair and transparent for everyone.

Protect Yourself from Scams.  All official outreach comes from the the company Talent Team via @the company.com email addresses only. We will never ask for payment or personal financial information. If you receive outreach via WhatsApp, Telegram, or a non-the company email, it's not us. Verify open roles at the company.com/careers.

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