Senior Platform Engineer

Senior Platform Engineer

At Squaremouth, our mission is simple: make travel insurance easy. We take complicated insurance products and turn them into a clear, simple comparison experience so travelers can find the coverage that gives them peace of mind. Our engineers play a huge role in making that possible.

We're looking for a Senior Platform Engineer to join our small, fast-moving team and help us level up platform engineering across reliability, automation, and developer experience. You'll lead our push toward Infrastructure as Code, strengthen our security and observability foundations, and build the tooling and guardrails that make it easy for engineers to adopt AI and agent-driven workflows as we scale.

This is a fully remote role. We're based on US Eastern Time, and we welcome candidates who can collaborate during those hours.

What You'll Do

• Own production reliability on AWS (availability, performance, capacity planning).
• Lead our move to Infrastructure as Code (likely Terraform): versioned, reviewed, repeatable infra changes.
• Improve CI/CD and release workflows for our Ruby and Wordpress apps (safer rollouts, faster deploys, easy rollbacks).
• Run and evolve our container platform (Docker + Swarm today), and help plan a pragmatic modernization path.
• Build and maintain internal developer tooling (Ruby) for provisioning, deployments, and operational workflows.
• Strengthen security by default (least-privilege IAM, secrets, network isolation, patching cadence).
• Upgrade observability (logs/metrics/traces), alerts, and dashboards so debugging is fast and predictable.
• Enable AI/agent workflows with the right infrastructure + guardrails (credentials, sandboxes, evals, cost controls).

What We're Looking For

• Strong hands-on AWS production experience (IAM, networking, compute, databases, monitoring).
• Proven experience implementing IaC at scale (patterns, modules, environments, workflow).
• Solid Linux + networking fundamentals; calm, effective incident debugging.
• Strong DevEx mindset: automation, tooling, CI/CD, and pragmatic platform improvements.
• High ownership in a small team: set direction, ship, document, and bring others along.

Bonus Points For Experience With

• Container platform migration experience (Swarm → ECS/EKS/Kubernetes, or similar).
• Ruby (or strong scripting) for internal platform and automation tooling.
• Experience operationalizing AI/agents (security, cost controls, evals, observability).
• Hands-on configuration management (Ansible/Chef/Puppet) and comfort managing config drift across environments.

Why You'll Love Working Here

• Salary: $100,000–$150,000 + bonus, depending on experience
• 401(k) match
• You'll have a voice: we involve engineers in major decisions
• Remote-first: work from wherever you do your best work
• Small team, big impact: your work directly shapes a product used by millions of travelers
• Generous PTO: flexibility to take the time you need to rest and recharge

We're a tight-knit team that's been simplifying travel insurance since 2003. We built Squaremouth to be a great place to work and the easiest way for travelers to find coverage that fits. In 2014, we launched Tin Leg, our own travel insurance brand focused on real traveler needs. It quickly became one of the most popular options on squaremouth.com.

Today, we're more than 50 people who still move fast and care deeply about customers and teammates. We've been recognized as one of the Best Workplaces in America by Inc. Magazine and take pride in building both a great product and a great culture.

In 2023, we joined Specialty Program Group (SPG), giving us the resources to grow while keeping our startup spirit. So far, we've helped over 4 million travelers find coverage that gives them peace of mind, and we're just getting started.