Feeny
Railsware

Senior DevOps Engineer at Railsware (Remote)

Railsware·

Role details

Work type
Remote
Level
Senior

Job description

We are looking for a Senior DevOps Engineer to join our team!

You will own and evolve Mailtrap's production infrastructure — a multi-region AWS platform powering high-volume email sending and testing. You will keep it reliable, secure, and cost-efficient day to day.

You will also lead a key strategic initiative: planning and executing a partial migration of selected workloads from AWS to rented bare-metal / colocation infrastructure to cut costs — a hybrid-by-design effort, not a full cloud exit.

You will decide what moves and what stays, design the target platform (likely Kubernetes or a similar orchestrator on bare metal), and own the migration end to end, from business case to cutover.

Our engineering team thrives in an agile, continuously improving, and automation-oriented environment. We value ongoing evolution, objective evaluation of our processes, and taking action to make things better.

Must have skills

  • 5+ years DevOps/platform (senior), production ownership
  • Deep AWS (VPC, ECS, IAM, RDS/ElastiCache or equivalents, networking)
  • Terraform at scale (modules, remote state / Terraform Cloud)
  • CI/CD with GitHub Actions, including automated deploys to production (e.g. blue/green deployments)
  • Containers (Docker); comfortable operating services on ECS or K8s
  • Strong Linux networking (DNS, TLS, load balancing, firewalls, VPN/hybrid)
  • Proven experience planning and executing migration to on-prem, colo, or private cloud (partial/hybrid OK — full exit not required)
  • Comfortable owning a multi-quarter infra initiative: TCO, design, vendors, cutover, rollback
  • Comfortable automating operational tasks with shell and/or Python
  • Fluent English (both spoken and written)

Strongly preferred

  • Colo/bare-metal ops: IPAM (NetBox), Ansible, image-based provisioning (Packer or equivalent), HAProxy/Nginx
  • Replacing managed AWS services with self-hosted (Postgres HA, Redis/Valkey, Kafka, OpenSearch)
  • Email infrastructure (MTA, SMTP, IP reputation, DKIM/SPF/DMARC) — Halon or similar
  • Cloudflare (DNS/WAF/Access)
  • Observability beyond CloudWatch (Prometheus/Grafana/Loki or equivalent)
  • Prior work with multi-region SaaS or EU data residency
  • Cost-driven architecture / FinOps mindset

Would be a plus

  • GCP (BigQuery/certificates)
  • Comfortable reading Ruby or Go (used in our services and tooling)
  • AWS Certificates

Responsibilities day-to-day

  • Operate and evolve AWS multi-account / multi-region infra
  • Terraform modules/workspaces
  • Ensure safe infrastructure changes across network, storage, and services, with zero-downtime deployments.
  • ECS services, blue/green deploys, Docker image pipelines
  • Reliability: CloudWatch/PagerDuty/Sentry, capacity, cost tags
  • Security baseline: IAM, secrets (SSM), Cloudflare edge rules
  • Partner with engineers on release automation and production readiness
  • Maintain the hybrid estate (AWS and rented bare metal) as one operable platform

Migration leadership

  • Build the business and technical case for what moves off AWS vs what stays
  • Design the rented bare-metal / colo landing zone (compute, network, storage, observability, secrets)
  • Produce migration waves, dependency maps, cutover/rollback plans
  • Stand up hybrid connectivity and dual-run periods; shift traffic safely (e.g. via Cloudflare)
  • Replace or re-home managed services where it pays off (compute, queues, search, cache, MTA nodes)
  • Coordinate colo/vendors, timelines, and eng teams; report progress and risk

Why work at Railsware

  • Remote-first & Flexible: Railswarians live in 25+ countries — fully remote, no fixed schedule, asynchronous communication.
  • Generous Time Off: 34 paid days off per year (24 vacation + 10 national holidays).
  • Smart Expense Policy: An addition sum for workstation, health, learning — “No questions asked” (no bureaucracy).
  • Life-Work Balance: Strong policy against working on weekends, holidays, or outside agreed hours.
  • Strong Team Culture: “I don’t have to carry everything on my shoulders” — experienced, motivated, and accountable peer group. Open feedback, transparency, and holacratic team structure.
  • Growth Support: Individual development plans, conferences, and a culture that encourages learning any skill relevant to your role.
  • Secure Equipment: You choose your workstation.
  • Hiring Practices: Values ownership, empathy, transparency, and quality. Typical hires are senior-level (Full-Stack, QA, Account Managers, etc.).
  • Engineering Culture: Spec-driven development; early-stage involvement in product decisions; technology stack includes Rails, React, mobile, and modern cloud infra.

Application questions