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Caseware

Posted 1 month ago

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Staff Site Reliability Engineer

TorontoRemote

AI Summary

Staff Site Reliability Engineer designing, building, and operating reliable, secure, scalable cloud-native systems on AWS and Kubernetes. They will define SLOs, improve observability, automate CI/CD and incident management, and mentor engineering teams.

About this role

Caseware is one of Canada's original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles!

This is a hands-on senior engineering role focused on improving production resilience, strengthening security, driving operational excellence, and enhancing the developer experience across the organization.

In this role, you will design, build, and evolve the foundational systems, tooling, and operational practices that enable engineering teams to ship secure, reliable, and scalable software with confidence. You will help establish reliability standards, define service level objectives (SLOs), improve observability, automate operational processes, and drive incident management and post-incident learning practices that strengthen platform stability over time.

Partnering closely with Engineering, Security, Platform, and Product teams, you will architect scalable distributed systems, optimize Kubernetes and AWS-based infrastructure, and build automated delivery pipelines that support rapid and safe software releases. You will play a key role in reducing operational toil, improving system performance, increasing platform reliability, and ensuring that our infrastructure can support continued business growth.

❗ This is a full-time permanent position

❗ This is an existing vacancy

📍 Location: This is a remote location open to candidates legally authorized to work in Canada.

What you will be doing:

  • Drive reliability engineering initiatives and operational excellence for mission-critical services running on AWS and Kubernetes.
  • Design, implement, and continuously improve deployment, release, and rollback strategies across complex distributed systems.
  • Establish secure-by-default CI/CD pipelines with robust automation, governance, and policy-driven controls.
  • Enhance platform observability through metrics, logs, tracing, and actionable alerting to improve system visibility and operational efficiency.
  • Define, implement, and mature Service Level Indicators (SLIs), Service Level Objectives (SLOs), and reliability standards across the organization.
  • Lead response efforts for high-severity incidents, ensuring timely resolution, effective communication, and meaningful post-incident reviews that drive continuous improvement.
  • Partner closely with engineering teams to strengthen platform standards, improve service resilience, optimize runtime performance, and embed reliability best practices.
  • Mentor and guide engineers on cloud-native technologies, site reliability engineering principles, and operational excellence practices, fostering a culture of continuous learning and accountability.

    • What you will bring:

  • 8+ years of experience in Site Reliability Engineering (SRE), Platform Engineering, DevOps, or related cloud-native engineering roles.
  • Deep expertise in AWS services, including EKS, IAM, VPC, Lambda, CloudFront, S3, and cloud networking/security best practices.
  • Advanced experience operating and scaling production Kubernetes environments.
  • Strong hands-on experience with Istio service mesh, including traffic management, security, observability, and resiliency.
  • Proven expertise with Infrastructure as Code (IaC), preferably using AWS CDK.
  • Experience building and managing CI/CD pipelines using GitHub Actions or similar platforms.
  • Strong troubleshooting, performance optimization, and incident management experience in distributed systems.
  • Excellent communication, collaboration, and technical leadership skills.

    • Observability & Reliability

  • Experience designing and operating monitoring, logging, tracing, and alerting solutions for cloud-native platforms.
  • Strong knowledge of AWS CloudWatch, OpenTelemetry, AWS X-Ray, and Kubernetes observability tooling.
  • Experience defining and operationalizing SLIs, SLOs, alerting strategies, runbooks, and reliability metrics.
  • Proven ability to leverage observability data to improve service reliability, reduce incident impact, and optimize operational performance.

    • Software Engineering & Platform Development

  • Strong proficiency in TypeScript and Node.js for platform engineering, automation, and operational tooling.
  • Experience building and maintaining scalable backend services, APIs, and event-driven systems.
  • Deep understanding of Kubernetes architecture, controllers, Gateway API, ingress management, and service networking.
  • Experience implementing zero-trust architectures, mTLS, and service-to-service security controls.
  • Commitment to high-quality engineering practices, including automated testing, code reviews, and observability-driven development.
  • Strong understanding of resilience engineering, including autoscaling, disruption management, failure testing, and safe deployment strategies.

    • Nice to Have

  • Experience with progressive delivery practices such as canary, blue/green, and feature-flag-based deployments.
  • Experience working in regulated, compliance-driven, or security-sensitive SaaS environments.
  • Familiarity with FinOps principles and cost optimization strategies for cloud platforms.
  • Experience building internal developer platforms and self-service engineering tooling.
  • Cloud-native certifications such as CKA, CKAD, CKS, KCSA, or KCNA.
  • Kubestronaut certification or equivalent advanced Kubernetes expertise is highly regarded.

    • Skills

    AWSAWS CDKAWS X-RayCI/CDCloudWatchEKSFinOpsGitHub ActionsIaCIstioKubernetesKubestronautNode.jsObservabilityOpenTelemetrySLISLOTerraformTypeScript

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