Senior Site Reliability Engineer

At Redwood, we empower our customers with lights-out automation for their mission-critical business processes.

Redwood Software is the leading orchestration platform for the autonomous enterprise, driving business transformation at the lowest total cost of ownership. Redwood empowers organizations to intelligently automate and orchestrate mission-critical business and IT processes across complex ERP, hybrid cloud, data and emerging agentic AI systems. Through its SaaS-first automation fabric—with AI embedded across the automation lifecycle—Redwood accelerates the path to autonomous operations. Backed by 30 years of experience and trusted by more than 50% of the Fortune 50, Redwood helps organizations unlock human potential to focus on innovation, growth and what’s next.

• One Team. One Redwood
• Make Your Own Weather
• Obsess over Customer Success
• Work the Problem
• Be Curious
• Own the Outcome
• Respect Each Other

As a Senior Site Reliability Engineer (SRE) / DevOps Engineer you will be responsible for ensuring the stability, performance, scalability, and reliability of Redwood’s mission-critical SaaS platform. You will apply engineering principles to operational challenges, automate repetitive work, strengthen observability, and collaborate across teams to deliver a resilient and high-performing customer experience.

• Provide day-to-day management of system alerts, monitor system health, and escalate issues as necessary to maintain high availability.
• Participate in a 24x7, team-shared on-call rotation for critical SaaS platform incidents and provide support during emergencies.
• Lead incident response efforts to ensure fast and effective mitigation and resolution of production issues.
• Perform thorough Root Cause Analysis (RCA) and lead blameless post-mortems to identify systemic weaknesses and establish corrective actions that prevent recurrence.
• Collaborate with engineering teams to establish and enforce error budgets derived from Service Level Objectives (SLOs), balancing development velocity with system stability.
• Automate routine operational tasks to reduce manual effort and toil while increasing team efficiency.
• Design, deploy, and maintain cloud infrastructure using Infrastructure as Code (IaC), leveraging Terraform and Helm for deployment to EKS/Kubernetes clusters.
• Design, secure, and troubleshoot AWS cloud network architecture, including VPCs, subnetting, routing, security groups/NACLs, load balancers (ALB/NLB), and VPN/Transit Gateway connectivity across a multi-region, multi-account environment supporting EKS and Docker Swarm on EC2.
• Improve infrastructure health by developing and implementing checks, scripts, and automated remediation to proactively address known issues and enable platform self-healing.
• Maintain, develop, and evolve Continuous Integration/Continuous Delivery (CI/CD) deployment code and pipelines.
• Maintain existing infrastructure running on Docker and Docker Swarm while contributing to migration strategies toward EKS/Kubernetes.
• Implement and integrate new technologies and services into Redwood’s cloud infrastructure to enhance platform capabilities and resilience.
• Design and implement comprehensive observability strategies across metrics, logs, and traces.
• Create and refine robust monitoring and alerting configurations within the EKS/Kubernetes ecosystem.
• Utilize and maintain Datadog to gather performance data, create synthetic tests, configure monitoring, and visualize system health through dashboards.
• Leverage existing monitoring solutions, including Grafana and Prometheus, while supporting the migration or integration of data into a unified observability platform.
• Document issues, remediation steps, system architecture, and runbooks to support knowledge transfer and rapid incident response.
• Collaborate closely with Support, Customer Success, Migration, and Professional Services teams to deliver a high level of SaaS service and minimize customer impact during changes.
• Maintain a strong customer focus when planning deployments and updates, considering the impact on end users before implementing changes.

• 5+ years of experience in Site Reliability Engineering, DevOps, or Cloud Infrastructure roles, ideally supporting a production SaaS platform.
• Hands-on AWS Cloud Engineering experience with strong working knowledge of the AWS ecosystem, including AWS IAM roles and policies.
• Strong knowledge of AWS cloud networking, including VPC design and peering, subnetting, security groups/NACLs, route tables, ALB/NLB load balancers, Transit Gateway/VPN connectivity, and Route 53 DNS.
• Ability to design and troubleshoot connectivity across multi-region, multi-account AWS environments.
• Proficiency with EKS/Kubernetes (K8s) and container orchestration technologies.
• Demonstrated experience with Infrastructure as Code (IaC), specifically Terraform and Helm.
• Working experience with Docker and maintaining systems using Docker Swarm.
• Expertise in implementing and managing logging, monitoring, and observability solutions.
• Direct experience with Datadog, including APM, infrastructure monitoring, synthetic testing, and custom dashboards.
• Experience with Grafana and/or Prometheus is a plus.
• Proficiency working in Linux environments with strong Bash and/or Python scripting skills for automation and troubleshooting.
• Operational experience with relational databases in production environments, such as AWS RDS/PostgreSQL, including performance tuning, backup and restore, and troubleshooting under load.
• Experience providing product or application support for high-availability SaaS products.
• Experience designing, implementing, and operating within a DevSecOps environment.
• Excellent written and verbal communication skills, with the ability to clearly explain complex technical issues and Root Cause Analyses to both technical and customer-facing audiences.

Pay Transparency: The typical base salary range for this position is $125,000 - $145,000 CAD annually. The range represents base salary only, and does not include company bonus, incentive for sales roles, equity or benefits, as applicable. Final compensation will be determined based on the candidate's skills, experience, and relevant qualifications.
Vacancy Status: Existing vacancy
AI Transparency Disclosure: As part of our commitment to hiring transparency and in compliance with Ontario law, please be advised that we utilize artificial intelligence (AI) tools during our interview process. Specifically, we may use an AI-enabled notetaking assistant to help capture and summarize interview discussions. This tool is used solely to assist our hiring team in summarizing candidate information; all final hiring and selection decisions are made exclusively by individuals on the hiring team.