Senior DevOps Engineer

Senior DevOps Engineer Fully Remote • Toronto, ON - Toronto, Ontario M5E 1E5 1W7 Quick Apply Overview Salary Range $140,000.00 - $170,000.00 Salary Quick Apply Description CARET brings the latest in technology and automation to over 10,000 legal and accounting firms, empowering highly skilled professionals to refocus their expertise on what truly matters. CARET harnesses powerful and secure practice management, document automation, and payment processing to take firms, professionals, and their clients further. Our team-defined values guide how we show up for each other, for our partners, and for our customers: We succeed together. We embrace progress. We care big. We create space. ROLE OVERVIEW The Senior DevOps Engineer designs, automates, and operates secure, scalable, and resilient Microsoft Azure cloud platforms. This role serves as a senior technical owner across infrastructure, CI/CD, Kubernetes, networking, security, observability, and data services. The position leads complex platform initiatives, establishes engineering standards, drives architectural decisions, and partners with development teams to improve platform reliability, operational excellence, and developer productivity. What Success Looks Like Own complex Azure platform initiatives from architecture and design through implementation, production readiness, and ongoing optimization. Anticipate operational, security, scalability, and reliability risks, then implement durable solutions before they affect customers or the business. Raise engineering maturity through reusable automation, clear standards, documentation, mentoring, and measurable continuous improvement. Balance speed, reliability, security, cost, and maintainability when making technical decisions. Key Responsibilities Technical Leadership & Platform Strategy Act as a senior technical authority for Azure platform architecture, cloud-native DevOps practices, and production operations. Lead the design and delivery of scalable SaaS infrastructure, including technical planning, architecture reviews, implementation, validation, and operational handoff. Define and promote platform standards, reference architectures, guardrails, and engineering best practices. Mentor engineers, provide thoughtful technical guidance, and lead cross-functional troubleshooting and design discussions. Evaluate platform capabilities and recommend improvements that strengthen reliability, security, developer experience, and cost efficiency. Infrastructure & Networking Design, deploy, automate, and manage enterprise Azure infrastructure using repeatable, supportable patterns. Own solutions involving Virtual Machines, VM Scale Sets, Managed Disks, DNS Private Resolvers, Private and Public DNS Zones, Application Gateway, Load Balancers, Virtual Network Gateway, Private Endpoints, Virtual Networks, and NAT Gateway. Lead capacity planning, network design, resiliency planning, lifecycle management, and infrastructure optimization. Containerization & Application Platforms Architect, build, and operate modern cloud-native application platforms using Azure Kubernetes Service (AKS), Azure Container Registry (ACR), App Services, and Function Apps. Establish secure and reliable patterns for container deployment, workload scaling, configuration, upgrades, and production support. Partner with application teams to improve deployment consistency, performance, and platform usability. CI/CD, Testing & Release Automation Design and maintain Infrastructure as Code and configuration automation using Terraform and Ansible. Own Azure DevOps pipelines and automated build, deploy, validate, rollback, and release processes. Develop reusable modules, templates, and golden images using Packer and Azure Compute Gallery. Improve release quality through automated validation, policy enforcement, controlled change, and clear deployment standards. Database & Data Services Design, deploy, automate, and support Azure SQL Database, SQL Elastic Pools, PostgreSQL Flexible Server, and Elastic Job Agent. Partner with engineering teams on availability, security, performance, scaling, backup, recovery, and operational readiness for managed data services. Security, Identity & Governance Embed security into infrastructure and delivery practices through secure-by-default architecture and automation. Implement and govern Azure External Directories, Managed Identities, Key Vault, Security Groups, secrets management, RBAC, and least-privilege access. Identify control gaps, lead remediation, and help ensure cloud services align with organizational security and compliance requirements. Monitoring, Observability & Reliability Engineering Build proactive monitoring, alerting, logging, tracing, and performance management solutions using Datadog and OpenTelemetry connectors. Define service health indicators, improve operational visibility, and use reliability data to prioritize platform improvements. Participate in on-call and incident response; lead complex incident triage, root cause analysis, corrective actions, and prevention efforts. Drive reliability practices that reduce repeat issues and improve recovery time. Integration, Automation & AI Services Enable secure application integration and event-driven architectures using API Management (APIM), Logic Apps, Service Bus, and App Configuration. Support the deployment, governance, monitoring, and operation of Azure OpenAI, Azure AI Foundry, AI Foundry Projects, and Document Intelligence. Create automation that reduces manual effort, improves consistency, and enables teams to deliver safely at scale. Qualifications Advanced knowledge of systems, cloud architecture, networking, identity, security, and production operations. Demonstrated experience designing, building, deploying, and maintaining scalable SaaS solutions in Microsoft Azure. Deep hands-on experience with Infrastructure as Code, CI/CD, containers, Kubernetes, observability, and automation in enterprise environments. Experience leading complex technical initiatives with multiple stakeholders, dependencies, and production risks. Strong incident management and troubleshooting skills across application, platform, network, security, and data layers. Ability to translate business and engineering needs into pragmatic, secure, and maintainable technical solutions. Clear written and verbal communication, including the ability to explain technical tradeoffs to technical and non-technical partners. Senior-Level Capabilities Takes end-to-end ownership and operates effectively with limited direction. Uses sound judgment when requirements are ambiguous and escalates material risks with clear options and recommendations. Influences technical direction through expertise, credibility, collaboration, and measurable outcomes. Proactively identifies systemic issues and resolves root causes rather than relying on short-term fixes. Builds strong partnerships across Engineering, Security, Product, and other business functions. Is detail-oriented, security-minded, customer-aware, and committed to continuous improvement. Benefits: Flexible PTO Medical, Dental, Paid Sick Days, Vision, and Supplemental Coverage Flexible Spending Account Health Savings Account 401(k) match If you are not sure that every qualification on the list above describes you exactly, we'd still love to hear from you! We value people with unique backgrounds, experiences, and skillsets. If you’re passionate about having a significant impact and shaping the foundations of a rapidly growing product, please apply! Equal Employment Opportunity: CARET is an Equal Opportunity, Affirmative Action Employer. The compensation information below is provided in compliance with job posting disclosure requirements. Pay range: $140,000 - $170,000 CAD Actual base pay will depend on varying circumstances, including the position, location, individual qualifications, market finances, and other operations business needs.