AI DevOps Engineer

About Us

SmartAdvocate® is a leading legal case management application. Conceptualized by the founding partner of a prominent personal injury law firm, SmartAdvocate® is offered as either a cloud-based or self-hosted application. Legal professionals use SmartAdvocate to manage pre-litigation and litigation cases including contacts, communications, case data, documents, document scanning and filing, document creation, calendaring, and more.

Our clients run in hybrid environments — on-premises Windows infrastructure and cloud-hosted deployments. The stack is Microsoft-centric: ASP.NET, SQL Server, IIS, and Windows Server, with Oracle Cloud Infrastructure (OCI) as our primary cloud platform.

About The Role

We are looking for a hands-on AI DevOps Engineer to own and build out the operational backbone of our legal case management platform. You will be the go-to person for infrastructure across traditional systems and modern AI workloads, including LLMs, RAG pipelines, vector databases, and agent-based systems.

We are looking for a hands-on Infrastructure & Operations Engineer to own and build out the operational backbone of our legal case management platform. You will be the go-to person for everything infrastructure — from development environments to production deployments across on-premises and cloud-hosted client sites.

This is a high-impact, high-autonomy role. You will be the primary Ops resource, working alongside developers who currently handle infrastructure part-time. Your mission is to bring structure, reliability, and observability to our operations — establishing proper CI/CD pipelines, monitoring, alerting, and incident response processes.

This is an on-site role. No remote applicants. This is not negotiable and will not be revisited.

What You Will Do

Build, Release & AI Deployment

• Design, build, and maintain CI/CD pipelines using Azure DevOps and Jenkins
• Manage build configurations, artifact publishing, and release orchestration
• Coordinate deployments across multiple client environments (on-prem and cloud)
• Maintain and improve source control workflows using Git

Infrastructure Management

• Provision, configure, and maintain Windows Server environments (dev, test, staging, production)
• Administer IIS web servers — application pools, bindings, SSL certificates, performance tuning
• Manage SQL Server instances — installation, configuration, backups, high availability (Always On)
• Maintain networking fundamentals — DNS, firewalls, load balancers, VPN connectivity
• Handle patch management and security hardening across all environments

Monitoring, Observability & AI Systems

• Stand up and maintain monitoring infrastructure using Zabbix, Grafana, and Loki
• Define and implement alerting rules for system health, performance, and availability
• Build dashboards that give the team real-time visibility into all environments
• Establish baseline metrics and SLAs for system performance

Incident Response & Troubleshooting

• Serve as the primary point of contact for production infrastructure issues
• Diagnose and resolve system outages, performance degradation, and deployment failures
• Conduct root cause analysis and implement preventive measures
• Document runbooks and operational procedures for common issues

Security & Compliance

• Implement and maintain access controls, following the principle of least privilege
• Manage SSL/TLS certificates across all environments
• Ensure backup and disaster recovery procedures are in place and regularly tested
• Support security audits and maintain awareness of data protection requirements (legal industry handles sensitive PII)

Required Skills & Experience

• 5+ years of Windows Server administration — this is a Windows shop and you must be an expert
• Expert-level Microsoft SQL Server — installation, configuration, backup/restore, performance tuning, Always On availability groups, index maintenance
• Expert-level IIS administration — application pools, URL rewrite, SSL bindings, troubleshooting, performance optimization
• CI/CD pipeline experience — Azure DevOps Pipelines and/or Jenkins, build automation, release management
• Scripting with PowerShell — automation of routine tasks, deployment scripts, system administration
• Source control — Git workflows, branching strategies, merge management
• Monitoring tools — hands-on experience with at least one observability stack (Zabbix, Grafana, Prometheus, or similar)
• Networking fundamentals — DNS, TCP/IP, firewalls, load balancers, VPN, SSL/TLS
• Backup & disaster recovery — designing and testing backup strategies, point-in-time recovery
• LLM Integration: OpenAI Chat Completions, Assistants API, Realtime API, function calling, streaming. Just knowing the Chat API is not sufficient
• RAG Systems: Vector databases (Chroma or equivalent), embedding models (HuggingFace/OpenAI), chunking strategies, retrieval pipelines
• Agentic Patterns: Tool-calling agents, multi-step reasoning, agent orchestration frameworks (LangChain or equivalent)

Preferred Qualifications

• Microsoft Certification (MCSA, MCSE, or Azure equivalent) — strongly preferred
• Oracle Cloud Infrastructure (OCI) experience — compute, networking, storage, block volumes
• Grafana + Loki experience for log aggregation and visualization
• Zabbix experience for infrastructure monitoring
• Python scripting for automation and tooling
• Docker / containerization basics
• Linux administration fundamentals
• AWS EC2 experience
• Familiarity with compliance frameworks (SOC 2 or similar)
• Experience supporting multi-tenant or client-deployed software products
• What Makes You a Great Fit
• Ownership mentality — you will be building this function, not slotting into an existing team. You see gaps and fill them without being asked.
• Calm under pressure — production issues happen. You diagnose methodically, communicate clearly, and fix things fast.
• Automation-first mindset — if you do something twice, you script it. Manual processes are temporary, automation is the goal.
• Clear communicator — you can explain infrastructure issues to developers and stakeholders in plain language.
• Documentation habit — you write things down so the team doesn't depend solely on your memory.
• Pragmatic problem solver — you find the right solution for the situation, not the theoretically perfect one.

Pay: $100,000.00 - $160,000.00 per year

Benefits:

• 401(k)
• Dental insurance
• Health insurance
• Paid time off
• Vision insurance

Experience:

• Microsoft SQL Server: 3 years (Preferred)
• CI/CD: 4 years (Preferred)
• PowerShell: 3 years (Preferred)
• Disaster recovery: 3 years (Preferred)
• Python: 4 years (Preferred)
• Microsoft Windows Server: 5 years (Preferred)
• AI: 3 years (Preferred)
• LLM: 3 years (Preferred)
• Agentic AI: 1 year (Preferred)

Ability to Commute:

• Melville, NY 11747 (Required)

Work Location: In person