Island Systems, LLC develops and supports Compliance Island™, a CMMC and NIST SP 800‑171 aligned Azure Virtual Desktop enclave deployed into customer‑owned Microsoft Azure environments.
Compliance Island helps organizations reduce CUI risk, accelerate their path toward CMMC Level 2 readiness, and operate a controlled cloud environment without forcing every part of the business into scope.
We are seeking a Senior Azure DevSecOps Engineer who can work across customer support, product improvement, automation, deployment engineering, and technical requirements development.
This is not a narrow help desk role and not just an Azure deployment role. The right person will support customers, improve the product, identify recurring issues, turn those issues into clear feature requirements, and contribute to automation that makes Compliance Island more reliable, repeatable, secure, and scalable.
The Role
As a Senior Azure DevSecOps Engineer for Compliance Island, you will work with our product, support, deployment, and advisory teams to support customer environments and improve the underlying product.
Your work will include:
- Tier 2 and Tier 3 technical support
- Customer environment troubleshooting
- Azure deployment support
- Scripting and automation
- Azure DevOps work item management
- Requirements development
- Documentation
- Product improvement
You should be comfortable in a fast‑moving technical environment where support tickets, customer patterns, product defects, feature ideas, documentation gaps, and automation opportunities all feed into the same product improvement lifecycle.
We are especially interested in candidates who use modern AI tools as part of their normal engineering workflow—troubleshooting, scripting, documentation, requirements analysis, test planning, backlog refinement, and technical research.
The right person does not blindly trust AI output. They validate commands, architecture decisions, security implications, and customer impact.
What You Will DoCompliance Island Product Support
- Provide Tier 2 and Tier 3 technical support for customer environments
- Troubleshoot Azure Virtual Desktop, Azure networking, Entra ID, VMs, security tooling, Microsoft 365, automation, deployment scripts, and customer‑specific configuration
- Review Tier 1 escalations and provide clear guidance
- Improve support runbooks, escalation paths, troubleshooting standards, and knowledge base content
- Identify patterns indicating product defects, missing documentation, poor UX, configuration drift, or automation opportunities
Azure DevSecOps & Automation
- Support and improve automated deployment processes
- Work with Azure Bicep, ARM templates, PowerShell, JSON, Azure DevOps, Git, and GitHub workflows
- Develop and maintain PowerShell scripts for deployment, configuration, validation, support, reporting, and troubleshooting
- Improve infrastructure‑as‑code for repeatability, security, and maintainability
- Test deployment changes, validate parameters, document expected outcomes, and identify failure points
Product Requirements & Feature Development
- Translate support issues and engineering challenges into clear product requirements
- Document requirements for product, engineering, support, and leadership
- Evaluate business value, customer value, support impact, and security/compliance impact
- Distinguish true product requirements from one‑off customer requests
- Contribute to improvements that reduce ticket volume and increase deployment quality
Customer & Team Engagement
- Communicate clearly and professionally with customers and internal teams
- Explain technical issues in plain language
- Maintain a customer‑first mindset while protecting the product and team
- Participate in team meetings, support reviews, product discussions, and deployment planning
- Challenge assumptions and recommend better technical approaches
Documentation & Knowledge Management
- Create and maintain technical documentation, support notes, deployment notes, troubleshooting procedures, and product improvement recommendations
- Use AI tools responsibly to accelerate documentation and improve clarity
- Convert tribal knowledge into repeatable operational procedures
Required Qualifications
- 5+ years of hands‑on Azure engineering, administration, DevOps, cloud infrastructure, or product support
- Strong experience with Microsoft Azure (AVD, VMs, networking, NSGs, Azure Firewall, Storage Accounts, Log Analytics, Defender, Sentinel, Automation Accounts, Entra ID, RBAC, PIM, Azure Gov/GCC High)
- Strong PowerShell scripting experience
- Experience with Azure Bicep, ARM templates, JSON, or IaC
- Experience with Git, GitHub, Azure Repos
- Experience with Azure DevOps Boards, GitHub Issues, Jira
- Ability to troubleshoot Windows client/server and cloud environments
- Ability to read technical documentation and identify gaps
- Strong written and customer‑facing communication skills
- Ability to work independently in a remote environment
- Ability to work as a 1099 contractor or via B2B
Strongly Preferred Qualifications
- Public GitHub profile, portfolio, sample scripts, automation examples, or technical writing
- Experience using AI tools (ChatGPT, Claude, GitHub Copilot, Microsoft Copilot, Cursor, Codex, etc.)
- Experience supporting SaaS, managed services, cybersecurity, compliance, or cloud platforms
- Tier 2/Tier 3 support experience with engineering and automation contributions
- Experience turning customer issues into structured feature requests
- Experience with secure cloud environments, regulated industries, defense contractors, GCC High, Azure Gov, CMMC, NIST SP 800‑171/800‑53, FedRAMP
- Experience with silent software deployment, packaging, endpoint configuration, scripted installs
- Linux administration experience
- Experience creating diagrams, architecture notes, as‑built documentation
- Azure certifications (optional if hands‑on ability is strong)
The Kind of Person Who Will Succeed
- You are a builder, not just an operator
- You are curious, technical, and resourceful
- You use AI daily but validate everything
- You move from ticket → root cause → requirement → better outcome
- You prefer automation over manual repetition
- You work professionally with customers even when the answer is “no” or “not yet”
- You ask good questions and document what you learn
- You understand compliance products must be secure, repeatable, supportable, and well‑documented
This Role Is Not a Fit If
- You only want ticket‑based help desk work
- You are uncomfortable working with customers
- You need fully defined tasks before starting
- You do not enjoy scripting, automation, Git, Azure DevOps, or IaC
- You are not actively using or learning modern AI tools
- You prefer one‑off manual fixes over product improvement
Eligibility Requirements
- Must be a U.S. person (citizen or lawful permanent resident)
- Must be based in the United States
- Must be available during standard U.S. business hours
- Must pass a background check
- Must be able to work as a 1099 contractor or via B2B
Engagement Type & Compensation
This is a 1099 independent contractor or B2B services engagement. Not a W‑2 position.
The engagement is a monthly contract retainer tied to support availability, product support responsibilities, Azure DevSecOps delivery, documentation, automation, and agreed work items. Hourly or milestone‑based structures may be considered.
The ideal contractor is available during standard U.S. business hours and able to support customer‑facing technical operations, Tier 2/Tier 3 escalations, Azure deployment support, product backlog refinement, and automation improvements.
Pay: $125,000.00 - $225,000.00 per year
Work Location: Remote
