Octopus Deploy Engineer (Contractor – Remote)

This is a remote position.

Octopus Deploy Engineer (Contractor – Remote)

Clear Measure is seeking a skilled Octopus Deploy Engineer (Contractor) to join our remote team. In this role, you will take ownership of inspecting, designing, implementing, and supporting Octopus Deploy environments for our clients. Your focus will be on automating and streamlining deployment pipelines to ensure reliable and consistent application delivery across multiple environments.

Responsibilities:

• Architect, implement and maintain Octopus Deploy infrastructure to support scalable, multi-environment application deployments.
• Configure and manage Octopus Deploy projects, releases, and processes to support CI/CD workflows.
• Collaborate closely with internal teams and clients to ensure successful, best-practice-driven software deployments.
• Continuously improve automation scripts and deployment processes for enhanced reliability and efficiency.
• Troubleshoot Octopus Deploy-related issues and support resolution across infrastructure, script, or process layers.
• Develop documentation for infrastructure, deployment processes, client training, and troubleshooting guides.
• Maintain an internal Octopus Deploy demo environment for testing and presentations.
• Stay current with Octopus Deploy features, updates, and industry best practices.
• Manage client requests through a ticketing system and escalate to the appropriate support tier when needed.
• Provide regular project updates and maintain proactive communication with clients and team members.
• Confidently interact with clients, providing support and training as needed.
• Complete relevant Octopus Deploy certifications and training.

Requirements

• 3+ years of hands-on experience designing, implementing, and maintaining Octopus Deploy infrastructure in production environments.
• Firm grasp of modern software deployment practices, including CI/CD pipelines and release management.
• Proficient with Microsoft platform development tools, including C#, PowerShell, and .NET, in both Windows and Linux hosting environments.
• Experience deploying applications to on-premises and cloud platforms such as Azure and AWS using Octopus Deploy, Azure DevOps, or similar automation tools.
• Solid understanding of networking concepts, including firewalls, VPNs, and load balancers.
• Demonstrated experience working within ticketing systems to manage tasks, respond to client requests, and track progress.
• Familiarity with change management protocols and compliance frameworks such as HIPAA, PCI, PCI DSS, and ISO 27001.
• Skilled in writing advanced PowerShell scripts and using Azure CLI, ARM templates, and Bicep for automation and infrastructure provisioning.
• Comfortable with PowerShell, Bash, or Python scripting for deployment and monitoring tasks.
• Experience with centralized logging and monitoring tools such as Application Insights, Seq, DataDog, SumoLogic, Site24x7, and ElasticStack, including creating custom client dashboards.
• Strong experience managing Windows and Linux server environments.
• Familiar with DevOps tools like Azure DevOps, GitHub Actions, and others (bonus if experienced).
• Working knowledge of Agile methodologies and collaborative development environments.
• Excellent problem-solving, troubleshooting, and communication skills.
• A client-focused, servant-leader mindset, with a passion for delivering high-quality results.
• A self-motivated and lifelong learner who actively stays current with new tools, trends, and best practices in the DevOps and deployment space.

Preferred Qualifications:

• Hands-on experience with Octopus Deploy Runbooks, step templates, and custom deployment scripting.
• Background in a professional services environment, particularly where time is tracked and billed to clients.
• Familiarity with Docker containers and container-based deployment practices.
• Bachelor’s degree in Computer Science, related technical field, or equivalent professional experience.