Senior IT Systems Engineer

Cloud Employee is a UK-owned business established eight years ago. We connect high-performing software engineers with some of the world’s most innovative tech companies. Our developers work as part of international engineering teams, gaining global experience while growing their technical and professional skills.

We pride ourselves on being a supportive workplace that invests in learning, engagement, and long-term career development. We offer stability, career progression, and tailored training and mentoring to help every engineer reach their potential.

Our client is a fast-growing Managed Service Provider (MSP) supporting clients across healthcare, finance, retail, and other sectors. They’re modernizing their operations by building an internal automation function that reduces manual work, minimizes risk, and drives efficiency.

The company operates across the US, Portugal, and the Philippines, with a culture that values clear communication, critical thinking, and the confidence to challenge risky or inefficient ideas.

We’re hiring a Senior IT Systems Engineer (Automation) to own and evolve the internal automation stack. You’ll work closely with engineering and support teams to translate pain points into intelligent automation solutions, ensuring reliability and security at every step.

• Design, develop, and maintain internal automation scripts, integrations, and workflows.
• Build and improve automation for Level 1 and 2 support processes (user provisioning, deployments, troubleshooting).
• Manage and optimize RMM and ITSM tool configurations (e.g., Datto, ConnectWise, Kaseya, Autotask).
• Collaborate with distributed teams to gather requirements, evaluate risks, and implement scalable solutions.
• Document systems, processes, and automation logic clearly and consistently.
• Act as an internal consultant, providing guidance on automation feasibility, impact, and best practices.

• 5+ years in IT systems engineering or automation roles.
• Advanced PowerShell scripting for Windows environments.
• Working knowledge of Python for automation tasks.
• Hands-on experience with Datto RMM or similar tools (ConnectWise, Kaseya, Autotask).
• Familiarity with Microsoft 365, Active Directory, and endpoint management.
• Experience with AI/ML automation tools (e.g., PIA AI, OpenAI, Azure AI).
• Solid understanding of Level 1 and 2 support workflows.
• Excellent English communication skills, written and spoken.

• Experience with DevOps tools (Git, Jenkins, Terraform).
• Familiarity with Rocket Cyber or other security automation platforms.
• Cloud platform experience, especially Azure.
• Background in data analytics or reporting.
• Experience deploying internal security tooling.

The ideal candidate is a self-driven problem solver who knows when to challenge an idea and when to build it better. They think critically, communicate clearly, and enjoy working independently while collaborating across teams.

• Think critically and question unsafe or inefficient automation requests.
• Communicate clearly and diplomatically push back when needed.
• Translate vague requests into clear, scalable solutions.
• Are detail-oriented, organized, and disciplined with documentation.
• Enjoy improving systems without overcomplicating them.
• Can work autonomously and take full ownership of your stack.
• Have experience working remotely with global teams.

• Competitive compensation package in USD
• 15 PTO days per year.
• Health insurance allowance.
• USD 1,000 annual learning and development budget.