Welcome to workpinnacle – Where Innovation Meets Flexibility
At workpinnacle, we are redefining the future of technology infrastructure by blending cutting‑edge automation with robust Windows system engineering. Our mission is to empower businesses worldwide with seamless, secure, and scalable cloud solutions that drive operational excellence. As a leader in the digital transformation space, workpinnacle invests heavily in open‑source technologies, continuous learning, and a culture that celebrates diversity, collaboration, and forward‑thinking problem solving. If you thrive in a fast‑paced, remote environment where your expertise directly shapes the next generation of infrastructure automation, you’ve found your next career home.
Position Overview – Remote Windows Systems Engineer (Automation Focus)
We are seeking an experienced, self‑motivated Windows Systems Engineer to join our high‑performing Web Systems Engineering team. This role is 100 % remote, offers an immediate start, and is designed for professionals who excel at both Windows server administration and the development of automation pipelines using Jenkins, Ansible, Terraform, and PowerShell. You will be instrumental in migrating legacy provisioning tools to modern, open‑source frameworks, ensuring that workpinnacle’s cloud‑native environments are reliable, repeatable, and secure.
Key Responsibilities
- Windows Server Administration: Design, deploy, and maintain Windows Server environments (2016/2019/2022) across public cloud platforms such as Azure and Google Cloud Platform (GCP).
- Automation Development: Build, test, and refine Ansible playbooks and Terraform modules that automate the provisioning, configuration, and patching of Windows workloads.
- Jenkins Pipeline Integration: Create and maintain Jenkins pipelines that trigger automated builds, tests, and deployments for Windows‑based services.
- PowerShell Scripting: Write clean, modular PowerShell scripts to streamline routine administrative tasks, enforce compliance, and support self‑service capabilities.
- Version Control & Collaboration: Use GitHub (or equivalent) for source control, code reviews, and collaborative development with cross‑functional teams.
- Monitoring & Incident Response: Implement robust monitoring solutions, respond to alerts, and conduct root‑cause analysis for Windows infrastructure incidents.
- Documentation & Knowledge Sharing: Produce clear, concise documentation for automation workflows, system architecture, and operational procedures.
- Mentorship & Team Collaboration: Partner with junior engineers, share best practices, and contribute to a culture of continuous improvement within the 29‑engineer Web Systems Engineering team.
- Tool Migration & Open‑Source Advocacy: Lead the transition from proprietary tools (e.g., vRealize Automation) to open‑source alternatives, championing community‑driven solutions.
- Security & Compliance: Ensure all automation scripts and infrastructure components adhere to industry security standards and internal compliance policies.
Essential Qualifications (Must‑Haves)
- 5+ years of hands‑on experience in Windows Server system engineering, including design, deployment, and lifecycle management.
- Proficiency with PowerShell scripting and a solid understanding of GitHub for version control and collaborative development.
- 4+ years of experience writing automation scripts using open‑source tools such as Ansible and Terraform; experience with Azure Resource Manager (ARM) templates or GCP Deployment Manager is a plus.
- Demonstrated success supporting Jenkins pipelines and Ansible playbooks specifically for Windows OS provisioning.
- Strong portfolio of publicly available or private GitHub repositories showcasing automation scripts, playbooks, or infrastructure‑as‑code projects.
- Excellent problem‑solving abilities, with a track record of diagnosing complex Windows infrastructure issues and delivering effective solutions.
- Ability to start within two weeks of receiving an offer and commit to a contract through the end of the calendar year, with potential for conversion to a permanent role.
Preferred Qualifications (Nice‑to‑Have)
- Certifications such as Microsoft Certified: Azure Administrator Associate, Red Hat Certified Engineer (RHCE), or HashiCorp Certified: Terraform Associate.
- Experience with containerization technologies (Docker, Kubernetes) on Windows nodes.
- Familiarity with security frameworks (CIS Benchmarks, NIST) and compliance automation.
- Background in DevOps culture, including continuous integration/continuous deployment (CI/CD) best practices.
- Previous work in a fully remote, distributed team environment.
Core Skills & Competencies
- Technical Acumen: Deep knowledge of Windows OS internals, networking, Active Directory, and cloud networking concepts.
- Automation Mindset: Passion for turning manual processes into repeatable, code‑driven workflows.
- Collaboration: Strong communication skills, able to articulate technical concepts to both technical and non‑technical stakeholders.
- Adaptability: Comfortable navigating fast‑changing technology stacks and evolving business priorities.
- Attention to Detail: Meticulous approach to scripting, documentation, and compliance verification.
- Self‑Management: Proven ability to thrive in a remote setting, manage time effectively, and deliver high‑quality results independently.
Why Choose workpinnacle? – Career Growth, Learning, and Benefits
Professional Development: workpinnacle allocates an annual learning budget for certifications, conferences, and online courses. You’ll have access to internal mentorship programs, technical lunch‑and‑learn sessions, and a library of cutting‑edge resources to keep your skill set future‑ready.
Career Pathways: Starting as a Senior Windows Systems Engineer opens doors to roles such as Lead Automation Architect, Cloud Infrastructure Manager, or DevOps Engineering Director. Our transparent promotion framework rewards impact, initiative, and continuous learning.
Competitive Compensation: We offer a market‑aligned salary, performance‑based bonuses, and equity participation options for eligible employees. While exact figures vary by experience, you can expect a package that reflects the high demand for your expertise.
Comprehensive Benefits: Full‑time medical, dental, and vision coverage, 401(k) matching, generous paid time off, parental leave, and a flexible work‑from‑home stipend for home‑office equipment.
Inclusive Culture: workpinnacle is an Equal Opportunity Employer that celebrates the strength diversity brings to the workplace. We actively encourage applications from individuals with disabilities, protected veterans, and under‑represented groups. Our employee resource groups (ERGs) foster community, mentorship, and advocacy across the organization.
Work Environment & Culture at workpinnacle
Our remote‑first philosophy means you can work from anywhere in the world while staying tightly connected to a collaborative, high‑performing team. We use modern communication platforms, virtual whiteboards, and regular video stand‑ups to keep the energy high and the information flowing. The Web Systems Engineering team, comprised of 29 seasoned engineers, operates with a flat hierarchy, encouraging every voice to be heard. We celebrate wins together, learn from challenges, and continuously iterate on our processes to stay ahead of industry trends.
Compensation, Perks, and Benefits – A Snapshot
- Base Salary: Competitive, commensurate with experience and market benchmarks.
- Performance Bonus: Quarterly bonuses tied to individual and team achievements.
- Equity Options: Stock grants for eligible employees, aligning your success with workpinnacle’s growth.
- Health & Wellness: Comprehensive medical, dental, vision, and mental‑health resources.
- Retirement Planning: 401(k) with company match up to 5 % of salary.
- Learning Stipend: Annual budget for certifications, courses, and conferences.
- Remote Work Support: Home‑office allowance, high‑speed internet reimbursement, and ergonomic equipment.
- Paid Time Off: Generous vacation, sick leave, and holidays, plus unlimited PTO for senior staff.
- Community & Belonging: ERGs, virtual social events, and volunteer‑time‑off programs.
How to Apply – Take the Next Step with workpinnacle
If you are ready to bring your Windows systems expertise, automation passion, and cloud‑native mindset to a forward‑thinking, remote‑first organization, we want to hear from you. Please submit your updated resume, a cover letter highlighting your most relevant automation projects, and links to any public GitHub repositories or code samples that demonstrate your scripting and infrastructure‑as‑code capabilities.
Our recruitment team will review applications on a rolling basis, and qualified candidates will be invited to a virtual interview process that includes technical assessments, a culture fit conversation, and a final discussion with senior leadership.
Join workpinnacle – Shape the Future of Cloud Automation
Don’t miss this opportunity to accelerate your career while contributing to industry‑leading infrastructure solutions. At workpinnacle, your work matters, your growth is supported, and your voice is valued. Apply today and become a pivotal part of a team that’s building the next generation of automated, secure, and scalable Windows environments.
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