Remote Windows Automation Engineer – Jenkins Pipeline & Ansible Playbook Specialist for arenaflex Infrastructure (Contract‑to‑Hire, Fully Remote)

About arenaflex

arenaflex is a fast‑growing leader in the technology‑enabled services space, empowering businesses worldwide with the tools they need to modernize, automate, and scale their critical IT operations. With a culture built on curiosity, inclusivity, and continuous learning, arenaflex invests heavily in cutting‑edge open‑source technologies and cloud‑native solutions to keep its customers ahead of the competition. As part of our commitment to innovation, we are expanding a dedicated Web Systems Engineering team that delivers resilient, automated infrastructure for Windows environments across public clouds.

Why Join arenaflex?

• Impactful Work: Directly influence the reliability and performance of mission‑critical Windows services used by thousands of end‑users.
• Remote‑First Flexibility: Work from any location with a reliable internet connection—no commuting, no relocation hassles.
• Open‑Source Focus: Contribute to real‑world implementations of Ansible, Terraform, Jenkins, and other community‑driven tools.
• Career Acceleration: A clear contract‑to‑hire pathway that can lead to a permanent senior engineering role based on performance.
• Inclusive Culture: arenaflex is an equal‑opportunity employer that celebrates diversity, supports veterans, and provides accommodations for individuals with disabilities.

Role Overview

We are seeking a highly motivated Windows Automation Engineer to join our 29‑person Web Systems Engineering team. In this role you will design, develop, and maintain automation pipelines that provision, configure, and manage Windows Server environments on Azure and Google Cloud Platform (GCP). You will collaborate closely with senior engineers, product owners, and external consultants to replace legacy tooling with modern, open‑source solutions, specifically focusing on Jenkins pipelines and Ansible playbooks for Windows OS provisioning.

Key Responsibilities

• Design, implement, and optimize Jenkins pipelines that build, test, and deploy Windows workloads across multiple cloud environments.
• Create, maintain, and troubleshoot Ansible playbooks and Terraform modules that automate Windows Server provisioning, patching, and configuration drift detection.
• Develop and enforce PowerShell best practices, ensuring scripts are modular, reusable, and version‑controlled in GitHub.
• Partner with the infrastructure security team to embed compliance checks (e.g., CIS Benchmarks) into automated workflows.
• Provide tier‑2 support for automation failures, performing root‑cause analysis and recommending improvements.
• Document all automation solutions, runbooks, and architectural decisions in a clear, searchable knowledge base.
• Mentor junior team members on Windows automation concepts, Git workflows, and cloud‑native tooling.
• Continuously evaluate emerging open‑source technologies, proposing upgrades that increase efficiency and reduce operational cost.
• Collaborate with external consultants and stakeholders to ensure smooth migration from proprietary tools (e.g., vRealize Automation) to our new open‑source stack.

Essential Qualifications

• Minimum 5 years of hands‑on experience administering Windows Server (2016/2019/2022) in production environments.
• Proficient in PowerShell scripting, with a portfolio of publicly available GitHub repositories or work samples demonstrating automation expertise.
• Strong understanding of public cloud platforms—especially Azure and GCP—including networking, identity, and resource management.
• At least 4 years of experience writing automation scripts with open‑source tools such as Ansible and Terraform. Preference given to candidates with Ansible playbook experience for Windows nodes.
• Proven track record of supporting and extending Jenkins pipelines that integrate with Windows provisioning workflows.
• Demonstrated ability to produce clean, maintainable code and to showcase it via GitHub or comparable version‑control platforms.

Preferred (But Not Mandatory) Skills

• Certifications such as Microsoft Certified: Azure Administrator Associate, Google Cloud Professional Cloud Architect, or Red Hat Ansible Automation Engineer.
• Experience with containerization technologies (Docker, Kubernetes) on Windows nodes.
• Familiarity with IaC testing frameworks (e.g., Molecule, Terratest).
• Knowledge of security hardening standards (CIS, DISA STIG) for Windows servers.
• Background in continuous‑delivery concepts and DevSecOps practices.

Core Competencies & Soft Skills

• Analytical Mindset: Ability to dissect complex automation failures and develop systematic solutions.
• Collaboration: Comfortable working in a geographically distributed team, sharing knowledge, and seeking feedback.
• Communication: Clear written documentation and concise verbal explanations for both technical and non‑technical audiences.
• Self‑Direction: Proactively manage workload, set realistic timelines, and own deliverables in a remote environment.
• Adaptability: Thrive in a fast‑changing tech stack, embracing new tools, languages, and methodologies.

Career Growth & Learning Opportunities

arenaflex is committed to the professional development of its engineers. In this role you will:

• Gain deep expertise in Windows automation across both Azure and GCP, a rare and highly marketable skill set.
• Earn access to a corporate learning budget for certifications, online courses (Pluralsight, Udemy, A Cloud Guru), and conference attendance (e.g., AnsibleFest, Microsoft Ignite).
• Participate in internal “Tech Talks” where engineers share innovative solutions and lessons learned.
• Potentially transition to a senior or lead engineering position after successful contract conversion, with expanded responsibilities for architecture and team mentorship.
• Collaborate with cross‑functional product teams, opening pathways to product management or solutions engineering tracks.

Work Environment & Culture at arenaflex

Our team operates on a hybrid of async and real‑time collaboration tools (Slack, Microsoft Teams, Confluence, and Jira). We value results over “clock‑watching” and trust our engineers to deliver high‑quality work while balancing personal life. Key cultural pillars include:

• Diversity & Inclusion: We celebrate unique perspectives and actively support underrepresented groups in tech.
• Transparency: Regular all‑hands meetings, open‑door leadership, and a clear roadmap are shared with every team member.
• Innovation Time: Engineers receive dedicated hours each month to experiment with new tools or pursue passion projects.
• Recognition: Monthly “Spotlight Awards” highlight outstanding contributions, with gift cards, swag, and shout‑outs.

Compensation, Perks & Benefits

arenaflex offers a competitive salary range aligned with market benchmarks for remote Windows automation specialists. In addition to base pay, you will receive:

• Performance‑based bonuses tied to project milestones and automation efficiency gains.
• A comprehensive health‑care package (medical, dental, vision) with options for employee‑only or family coverage.
• Retirement savings plan with employer matching contributions.
• Generous paid time off (PTO) policy, plus sick days and mental‑health days.
• Home office stipend for ergonomic furniture, monitors, and high‑speed internet.
• Access to a global employee assistance program (EAP) for counseling and wellness resources.
• Remote‑work travel allowance for occasional in‑person team gatherings or conferences.

Contract Details & Start Timeline

This is an initial contract position running through the end of the calendar year, with a strong possibility of conversion to a permanent role and extensions based on performance. The successful candidate will be expected to begin work within two weeks of receiving an offer, with interview rounds scheduled as early as next week. The contract offers a blended rate that reflects both the seniority of the role and the remote nature of the work.

How to Apply

If you are ready to take charge of Windows automation at a forward‑thinking organization, we want to hear from you. Click the link below to submit your résumé, a brief cover letter, and any GitHub repositories or code samples that demonstrate your automation expertise.

Apply Now – Join the arenaflex Automation Team!

Take the Next Step with arenaflex

At arenaflex, your technical talent will be celebrated, your growth will be supported, and your contributions will directly shape the future of enterprise automation. Don’t miss this chance to work with a talented, diverse team while enjoying the freedom of remote work. Apply today and become a cornerstone of our Windows automation journey.