Seasonal Data Entry & Windows Server Operations Manager – Remote IT Leadership Role at arenaflex

About arenaflex – A Global Retail & Technology Trailblazer

arenaflex is one of the world’s most recognised retailers, operating in more than a dozen countries and serving millions of customers every day. With a heritage built on value, quality, and a relentless focus on the customer experience, arenaflex has expanded its footprint far beyond the storefront, investing heavily in cutting‑edge technology to keep its supply chain, inventory, and digital platforms running flawlessly. Our IT organization is the engine that powers this mission, delivering secure, high‑availability services that enable seamless shopping, efficient logistics, and data‑driven decision‑making. As we continue to grow, we are looking for visionary leaders who can blend technical expertise with people‑first management to elevate our Windows Server environment and seasonal data entry operations.

Position Overview

arenaflex is seeking a seasoned Seasonal Data Entry & Windows Server Operations Manager to join our remote IT team. This full‑time, 45+ hour/week role blends hands‑on technical stewardship of Windows Server infrastructure with leadership of a high‑impact seasonal data entry team. You will be responsible for ensuring 24/7 uptime, security compliance, and performance optimization of our server ecosystem while guiding a dynamic group of data specialists through peak retail cycles.

Key Responsibilities

• Server Management & Architecture: Oversee the design, deployment, and maintenance of Windows Server environments across virtualized platforms (VMware, Hyper‑V). Ensure patch compliance, capacity planning, and performance tuning to meet service‑level agreements.
• Incident & Problem Management: Lead the resolution of high‑severity incidents, conduct root‑cause analyses, and implement preventative measures to minimize downtime.
• Security & Compliance: Enforce security baselines (e.g., CIS, NIST), manage Active Directory, Group Policy, and implement HIPAA‑aligned controls where applicable.
• Team Leadership: Supervise a crew of 10+ Windows Server administrators and seasonal data entry analysts. Conduct coaching sessions, performance reviews, and career‑development planning.
• Seasonal Data Operations: Direct the seasonal data entry workflow that supports inventory, pricing, and rebate programs during peak periods. Ensure data accuracy, timeliness, and adherence to quality standards.
• Cross‑Functional Collaboration: Partner with Network, Security, Application Development, and Business Analytics teams to align infrastructure initiatives with broader business goals.
• Process Improvement: Identify automation opportunities (PowerShell, DSC, Azure Automation) to streamline server provisioning, monitoring, and reporting.
• Reporting & Documentation: Produce weekly service dashboards, compliance reports, and maintain comprehensive runbooks for all critical services.
• On‑Call Rotation: Participate in a 24/7 on‑call schedule, providing rapid response during off‑hours to sustain continuous operations.

Essential Qualifications

• Minimum 2 years of hands‑on experience managing Windows Server environments (Windows Server 2016/2019/2022) in enterprise settings.
• Proven leadership of teams of 5 + technical professionals, with a track record of fostering collaboration and high performance.
• Experience with virtualization platforms (VMware vSphere, Microsoft Hyper‑V) and configuration management tools (SCCM, PowerShell Desired State Configuration).
• Solid understanding of networking concepts, DNS, DHCP, TCP/IP, and firewall management.
• Demonstrated ability to work under pressure, prioritize tasks, and meet tight deadlines during seasonal spikes.
• Excellent verbal and written communication skills; ability to translate complex technical concepts for non‑technical stakeholders.
• Bachelor’s degree in Computer Science, Information Technology, or a related field (or equivalent practical experience).
• Eligibility to work in the United States; remote work from any U.S. location is accepted.

Preferred Qualifications & Experience

• Certifications such as Microsoft Certified: Windows Server Hybrid Administrator Associate, MCSE, or VCP‑DCV.
• Exposure to cloud services (Azure IaaS, AWS EC2) and hybrid cloud integrations.
• Background in retail technology operations or experience with large‑scale inventory/rebate data processing.
• Familiarity with ITIL processes, NOC/IOTC/SOC environments, and incident management tools (ServiceNow, Jira).
• Experience leading seasonal or project‑based teams through high‑volume data entry cycles.
• Knowledge of compliance frameworks (HIPAA, PCI‑DSS) and audit readiness.

Core Skills & Competencies

• Technical Acumen: Deep expertise in Windows Server, PowerShell scripting, and virtualization.
• Leadership & Mentoring: Ability to inspire, coach, and develop technical talent.
• Analytical Thinking: Strong problem‑solving skills, data‑driven decision making, and attention to detail.
• Communication: Clear, concise, and persuasive communication with executives, peers, and frontline staff.
• Adaptability: Comfortable navigating fast‑changing environments, especially during holiday and promotional periods.
• Customer‑Focus: Understanding of how IT services impact the end‑customer experience and business outcomes.

Career Growth & Learning Opportunities at arenaflex

arenaflex invests heavily in the professional development of its employees. As a manager in our IT division, you will have access to:

• Industry‑leading training platforms (Pluralsight, LinkedIn Learning) and tuition reimbursement for advanced certifications.
• Mentorship programs pairing you with senior technology leaders across global offices.
• Opportunities to lead cross‑regional initiatives, including migration to hybrid cloud architectures.
• Rotational assignments that expose you to e‑commerce, supply‑chain analytics, and data‑science collaborations.
• Regular career‑path reviews to chart a clear trajectory toward senior architect or director‑level roles.

Work Environment & Culture

arenaflex’s culture is built on three pillars:

• Integrity: We hold ourselves to the highest ethical standards, ensuring transparency in every decision.
• Collaboration: Our teams operate in a “one‑team” mindset, breaking silos to deliver seamless experiences for customers and partners.
• Innovation: Continuous improvement is celebrated. Employees are encouraged to experiment, share ideas, and drive change.

Even though the role is remote, you will be part of a vibrant virtual community. Weekly virtual coffee chats, quarterly in‑person meet‑ups (location‑based), and an internal social platform keep the team connected. Flexible work hours are offered, with core collaboration windows to align with global stakeholders.

Compensation, Perks & Benefits

arenaflex offers a competitive hourly wage ranging from $20 to $30, commensurate with experience and certification depth. In addition to base pay, you will receive:

• Performance‑based bonuses linked to service‑level achievements and project milestones.
• Comprehensive health, dental, and vision coverage for employees and eligible dependents.
• 401(k) plan with company matching up to 5% of salary.
• Generous paid time off, including holiday, vacation, and sick leave.
• Professional development stipend and full reimbursement for approved certifications.
• Employee assistance program, wellness resources, and virtual fitness memberships.
• Technology stipend for home office setup (monitor, ergonomic chair, high‑speed internet).

Application Process

Ready to lead arenaflex’s Windows Server and seasonal data teams? Follow these steps to apply:

1. Prepare an up‑to‑date resume highlighting your Windows Server, team‑leadership, and data‑entry experience.
2. Draft a concise cover letter outlining why you’re passionate about supporting a global retailer’s technology backbone.
3. Submit your application through the arenaflex careers portal (link below).
4. Qualified candidates will be invited to a virtual interview series, including a technical assessment and a leadership case study.
5. Successful applicants will receive an offer package and onboarding schedule within two weeks of the final interview.

Why Join arenaflex?

At arenaflex, you are not just maintaining servers—you are powering the shopping experience for millions of customers worldwide. Your work directly influences inventory accuracy, pricing integrity, and the overall reliability of our digital services. If you thrive in fast‑moving environments, love solving complex technical challenges, and enjoy coaching high‑performing teams, this is the role for you.

Take the next step in your career and become a pivotal part of arenaflex’s technology future.

Apply now and start your journey with arenaflex today!

Apply Now