Windows Engineer – Server Upgrades

About MatchPoint Solutions

MatchPoint Solutions is a fast-growing global IT and Engineering services firm delivering innovative technology solutions to leading enterprises including Uber Robinhood Netflix Airbnb Google and more. With a growing international presence across North America Europe Asia and South America we help organizations turn ideas into outcomes through cutting-edge technology industry best practices and deep technical expertise.

Were expanding our team and looking for driven professionals who want to build impactful solutions in a collaborative high-growth environment.

Job Title: Windows Engineer Server Upgrades

Location: Remote

Duration: 2 Months

Employment Type: Contract

Pay Rate Range: $75 to $80

Responsibilities:

• Plan schedule and execute Windows Server upgrades (in-place upgrades migrations reboots) across enterprise environments.
• Perform upgrades for servers in production (80%) and non-production (20%) coordinating maintenance windows-many after business hours (PT).
• Validate pre-upgrade readiness: backups capacity application compatibility patch level and rollback plans.
• Perform post-upgrade verification health checks performance tuning and remediation.
• Create and follow change management processes submit change requests and coordinate approvals with application owners IT operations and business stakeholders.
• Work closely with application teams database teams virtualization (VMware/Hyper-V) storage and networking to ensure compatibility and minimize service disruption.
• Develop and run automation and tooling (PowerShell CI/CD) to standardize upgrade tasks and reduce manual risk.
• Maintain clear documentation: runbooks upgrade plans rollback procedures and post-change reports.
• Ensure compliance with healthcare regulatory and security requirements (HIPAA encryption access controls) during upgrades.
• Troubleshoot and resolve issues during and after upgrades; provide on-call or after-hours support as needed for scheduled windows.
• Participate in capacity planning lifecycle management and server decommissioning when applicable.
• Contribute to continuous improvement of upgrade processes testing frameworks and operational readiness.

Required Qualifications:

• 5 years experience administering and upgrading Windows Server environments (2012R).
• Hands-on experience with in-place upgrades migrations and build/configuration of Windows servers.
• Strong PowerShell scripting skills for automation and orchestration.
• Familiarity with virtualization platforms (VMware vSphere Microsoft Hyper-V) and systems integration.
• Experience with backup/restore solutions and validation (Veeam NetBackup or similar).
• Comfortable performing after-hours/maintenance-window work (Pacific Time).
• Excellent change management troubleshooting and incident response skills.
• Ability to coordinate across cross-functional teams and communicate clearly with technical and non-technical stakeholders.
• Knowledge of healthcare IT compliance security controls and requirements (HIPAA logging auditing).
• Strong documentation skills and attention to detail.

Preferred Qualifications:

• Experience with configuration management and IaC tools (Ansible Terraform).
• Familiarity with Active Directory DNS and Group Policy at enterprise scale.
• Experience with monitoring/observability tools (SCOM Prometheus Datadog).
• Certifications such as Microsoft Certified: Windows Server Azure Administrator or relevant VMware certifications.
• Prior experience in healthcare or regulated environments.

Equal Employment Opportunity

MatchPoint Solutions is an equal opportunity employer. We are committed to providing equal employment opportunities to all employees and applicants and do not tolerate discrimination or harassment of any kind. Employment decisions are made without regard to race color religion age sex national origin disability genetic information protected veteran status sexual orientation gender identity or expression or any other characteristic protected by applicable federal state or local laws.

This policy applies to all aspects of employment including recruitment hiring placement promotion termination layoffs recall transfers leaves of absence compensation and training.