Windows System Administrator (TravelTech)

Company Background

Our client is an award-winning travel company that connects travelers with a nationwide network of independent travel advisors. Founded in 2010 and headquartered in the United States, the company combines innovative technology, personalized service, and strong supplier partnerships to deliver customized vacation experiences. By blending online convenience with professional expertise, the platform helps customers plan cruises, all-inclusive resorts, tours, and custom trips with confidence and value.

Project Description

The specialist will support a fragile legacy infrastructure environment while the organization continues building a new Azure/AKS-based platform. The role is focused on stabilizing Windows Server and Microsoft SQL Server-based systems, investigating infrastructure and performance issues, and providing an independent expert perspective during critical production incidents. The main value of the specialist is deep legacy infrastructure expertise, strong troubleshooting skills, and the ability to operate effectively in complex environments with limited documentation.

Technologies

• Windows Server
• Microsoft SQL Server
• IIS
• Networking: DNS, VPN, firewalls, routing
• Virtual machine infrastructure

What You'll Do

• Troubleshoot, support, and stabilize fragile legacy production systems;
• Investigate infrastructure, performance, and availability-related incidents;
• Analyze complex environments with limited documentation and identify operational risks, dependencies, and root causes;
• Provide an independent technical assessment and second opinion during critical incidents;
• Support Microsoft SQL Server-based applications and related infrastructure;
• Work closely with existing engineering teams while keeping the focus on operational stability and reliable production support;

Job Requirements

• 10+ years of experience in infrastructure, systems administration, DevOps, or production support;
• Strong experience with Windows Server environments;
• Deep knowledge of Microsoft SQL Server;
• Experience with IIS;
• Experience supporting virtual machine infrastructure;
• Hands-on experience with on-premises environments and legacy systems;
• Strong troubleshooting and root-cause analysis skills;
• Networking background, including DNS, VPNs, routing, firewalls, and connectivity troubleshooting;
• Experience diagnosing performance issues, latency problems, and infrastructure bottlenecks;
• English level: B2 or higher;

Nice To Have

• DBA background;
• Experience with legacy system modernization;
• Hybrid cloud experience;
• Basic Azure knowledge;

What Do We Offer

The global benefits package includes:

• Technical and non-technical training for professional and personal growth;
• Internal conferences and meetups to learn from industry experts;
• Support and mentorship from an experienced employee to help you professional grow and development;
• Health insurance;
• Sports activities to promote a healthy lifestyle;
• Flexible work options, including remote and hybrid opportunities;
• Referral program for bringing in new talent;
• Work anniversary program and additional vacation days.