System Administrator

Jobtailor; Massachusetts; On-site; USD 90,000 - 120,000; Full time

Job summary

Jobtailor in Massachusetts seeks a skilled Systems Administrator to lead migrations of enterprise SaaS applications to cloud infrastructure and manage Windows Server environments. You will implement Azure-based solutions, maintain SQL Server ecosystems, and document operational procedures for global teams.

This role emphasizes reliability, security, and continuous improvement, with after-hours support as needed and collaboration across regional time zones.

Qualifications

• Bachelor's degree in Computer Science, Information Technology, or a related field.
• 3-6 years of experience in systems administration, cloud operations, hosting environments, or related IT roles.
• Hands-on experience with Windows Server 2016, 2019, and newer versions.
• Working knowledge of Windows Roles and Features, particularly IIS.
• Experience supporting Microsoft SQL Server environments, including installation, backups, maintenance, and basic query execution.
• Experience working with cloud platforms, preferably Microsoft Azure.
• Understanding of networking fundamentals, routing concepts, and infrastructure components.
• Ability to interpret technical documentation and deploy enterprise applications according to documented procedures.
• Strong problem-solving skills and a customer-focused mindset.
• Excellent verbal and written communication skills in English.
• Experience supporting global teams across multiple regions and time zones preferred.
• Experience with identity and access management technologies, including Azure AD, ADFS, Okta, or other SSO solutions preferred.
• Experience with ticketing and support platforms such as Zendesk or similar service management tools preferred.

Responsibilities

• Lead and execute migrations of enterprise SaaS apps to modern cloud infrastructure.
• Install, configure, maintain, and upgrade enterprise software and supporting infrastructure.
• Provision and manage virtual machines, server configurations, system patching, antivirus, and related tasks.
• Partner with globally distributed teams to ensure deployments and service delivery.
• Develop and maintain technical documentation, procedures, and knowledge resources.
• Identify opportunities to improve efficiency, scalability, reliability, and operational excellence.
• Support performance, security, and reliability of enterprise environments.
• Provide occasional after-hours support as required by global client and team needs.

Skills

Cloud Operations

Windows Server Administration

Microsoft SQL Server Support

Azure Platform Experience

Identity and Access Management

Networking Fundamentals

Technical Documentation

Operational Procedures

Continuous Improvement

Education

Bachelor's degree in Computer Science

Tools

Azure AD

ADFS

Okta

Zendesk

Job description

• Lead and execute migrations of enterprise SaaS applications from legacy hosting environments to modern cloud infrastructure
• Install, configure, maintain, and upgrade enterprise software applications and supporting infrastructure
• Provision and manage virtual machines, server configurations, system patching, antivirus, and related operational tasks
• Partner with globally distributed teams to ensure successful deployments and ongoing service delivery
• Develop and maintain technical documentation, operational procedures, and knowledge resources
• Identify opportunities to improve efficiency, scalability, reliability, and operational excellence through continuous improvement initiatives
• Support the performance, security, and reliability of enterprise environments
• Provide occasional after-hours support as required by global customer and team needs

Requirements

• Bachelor's degree in Computer Science, Information Technology, or a related field
• 3-6 years of experience in systems administration, cloud operations, hosting environments, or related IT roles
• Hands-on experience with Windows Server 2016, 2019, and newer versions
• Working knowledge of Windows Roles and Features, particularly IIS
• Experience supporting Microsoft SQL Server environments, including installation, backups, maintenance, and basic query execution
• Experience working with cloud platforms, preferably Microsoft Azure
• Understanding of networking fundamentals, routing concepts, and infrastructure components
• Ability to interpret technical documentation and deploy enterprise applications according to documented procedures
• Strong problem-solving skills and a customer-focused mindset
• Excellent verbal and written communication skills in English
• Experience supporting global teams across multiple regions and time zones preferred
• Experience with identity and access management technologies, including Azure AD, ADFS, Okta, or other SSO solutions preferred
• Experience with ticketing and support platforms such as Zendesk or similar service management tools preferred
• Additional language skills are a plus

Core Competencies

Demonstrates expertise in leading enterprise SaaS migrations to cloud infrastructure, with a strong focus on systems administration, cloud operations, and operational excellence. Proficient in managing Windows Server environments and supporting global teams with effective communication and problem-solving skills.

Highest-signal resume keywords

• Cloud Operations
• Windows Server Administration
• Microsoft SQL Server Support
• Azure Platform Experience
• Identity and Access Management

Hard Skills

• Systems Administration
• Cloud Infrastructure Management
• Windows Server 2016
• Windows Server 2019
• Microsoft SQL Server
• IIS
• Networking Fundamentals
• Technical Documentation
• Operational Procedures
• Continuous Improvement

Soft Skills

• Problem-Solving
• Customer-Focused Mindset
• Verbal Communication
• Written Communication

Industry Keywords

• Enterprise SaaS Applications
• Legacy Hosting Environments
• Virtual Machines
• Service Delivery
• Global Teams

Tools & Technologies

• Azure AD
• ADFS
• Okta
• Zendesk