Windows System Administrator II

Vail Systems; Illinois; Hybrid; USD 88,400 - 123,700; Full time

Benefits offered by this job

Multiple medical, dental, and vision plan options

401(k) savings plan with company match

35 days total annual PTO

Annual Bonus Program

Paid maternity and paternity leave

Gym membership

Job summary

A progressive software development company is seeking a full-time Windows System Administrator to manage and maintain Windows-based servers and applications. The ideal candidate will have 3-5 years in systems administration, strong communication skills, and a thorough understanding of Windows systems, security patching, and networking concepts. This role includes flexible hybrid work arrangements and offers competitive compensation.

Qualifications

• 3-5 years in a systems administration role.
• Proficient in troubleshooting issues.
• Strong knowledge of Windows Server maintenance.
• Familiar with patch management and security tools.

Responsibilities

• Install, configure, and maintain Windows Server operating systems.
• Administer Active Directory and Group Policy.
• Troubleshoot and resolve system issues.
• Respond to Jira ticket submissions and emails.

Skills

Troubleshooting

Verbal communication

Written communication

Windows server setup

Knowledge of Windows system components

Knowledge of networking concepts

Scripting (PowerShell)

Education

Bachelor’s degree in Computer Science or related field

Tools

Active Directory

Jira

O365

Microsoft Entra ID

Job description

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This range is provided by Vail Systems. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

Base Pay Range

$88,400.00/yr - $123,700.00/yr

Who You Are

Vail Systems is seeking a Windows Administrator familiar with managing system administrations. As a Windows Administrator, you will be expected to monitor, maintain, and upgrade Windows-based servers and applications on the network. You would be responsible for third‑party software and applications for internal communication and troubleshooting issues that may occur with firewalls. This role is individually focused and supported by a team, as you will collaborate with other technical IT employees to accomplish project deliverables.

The ideal candidate will have a strong information technology/systems background to successfully maintain Windows infrastructure and operating system. The candidate will have knowledge of troubleshooting, security patching, networking, end‑point security, scripting, computer science, and datacenters. Additionally, the candidate will be self‑motivated, dependable, and detail oriented.

What You’ll Do

• Install, configure, and maintain Windows Server operating systems and related software.
• Troubleshoot and resolve system issues, including performance bottlenecks, system failures, and security vulnerabilities.
• Administer Active Directory, Group Policy, and other critical server roles and services.
• Troubleshoot and resolve issues submitted through the Jira ticketing system.
• Attend and provide status updates in weekly meetings.
• Respond to all incoming emails and Jira submissions.
• Administer third‑party software, such as O365, Sophos, Mimecast, and Veeam.
• Ensure timely installation of patches and updates to maintain system security and compliance standards, utilizing tools such as BigFix and WSUS.
• Administer Microsoft Entra ID (formerly Azure Active Directory).
• Document and update wiki pages with solutions identified from ticket requests.
• After‑hours deployments and maintenance as required.

Qualifications - We encourage you to apply if you think your experience may be a match, even if you do not meet all of the qualifications.

• 3-5 years of experience in a systems administration role.
• Experience with troubleshooting.
• Excellent verbal and written communication skills.
• Proficiency with Windows server setup, maintenance, and deployment.
• Knowledge of Windows system and components.
• Bachelor’s degree in Computer Science, IT, Information Systems, or related field, preferred.
• Familiarity with patch management and security tools, preferred.
• Familiarity with standard networking concepts (TCP/IP, Windows Networking, VPN, Firewalls), preferred.
• Knowledge of cloud access management solution Microsoft Entra ID (formerly Azure Active Directory), preferred.
• Experience with scripting tools (e.g. PowerShell, etc.), preferred.
Who We Are

At Vail, we believe in the unique power of voice interactions to create more expressive, more intimate, and more efficient interpersonal interactions. Using Vail technology, we make millions of voice interactions better every day. We process around 10% of all toll‑free call traffic in the U.S.; 1 in 10 times when someone calls a customer support hotline, Vail is routing or interacting with that call.

We are rapidly growing across multiple dimensions, including our customer base, the scope of products we offer, and the size of our team. Now is the right time for a strong candidate to join and grow with us. We have a supportive culture where employees are encouraged to achieve both personal and team goals because we believe growth leads to both business impact and personal fulfillment.

We offer competitive compensation and affordable benefits with flexibility and choice to meet individual and family (including Domestic Partnerships) needs, including:

• Multiple medical, dental, and vision plan options
• Company‑paid life insurance, short and long‑term disability
• 401(k) savings plan with company match (50% on first 6% of employee contribution)
• 35 days total annual PTO
• Annual Bonus Program
• Paid maternity and paternity leave
• Relocation allowance
• Employee referral bonus
• Gym membership
• Technical and Professional Development stipend

We are striving to implement and sustain an inclusive and equitable work environment for all employees by sourcing underrepresented groups and continually empowering those individuals within our organization to further enrich Vail’s communication solutions. We recognize that equitable and unique individuals benefit our teams’ problem‑solving, innovation, and development efforts.

Our offices are located in Deerfield and Chicago, IL. Interviews and onboarding are conducted in our offices when possible. We observe a hybrid work format that provides employees flexibility to collaborate with team members based on business needs.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

Seniority Level

Not Applicable

Employment Type

Full‑time

Job Function

Information Technology

Industries

Software Development

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Location: Pleasant Prairie, WI

Notice: This position is for a full‑time, Windows System Administrator.