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System Administrator Microsoft Windows Server & Security

Activo Inc.
Full Timemid
Markham, Ontario, CAPosted March 5, 2026

Job Description

About the Company:

Activo is a leading network systems integrator and national IP infrastructure company that provides network systems planning, integration, installation, and support services across Canada. We design and build IP networks that converge systems, allowing you to take full advantage of emerging innovations with future-ready infrastructures.

About the Role

Job Title: System Administrator – Microsoft Windows Server & Security

Position: Contract 6 months (with possibility of Full‑Time Employment)

Rate: $70 per Hour

Position Summary

We are seeking a System Administrator with ten (10+ years) of hands-on experience administering on-premise Microsoft Windows Server environments and Windows-based endpoints in enterprises or complex IT environments.

The successful candidate must have deep expertise in Microsoft Server operating systems, Active Directory, authentication protocols, identity hardening, and Windows security controls, with a strong focus on securing enterprise infrastructure and reducing identity-based attack surfaces. This role requires a seasoned professional who understands not just how Windows systems work, but how they fail, how they are attacked, and how to harden them correctly.

The successful candidate will be joining a dynamic team of resources with a wide breadth of experience and skills who will strive to enable and assist each other to succeed. With the goal of providing excellent service while touching on many different technologies.

Responsibilities

The successful candidate will be required to work on several internal projects while also providing direct support to internal customers as outlined below.

Projects and Regular Responsibilities:

Windows Server & Platform Administration

  • Design, administer, and maintain secure on-premises Microsoft Windows Server environments in on-premises enterprise settings.
  • Provide advanced administration and security oversight of core Windows services, including directory services, web services, file services, authentication, and enterprise client platforms.

Identity & Authentication Security

  • Lead Active Directory and identity security initiatives aligned with industry best practices.
  • Govern the design, configuration, and lifecycle of privileged and service identities.
  • Design and enforce secure authentication and directory communication standards.
  • Continuously evaluate and improve authentication protocols, cryptographic configurations, and session controls.
  • Maintain authentication ticketing and session lifetime settings aligned with organizational security policy.

Windows Hardening & Privileged Access

  • Implement and maintain operating system–level security protections for credentials, privileged processes, and administrative access paths.
  • Design and enforce secure file‑sharing and access control models based on least privilege.
  • Partner with security governance teams to validate platform hardening standards.

Application & Service Security

  • Secure and manage application and service identities, permissions, and runtime configurations.
  • Administer and harden IIS and database service environments in accordance with approved security baselines.
  • Ensure enterprise applications follow security best practices for authentication, authorization, and service isolation.

Other Responsibilities

  • Work on a flexible schedule to support internal ad-hoc support responsibilities, and the maintenance or implementation work that will be required out of standard business hours (as an example, Upgrade or patching work resulting in potential risk or outage will be required to be performed during maintenance windows, generally overnights on weekends).
  • Perform administrative tasks within the VMware environment (moves, adds, changes, basic provisioning)
  • Manage/maintain on-premises Server 2019/2022 devices, upgrading from Server 2019 was feasible.
  • Perform troubleshooting, upgrades and patching of Windows environments where applicable
  • Provide support on an ad-hoc basis to internal customers when service issues arise that tier 1 service desk is unable to resolve
  • Collaborate with other team members on MS, BUDR and VMware solutions were applicable
  • Regularly communicate answers to complex questions and respond to detailed inquiries about technical issues and how to resolve them.
  • Be capable of working effectively and efficiently with support from other members of the engineering team.
  • Effectively coordinate, install and manage multiple projects.
  • Be responsible for successfully completing assignments on time and within budget
  • Maintain complete and accurate project documentation and records of all activities, licenses etc.
  • Other duties as required.

Must have:

  • 10+ years of hands-on experience with on-premises Microsoft Windows Server administration.
  • Extensive experience managing on-premises enterprise Active Directory environments.
  • Proven experience securing authentication protocols and identity infrastructure (on premises).
  • Proven experience with on-premises Windows Servers, specifically pertaining to:
  • Privileged account and service account security
  • Service Principal Names (SPNs)
  • LDAP signing and channel binding
  • Windows RPC authentication
  • NTLM authentication protocol
  • Kerberos authentication hardening (including AES-based encryption)
  • TGT lifetime management
  • MSSQL service permissions
  • LSASS and Credential Guard
  • SMB signing and SMB share permissions
  • IIS administration and security
  • Expert knowledge of Microsoft Server technologies and best practices
  • Must have extensive experience in performing advanced configuration of Microsoft Server infrastructures, including Exchange, Active Directory, Group Policy, Domain Controllers, DNS, IIS, SSL Certificates, and multi–Domain Controller environments
  • Excellent skills with VMware and SAN administration
  • Must have excellent problem solving and troubleshooting skills with the ability to perform advanced troubleshooting on Microsoft, VMware, Storage technologies.
  • Must have experience in performing upgrades and installations of Servers, Storage Devices (SANS), iSCSI technologies (for example, upgrading firmware, replacement of components, and configuration of devices)
  • Proficient in the support and use of Microsoft Office solutions (Outlook, Excel, and Word)
  • Proficiency and significant experience in developing, administering, and troubleshooting Backup Disaster and Recovery solutions
  • Demonstrated proficiency in IP Networking and the TCP/IP stack
  • Exceptional customer service, written, verbal and interpersonal skills.
  • Exceptional documentation skills (Visio Diagrams, Ticket Entry report of completed tasks, and Technical Change Requests)
  • Maintain a professional attitude and appearance at all times

Nice to have

  • Proficiency and experience with Datto Backup and Recovery
  • Proficiency and experience with Linux or Unix environments
  • Proficiency and experience with Linux or Unix DNS, SSL Certificates, administration, upgrades, and troubleshooting

Certifications:

The ideal candidate will have several years of experience with the above technologies and several of the following certifications, or equivalent knowledge. However, current MCSE in on- premise server infrastructure and verifiable administrative experience with VMware are a requirement for application.

MCSE for Server or Communications, MSCA Server or Desktop, VCP, VCAP, VMCE, CCNA, Network+, Server+, Storage+, A+

Activo is an equal opportunity employer committed to an inclusive and accessible workplace. If you require accommodation or accessible formats/communication supports during the hiring process, please let us know – we will work with you to ensure your needs are met.

Job Types: Full-time, Fixed term contract

Contract length: 6 months

Pay: $70.00 per hour

Expected hours: 40 per week

Benefits

  • Company events
  • On-site parking

Experience

  • System administration: 10 years (required)

Licence/Certification:

  • MCSA (preferred)
  • CCNA (preferred)
  • MCSE (required)

Work Location: In person

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