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Jonas Software

Long-term ownership of vertical software

Lead Systems Engineer

System AdministrationConfirmed live in the last 24 hours
Full-timeMarkham, ON, CanadaCA$110k

About the Job

Requirements

  • A bachelor's degree in Computer Science, Information Technology, or equivalent professional experience.
  • 5–7+ years of progressive experience in enterprise systems engineering and infrastructure administration.
  • Strong hands-on experience with Microsoft 365, including Exchange Online, Teams, and SharePoint Online.
  • Strong hands-on experience with identity and endpoint management, including Entra ID, Active Directory, Group Policy, and Intune.
  • Strong hands-on experience with Microsoft Azure, hybrid cloud environments, and SaaS/IaaS technologies.
  • Strong hands-on experience with Windows Server, DNS, DHCP, virtualization, and enterprise networking fundamentals.
  • Strong hands-on experience with patch management, infrastructure hardening, backup and recovery, disaster recovery, and monitoring.
  • Strong hands-on experience with PowerShell scripting, APIs, and infrastructure automation.
  • Ability to design, implement, and troubleshoot complex infrastructure solutions.
  • Experience leading technical projects, evaluating technology solutions, and working with vendors.
  • Ability to work independently, manage competing priorities, and collaborate across teams.

Responsibilities

  • Design, implement, and maintain secure, scalable, and resilient enterprise infrastructure solutions.
  • Lead infrastructure modernization initiatives, technology evaluations, proof-of-concept testing, and technical implementations.
  • Translate business requirements into practical, cost-effective technology solutions.
  • Establish technical standards, architecture documentation, and operational runbooks.
  • Identify emerging technologies and opportunities to improve infrastructure performance and efficiency.
  • Engineer and support Microsoft 365, Azure, Entra ID, Intune, Active Directory, and Windows Server environments.
  • Manage, secure, and optimize cloud environments across AWS and Microsoft Azure, including compute, storage, databases, networking, and connectivity.
  • Implement identity and access management, least-privilege security, governance, and compliance practices.
  • Ensure cloud performance, availability, and resilience through proactive monitoring, troubleshooting, automated backups, and disaster recovery planning.
  • Drive cloud cost optimization, resource efficiency, and infrastructure automation using Infrastructure as Code tools such as Terraform and native cloud deployment solutions.
  • Manage hybrid cloud infrastructure, identity services, endpoint management, and SaaS integrations.
  • Optimize infrastructure availability, performance, security, and operational costs.
  • Support enterprise backup, disaster recovery, and business continuity capabilities.
  • Incorporate security practices, compliance requirements, and risk management into infrastructure solutions.
  • Drive automation using PowerShell, APIs, and modern infrastructure management tools.
  • Identify and remediate infrastructure vulnerabilities, performance issues, and technical debt.
  • Improve operational efficiency through standardization, proactive monitoring, and continuous improvement.
  • Evaluate emerging technologies, including AI-enabled IT operations and intelligent automation, where appropriate.
  • Serve as a Level III escalation point for complex infrastructure and enterprise technology issues.
  • Lead technical troubleshooting, root cause analysis, and resolution of critical incidents.
  • Provide technical guidance and mentorship to fellow engineers and IT team members.
  • Collaborate with cybersecurity teams, business stakeholders, and technology vendors.
  • Lead infrastructure projects from design through implementation and operational handoff.
  • Participate in an on-call rotation and perform occasional after-hours maintenance as required.
  • Travel approximately 5–10%.

Desired Qualifications

  • Experience with AWS, VMware, Hyper-V, SAN/NAS storage, or NetApp.
  • Familiarity with SQL Server, MySQL, and Apple/macOS environments.
  • Experience with Infrastructure as Code tools such as Terraform or Bicep.
  • Knowledge of Microsoft Defender, security monitoring, and ITIL practices.
  • Relevant Microsoft Azure or Microsoft 365 certifications.
  • Exposure to AI-enabled infrastructure management and automation.

About the Company

Jonas Software

Long-term ownership of vertical software

Jonas Software manages a decentralized portfolio of over 160 independently run software companies across more than 40 vertical markets. It buys vertical market software (VMS) businesses and holds them long-term, allowing each company to keep its brand, leadership, and culture while Jonas provides capital, strategic oversight, and financial stability. Revenue comes from the ongoing operations of the portfolio’s companies, with the model focusing on deep industry expertise in nich es rather than restructuring or selling. Goal: grow value across the portfolio by supporting stable, niche-focused software companies for the long term, maintaining ownership stability instead of pursuing quick flips.

Company size
1,001-5,000
Company stage
Not listed
Total funding
Not listed
Headquarters
Toronto, Canada
Founded
1990

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