IT Manager

Job Description:

About WinePOS

WinePOS is a growing software company building products for the wine and beverage industry. We are a subsidiary of Jonas Software, and our technology stack includes cloud and on prem applications.

Role Summary

Manage endpoint security, vulnerability management, SIEM monitoring, identity and access administration, DNS/email security, secure remote access, and IT operations across Windows, Mac, and selected Linux systems.

What You'll Do

Build the IT Foundation

• Implement formal onboarding and offboarding processes for employee accounts and equipment across all company systems
• Own an IT help desk and ticketing system for support requests
• Own asset management platform to track all company hardware (laptops, desktops, servers, network equipment)
• Deploy and manage an MDM solution across all company endpoints (Windows and Mac)
• Maintain IT policies and documentation covering security, access management, acceptable use, and incident response
• Perform periodic access reviews to ensure proper permissions across all systems

Endpoint & Network Management

• Manage the office LAN, firewall, switches, and internet connectivity
• Evaluate and upgrade network equipment as needed
• Deploy and manage endpoint security software across all company devices
• Enforce disk encryption on all endpoint devices
• Monitor and manage endpoint patching and OS updates
• Manage DNS and email security configurations.

Security & Compliance

• Monitor the Rapid7 SIEM for security events and respond to alerts
• Enforce MFA across all company systems
• Maintain least-privilege access controls across all platforms
• Manage privileged access with segregated administrative accounts
• Conduct periodic vulnerability assessments and remediate findings
• Maintain an incident response plan and disaster recovery plan, including annual tabletop exercises
• Perform regular internal security audits (exposed services, misconfigurations, EOL software)
• Coordinate with engineering team on server-side security items (agent deployment, hardening, log ingestion)

Access & Account Management

• Manage core business systems, collaboration suite, and remote-access systems
• Manage password manager administration (vaults, sharing policies, permissions)
• Manage secure remote access
• Manage physical office access control (implement and maintain an electronic access system)
• Ensure timely provisioning and deprovisioning tied to employee lifecycle events
• Oversee backup strategy -- ensure backups are encrypted and regularly tested for restoration

End-User Support

• Provide technical support to approximately 30 employees across Windows and Mac platforms
• Support both in-office and remote employees (approximately 50/50 split)
• Troubleshoot hardware, software, network, and connectivity issues
• Provide patient, clear guidance to less technical staff while respecting the autonomy of technical team members
• Set up and configure new employee workstations and laptops

Required Qualifications

• 3+ years of experience in IT systems administration or a similar hands-on IT role
• Experience administering Windows and macOS endpoints in a business environment
• Experience with Google Workspace administration (user management, security settings, organizational units)
• Hands-on experience with network administration (firewalls, switches, VPN configuration)
• Experience deploying and managing endpoint security tools (EDR/antivirus, vulnerability scanners)
• Understanding of identity and access management principles (least privilege, MFA, SSO, access reviews)
• Comfortable working in Linux environments (Debian/Ubuntu) for tasks like deploying agents, reviewing logs, and basic troubleshooting
• Familiarity with MDM/endpoint management platforms
• Strong troubleshooting skills across hardware, software, and networking
• Ability to communicate technical concepts to non-technical users with patience
• Self-directed with the ability to prioritize and manage multiple concurrent projects independently

Preferred Qualifications

• Experience with enterprise EDR, vulnerability management, and SIEM tooling
• Experience writing and implementing IT security policies and procedures
• Experience with IT compliance audits (ITGC, SOC 2, or similar)
• Experience with endpoint management platforms
• Experience with cloud platforms
• Experience implementing physical access control systems (key card/fob or biometric)
• Experience building IT operations from scratch in a small company environment
• Relevant certifications (CompTIA Security+, CISSP, or similar) are a plus but not required

What Success Looks Like

• 30 days: Solid understanding of the environment, critical security gaps addressed, onboarding/offboarding process in place
• 90 days: MDM deployed, ticketing system operational, security tooling fully deployed across all endpoints, access reviews established
• 6 months: All IT policies documented and in practice, backup strategy modernized, incident response and disaster recovery plans current and tested
• 12 months: Mature, well-documented IT operations; clean compliance posture; proactive security monitoring; employees supported efficiently regardless of technical skill level

Why This Role

• Your work directly protects the company and makes every employee's day smoother.
• Enterprise security tooling already licensed. Leadership is invested in doing this right.
• You report to company leadership with full authority to make decisions and recommend solutions.
• A strong engineering team handles application servers and infrastructure, so you can focus on what matters most -- security, endpoints, and operations.

Business Unit:

Innovative Computer Solutions Inc

Scheduled Weekly Hours:

40

Number of Openings Available:

1

Worker Type:

Regular

                                                                               

More About Jonas Software:

Jonas Software is a leading provider of enterprise management software solutions, serving a wide range of vertical markets including hospitality, healthcare, construction, education, personal care, fitness, leisure, moving and legal services, to name a few. Within these markets, Jonas is comprised of over 65 distinct brands, each a respected leader in its domain.

 

Jonas’ vision is to be the branded global leader across these verticals and to be recognized by customers and industry stakeholders as the trusted provider of “Software for Life.” We are committed to technology, product innovation, quality, and exceptional customer service.

 

Jonas Software supports over 60,000 customers in more than 30 countries. We employ over 6,000 skilled professionals, including industry experts and technology specialists. Across our broader network, we support a global workforce of more than 30,000 employees.

 

Headquartered in Canada, Jonas Software has a global footprint with offices around the world. We’re a 100% owned subsidiary of Constellation Software Inc., based in Toronto, publicly listed on the TSX (CSU.TO), and a member of the S&P/TSX 60 Index.