IT Support & Digital Systems Specialist

Workforce Development Full Time Milton, ON $60,000 - $65,000 CAD per year

You are a practical, solutions-focused technology professional who enjoys keeping websites, digital platforms, and online services reliable and easy to use. You can troubleshoot issues, manage competing priorities, and explain technical information clearly to people with different levels of comfort with technology.

You are proactive about identifying risks, improving systems, and communicating progress. You work well independently and with program staff, communications teams, vendors, participants, and employers, and you understand the importance of security, accessibility, accuracy, and follow-through.

As the IT Support & Digital Systems Specialist, you will provide dedicated technical support for Landscape Ontario’s GROW and apprenticeship activities funded through Ontario’s Skills Development Fund. You will maintain and update project websites, support the online job bank, manage digital resources and website plugins, troubleshoot software and technology issues, and help ensure the reliable operation of online systems used by participants, employers, and project staff.

You will also support the implementation and integration of new digital tools, coordinate technical work with internal teams and external vendors, and help maintain secure, accessible, and user-friendly platforms that support program delivery and reporting.

Project Websites and Digital Platforms

• Maintain and update GROW, apprenticeship, job bank, and other SDF-related websites and digital platforms.
• Manage content updates, backend administration, website plugins, forms, links, redirects, and related digital resources.
• Test website functionality, monitor performance, and identify and resolve errors, broken features, usability issues, and integration problems.
• Ensure online information and tools remain accurate, accessible, reliable, and user-friendly.

Online Job Bank and User Support

• Provide technical and administrative support for the online job bank, including employer and job-seeker registration, job postings, templates, and user access.
• Respond to technical issues experienced by participants, employers, and staff using project websites, forms, portals, virtual platforms, and other online tools.
• Create clear instructions, resources, and basic training to help users and staff work effectively with program technology.
• Track recurring issues and recommend practical improvements to strengthen the user experience.

• Support integrations between project websites, online forms, databases, CRM tools, analytics platforms, and other program systems.
• Assist with selecting, configuring, testing, launching, and maintaining new digital tools that support program delivery.
• Coordinate technical requirements, timelines, testing, and issue resolution with internal teams and external vendors.
• Maintain clear documentation of system configurations, integrations, workflows, changes, and troubleshooting procedures.

• Apply appropriate security, privacy, access-control, and data-protection practices across project platforms and digital resources.
• Monitor website plugins, integrations, user permissions, and third-party tools for updates, risks, and required action.
• Support compliance with organizational, funder, privacy, accessibility, and government digital requirements.
• Escalate security incidents, privacy concerns, service disruptions, and significant technology risks promptly.

Monitoring, Analytics and Continuous Improvement

• Support the setup and maintenance of website analytics, tracking tools, tags, and performance monitoring.
• Prepare clear updates on website…