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.

What You’ll Be Doing

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.

What You’ll Be Responsible For

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.

Systems, Integrations and New Digital Tools

• 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.

Security, Privacy and Accessibility

• 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 usage, system performance, open issues, project progress, risks, and recommended improvements.
• Use user feedback and system data to identify opportunities to improve digital services and program delivery.
• Stay current with relevant digital tools and technologies and recommend practical solutions that fit program needs.

Team and Vendor Coordination

• Work closely with Workforce Development, Communications, program leadership, and other internal teams to understand priorities and deliver technical support.
• Coordinate with external developers, hosting providers, software vendors, and other technical partners as required.
• Manage multiple requests and projects, maintain clear priorities, and provide timely progress updates.
• Support occasional program activities, events, or training sessions where on‑site technology assistance is required.

Tools and Systems You May Use

• Website content management systems and hosting platforms
• Website plugins and related digital resources
• Landscape.jobs and other online job‑bank tools
• Airtable, Jotform, online registration forms, and participant-facing portals
• CRM and program‑management platforms
• Google Analytics and related website tracking tools
• Google Workspace and Microsoft Office
• Virtual meeting, webinar, and online learning platforms

Requirements

• Demonstrated experience in IT support, web administration, digital operations, systems coordination, or a related role.
• Strong understanding of website content management systems, backend administration, plugins, integrations, and digital workflows.
• Experience troubleshooting websites, software, user‑access issues, online forms, and other technology platforms.
• Experience maintaining websites and supporting website launches, major updates, or post‑launch stabilization.
• Working knowledge of website analytics, performance monitoring, and tracking tools.
• Understanding of cybersecurity, privacy, access controls, data protection, and digital accessibility practices.
• Strong problem‑solving skills and the ability to assess issues, identify practical solutions, and elevate risks appropriately.
• Excellent communication skills, including the ability to explain technical information clearly to non‑technical users.
• Strong organizational and project‑management skills, with the ability to manage multiple requests, priorities, vendors, and deadlines.
• Ability to work independently, take initiative, document work clearly, and collaborate effectively across teams.
• Experience with CRM platforms, Airtable, job boards, Jotform, Google Workspace, or comparable systems is an asset.
• Experience working in a government‑funded, not‑for‑profit, association, workforce‑development, or training environment is an asset.
• Knowledge of Ontario’s landscape and horticulture sector is an asset but not required.

About this Position

• Full‑time, fixed‑term contract position through June 29, 2027, with the possibility of renewal.
• Salary: $60,000 - $65,000 per year.
• Includes vacation and personal time off, and health benefits.
• Reports to the Workforce Development Manager and Director of Digital Infrastructure. Works closely with Workforce Development leadership, Communications, program staff, and external technology vendors.
• Primarily in‑office, with some hybrid flexibility; based out of our office in Milton, ON.
• Some evening or weekend work may be required based on system launches, maintenance, program activities, or events.
• Occasional travel within Ontario may be required to support program delivery or events.
• A valid Ontario driver’s licence and access to reliable transportation are required.
• A beautifully renovated modern office space.
• A supportive, collaborative team environment.

About Landscape Ontario

About Landscape Ontario
Landscape Ontario Horticultural Trades Association is a provincial trade association representing approximately 3,000 members across the landscape horticulture sector. A not‑for‑profit, volunteer‑driven organization, we are dedicated to advancing the profession through leadership, education and collaboration. Landscape Ontario members design, build and maintain outdoor spaces that support healthy communities, environmental resilience and economic growth across Ontario. We are committed to building an inclusive and collaborative organization where everyone feels welcomed and valued, regardless of gender, race, nationality, orientation or ability.

Equal Opportunity & Accessibility

Landscape Ontario is committed to creating an inclusive, accessible and welcoming workplace. We encourage applications from individuals of all backgrounds, experiences and abilities.

In accordance with the Accessibility for Ontarians with Disabilities Act (AODA), accommodations are available throughout the recruitment and selection process. Applicants requiring accommodation are encouraged to advise us at any stage so that appropriate arrangements can be made.

Landscape Ontario complies with Ontario’s employment legislation regarding the use of artificial intelligence in recruitment. Artificial intelligence (AI) is not used to screen, assess or select applicants for this position.