📍Location: Anywhere On Side has a branch
🕒Employment Type: Full-Time/Permanent
📅 Posting Date: August 24, 2026
Position Summary
The Application Support Specialist is a key member of the IT team, ensuring the business applications our crews and support teams rely on every day are secure, reliable, and running at their best. As the subject matter expert for assigned applications, you’ll provide technical support, troubleshoot issues, collaborate with stakeholders, and identify opportunities to improve systems and processes across the business.
Working closely with internal teams and external vendors, you’ll help deliver technology solutions that support operational excellence, drive efficiency, and enable a great user experience.
(This posting reflects an existing vacancy)
Compensation
- Salary Range: $80,000-$90,000
- Salary based on skills, qualifications and experience
- Annual Performance Incentive Bonus – Percentage of base salary subject to personal and company performance.
Benefits
- Extended health coverage (medical, dental, vision, etc.)
- Employee assistance program (EAP)
- Group RRSP, with company matching DPSP
- Life and disability insurance
- Opportunities for advancement and internal mobility
What You’ll Do
- Application Operations & Support: Serve as the senior technical professional and primary SME for business-critical applications. Troubleshoot complex application issues across integrated environments to ensure minimal operational disruption.
- Agile Alignment: Participate in Agile ceremonies (standups, sprint planning, backlog refinement) to balance operational support with planned enhancement delivery.
- Copilot & AI Adoption: Support the organizational adoption of Microsoft Copilot by partnering with business teams to identify productivity opportunities, share best practices, and deliver user guidance.
- Reporting & Business Intelligence: Develop and maintain dashboards, reporting solutions, and KPI tracking using Microsoft tools to deliver actionable business insights.
- Vendor & Lifecycle Management: Act as the primary liaison for vendor support incidents, escalations, system upgrades, and feature implementations
- Continuous Improvement: Analyze recurring support trends to identify system enhancements, optimize workflows, and drive operational efficiency
- Knowledge Sharing & Enablement: Create clear application documentation, knowledge base articles, and end-user training to support organizational readiness and business continuity
What You Bring
- Experience: 7–10+ years of progressive experience supporting, administering, and optimizing complex enterprise business applications
- Agile & Process Familiarity: Proven ability to manage support backlogs and deliver iterative enhancements within an Agile framework
- Vendor & Stakeholder Relations: Exceptional communication and relationship-building skills with a track record of effectively managing vendor escalations and business partners.
- Problem-Solving Mindset: Strong analytical skills with the ability to translate strategic business needs into practical, reliable technology solutions.
- Microsoft Ecosystem: Hands-on experience with Microsoft Power Platform (Power BI, Power Automate, Power Apps) and Dynamics NAV or Business Central
- Emerging Tech: Familiarity with Microsoft Copilot implementation and feature rollout.
- Industry & Enterprise Applications: Prior experience supporting ERP systems, document management, or restoration/property claims software (such as Xactimate, XactAnalysis, Symbility, or Doc-Link) is considered a strong asset.
Why You’ll Love Working Here
- A workplace that values respect, integrity, generosity, excellence and being customer driven
- Opportunities to grow your career and learn from the best in the industry
- A culture that celebrates teamwork, inclusion, and customer-driven service
Of Note:
- We’re proud to support a flexible hybrid approach which gives everyone the best of both worlds. While there are no minimum or maximum time requirements, each team’s need for in-person connections will be different and there will be times you’ll join your colleagues at the office.
At On Side, everything starts with people. We live our values — respect, integrity, generosity, excellence, and customer focus — in everything we do. Join a team that helps families, businesses, and communities rebuild when it matters most. You’ll contribute to a workplace where people come together to bring order to chaos. Make a real impact, do work that matters, and grow your career with us.
*Your application is always reviewed by real people. We don’t use artificial intelligence to screen, assess, or select applicants for this role.
