Senior Manager IT

Caseware Logo

Caseware

πŸ“Remote - Canada

Summary

Join Caseware's global IT team as a Senior Manager and lead a high-performing team, scaling modern infrastructure, and delivering exceptional end-user support. You will manage core platforms like Azure, lead Service Desk operations, and support the hybrid work model. The ideal candidate possesses a strong technical background, thrives in fast-paced environments, and is passionate about people leadership, automation, and service excellence. This role involves managing and mentoring a global team, owning Azure and infrastructure, ensuring Service Desk excellence, managing vendors, collaborating globally, and partnering on security. Caseware offers a collaborative culture, flexible work options, competitive compensation, comprehensive benefits, and opportunities for career growth.

Requirements

  • 5+ years of IT experience, with at least 2+ years in a people management capacity
  • Deep hands-on experience managing Azure, Microsoft 365, Intune, and Service Desk operations
  • Previous experience with virtualization or containerization optimizing resources and applying best practices
  • Proven experience leading distributed or hybrid teams in fast-paced environments
  • Proven experience in leading infrastructure and cloud transformation
  • Strong understanding of endpoint management, asset lifecycle, IT procurement, and office AV/networking
  • Familiarity with ITIL or similar ITSM frameworks and experience improving ticket workflows and KPIs
  • Exceptional interpersonal and communication skills with the ability to influence stakeholders across departments
  • Proven track record of managing vendor relationships including price and feature negotiation
  • Strong project management capabilities and ability to deliver IT initiatives on time and within scope
  • Experience collaborating with global teams and aligning regional operations to global strategy

Responsibilities

  • Manage and mentor a global team of IT professionals across service desk, infrastructure, and support roles
  • Build a high-performance culture through coaching, career pathing, skills assessments, and performance management
  • Champion a service-oriented mindset and hold the team accountable for SLAs, communication, and user satisfaction
  • Lead and maintain Microsoft Azure environments, including identity (Azure AD), virtual infrastructure, and cloud resource management
  • Optimize and manage Office 365, Intune, Defender for Endpoint, Exchange Online, and related M365 services
  • Ensure uptime and performance of critical infrastructure, including office networks, AV systems, VPN, and Wi-Fi solutions
  • Design and execute strategies for endpoint deployment, patching, compliance, and asset lifecycle management
  • Own the delivery, performance, and continuous improvement of the global Service Desk function in the Americas
  • Implement ITSM best practices (e.g., ticket triage, escalation paths, knowledge base, metrics) and define SLAs
  • Leverage ISTM tools (e.g., Jira Service Management, Freshservice) to improve efficiency, transparency, and feedback loops
  • Ensure responsive, empathetic, and technically sound support across remote and onsite users
  • Lead IT procurement and vendor relationships, including contract negotiation, license management, and renewals
  • Standardize hardware/software procurement processes and ensure alignment with budget and compliance goals
  • Manage relationships with MSPs, ISPs, AV integrators, and equipment suppliers to ensure timely and cost-effective delivery
  • Partner with the UK-based EU IT Manager and global counterparts to align on tooling, policies, and standards
  • Support enterprise-wide projects including security initiatives, compliance audits, and office expansion/relocations
  • Provide regular updates and data-driven recommendations to leadership to inform long-term strategy
  • Drive standardization and automation across regions while remaining adaptable to local needs
  • Work closely with the Information Security team to implement technical controls and user training aligned with ISO 27001, SOC 2, and cyber hygiene goals
  • Ensure patch compliance, MFA enforcement, privileged access monitoring, and vulnerability management at the endpoint and infrastructure level
  • Respond to IT-related incidents and participate in root cause analysis, reporting, and remediation plans

Preferred Qualifications

Experience with ISO 27001, SOC 2, or working in regulated or compliance-driven environments

Benefits

  • Innovation is at our core. We work with cutting-edge technology in accounting and financial reporting, constantly pushing the boundaries to create impactful software solutions
  • We are committed to a collaborative culture, where your ideas are valued, and knowledge sharing is encouraged within a supportive, inclusive team
  • Work-life balance is important to us. We offer flexible work options, remote opportunities, and generous time-off policies to ensure a healthy work-life balance
  • We offer competitive compensation, including a competitive salary and comprehensive benefits such as health insurance and retirement plans
  • We are driven by impactful work . Your contributions directly affect how our clients manage financial processes and drive their success
  • Recognition and rewards matter to us . We celebrate hard work through recognition programs, performance bonuses, and opportunities for career growth
  • We embrace global opportunities . Work on international projects and collaborate with a diverse, global team

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