Caseware is one of Canada's original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles.We are looking for an IT Manager or Senior IT Manager to lead Caseware’s global IT function from our Toronto headquarters. This is a hands‑on leadership role, not a purely managerial one. You will own the strategy, roadmap, and operational performance of IT globally, while also bringing the technical credibility to get involved in architecture decisions, escalated incidents, and infrastructure challenges when needed.You will lead a team across servicedesk, ITSM, infrastructure, and operations. Your two direct reports, the ITSM and Service Desk Lead and the Infrastructure and Operations Lead, each own a major functional area. Your role will be to set direction, remove blockers, develop the team, and ensure the full IT function operates effectively.Our workplace is modern and hybrid. We are cloud‑first where it makes sense, on premise where it matters, and continuously modernizing. Our stack includes AWS, Azure, VMware, Hyper V, Cisco UCS, HCI platforms, and enterprise systems that support our global employee base.Full‑time position. Existing vacancy.Hybrid role requiring the successful candidate to work 3 days a week in our Toronto office, located at 351 King Street East, Suite 1100, Toronto, ON M5A 2W4.What you will be doing:Lead Caseware’s global IT function across service desk, ITSM, infrastructure, cloud, and operations.Own the IT roadmap, including modernization, service delivery, operational resilience, and global scalabilityManage and develop IT leads and technical teams across multiple functional areasProvide technical leadership across AWS, Azure, VMware, Hyper V, Cisco UCS, HCI, networking, and enterprise systemsOversee escalated incidents, root cause analysis, problem management, and major service disruptionsImprove service desk performance, ticket resolution, ITSM processes, asset management, and employee supportPartner with Security, Engineering, Product, Finance, People, and business leaders to ensure IT supports company growthDrive automation, process improvements, vendor management, cost optimization, and platform consolidationEnsure IT operations align with security, privacy, compliance, and audit requirementsIntroduce practical AI and automation into IT operations to improve efficiency, support quality,



and employee experienceAI and Automation FocusIdentify opportunities to use AI across service desk, ticket routing, knowledge management, infrastructure operations, and reportingEvaluate AI enabled tools that improve response times, reduce manual work, and help IT scale globallyPartner with Security and Compliance to ensure responsible AI use, data protection, and proper governanceSeparate useful AI capabilities from hype, with a focus on measurable business valueWhat you will bring:Experience leading IT, infrastructure, service desk, ITSM, or technology operations teams in a global or multi‑site environment.Strong hands on technical background across hybrid enterprise IT environmentsExperience with AWS, Azure, VMware, Hyper V, Cisco UCS, HCI, networking, and enterprise systemsStrong understanding of ITSM, incident management, change management, problem management, and service deliveryExperience managing technical leads, engineers, infrastructure teams, or service desk teamsAbility to operate at both strategic and hands‑on levelsExperience modernizing infrastructure, improving IT operations, and scaling technology servicesStrong communication, vendor management, stakeholder management, and decision‑making skillsExperience with automation, AI enabled tools, or workflow improvements within IT operationsExperience in SaaS, fintech, software, audit, accounting, or regulated technology environmentsExperience supporting global offices and distributed teamsFamiliarity with ITIL, SOC 2, ISO, COBIT, or related operational frameworksExperience with endpoint management, identity, collaboration tools, and enterprise productivity platformsSalary range:The salary range for this position would be between CAD$140,000 and CAD$160,000, depending on experience level.The successful candidate will also be eligible for a discretionary annual bonus, equity participation, and a comprehensive benefits package including medical, vision, dental, life insurance, disability coverage, company matching retirement savings and employee assistance programs.What's in it for you:Innovation is at our core.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.About Caseware:Caseware's cutting‑edge software products are meticulously designed for accounting firms, corporations, and governments. Our teams are continually collaborating, innovating, and building upon our existing suite of products. With a customer‑focused mindset, we are building technology that is shaping what the future of audits, financial reporting, and financial data analytics will look like.With a recent strategic investment from Hg Capital in 2020, Caseware is now in its next major growth phase as we double down on the people and products that have made Caseware so successful to date.One of Caseware's core values is Many Voices, One Team and with that in mind, we’re dedicated to building teams as diverse as our customers in an equitable and inclusive way. We welcome and encourage candidates of all backgrounds to apply. Should you require accommodations or have any questions at any point during the application or interview process, please e‑mail our People Operations team at [email protected] Usage:The recruitment process may use AI assisted tools but not for candidate screening or assessment. All final hiring decisions are made by humans to ensure fairness, transparency, and oversight.Background Check:Any candidates successful in obtaining an offer for a position will need to successfully complete a background check through Certn.Co which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well. Candidates residing in the Netherlands and Germany are excluded from undergoing background checks via Certn.Co.Security and Fraud:Caseware takes the security of candidates seriously. All legitimate communication from us will come from email addresses ending in @caseware.Com and our open positions are always listed on reputable job boards and on our website https://jobs.Lever.Co/caseware. We will never ask for payment or financial information from you. If you receive an unsolicited job offer, proceed with extreme caution.#J-18808-Ljbffr

📌 Senior It Manager - C$140,000 - C$160,000 A Year (Winnipeg)
🏢 CaseWare
📍 Winnipeg