About UsPropel (TSX: PRL) is the fintech company building a new world of financial opportunity by facilitating access to credit for consumers underserved by traditional financial institutions. Through its AI-driven platform, Propel evaluates customers in a more comprehensive way than traditional credit scores can. Our revolutionary fintech platform has already helped consumers access over one million loans and lines of credit and over one billion dollars in credit.To build a new world of opportunity we bring together the brightest talent to help us build opportunities. We are entrepreneurs and believe in measuring success through results and growing within; talent and hard work never goes unnoticed. At Propel, we are here to change the way employees, customers and shareholders succeed together. We are a team of passionate entrepreneurs, who foster curiosity and growth in our employees. Our culture is why we have been so successful and why our employees choose Propel to build their careers. It is also why we are one of North America’s fastest growing companies and a Best Place to Work. Join us as we change the way employees, customers and shareholders succeed together.About YouYou thrive in a vibrant, entrepreneurial organization where your ideas are valued. You are motivated by goals, a self-starter, and enjoy wearing multiple hats in a fast-growing fintech environment.The Senior IT System Administrator is a senior technical owner within Propel IT, responsible for maintaining reliable, secure, documented, and healthy infrastructure, cloud services, endpoint platforms, identity services, and security-support processes. This hands‑on role requires strong troubleshooting, disciplined change management, and clear communication with IT, Information Security, P&C, business stakeholders, and vendors. As an L3 escalation point, this person owns assigned systems and issues end to end, drives resolution, communicates proactively, and coaches junior team members through standards and practical troubleshooting guidance.ResponsibilitiesInfrastructure, Cloud, and Network OperationsAdminister, monitor, and improve Azure infrastructure, Entra ID, Azure networking, virtual machines, storage, resource health, access paths, and related cloud servicesManage and support Windows Server, AD DS, DNS, GPO, DFS, IIS, VMware, backup/recovery dependencies, and other core infrastructure services as assignedCoordinate with vendors/MSPs for office network, firewall, switching, Wi‑Fi, ISP, Azure, Cloudflare, and infrastructure work while retaining internal ownership of follow‑up and closureSupport Cloudflare WARP, Zero Trust tunnels, access policies, network routing dependencies, and approved remote/private access paths in coordination with Security and system ownersMonitor system health, capacity, availability, backup posture, and configuration drift; identify issues before they become recurring support problemsEndpoint, Patch, and Device ManagementOwn day-to-day administration and health of endpoint management platforms such as Microsoft Intune, Microsoft Defender for Endpoint, KACE, Jamf, and any future macOS MDM replacement such as IRU/Kandji‑style toolingDeploy, monitor, and validate operating system patches, application updates, configuration profiles, security baselines, compliance policies, and endpoint remediation scriptsSupport Windows Autopilot, Intune enrollment, Jamf enrollment, device rebuilds, endpoint readiness checks, BitLocker/FileVault, LAPS, ScreenConnect, Cloudflare WARP, KACE, and Defender onboardingInvestigate device issues affecting employee productivity, including hardware failures, application problems, update/reboot issues, browser and extension issues, and endpoint‑policy conflictsMaintain accurate runbooks for device onboarding, rebuild, patching, quarantine, remediation,



and return‑to‑service workflowsSecurity Operations and Incident SupportReview, triage, and elevate security alerts from Microsoft Defender, Rapid7, KACE, Intune, Entra sign-in logs, Cloudflare, and related systems according to Propel security and compliance processesWork with Information Security on suspicious activity, compromised-device investigations, risky sign‑ins, malware alerts, phishing‑related endpoint activity, and data‑loss or DLP‑triggered eventsGather and preserve evidence through approved tooling, including Defender investigation packages, Live Response where authorized, full scan results, logs, timelines, affected‑device scope, and remediation evidenceSupport containment actions when approved, including device isolation, session revocation, access blocking, password/MFA recovery actions, device wipe/rebuild, and controlled return‑to‑service validationDocument incident actions, approvals, evidence, and recovery steps in Jira or the approved security record without exposing unnecessary sensitive details to requester‑facing commentsMicrosoft 365, Identity, SSO, and Data ProtectionAdminister and support Microsoft 365 services including Exchange Online, Teams, SharePoint, OneDrive, Defender, Intune, Entra ID, enterprise applications, and related user/device policiesUnderstand and support SSO concepts including SAML, OIDC, enterprise apps, app assignments, claims, certificates, groups, MFA, Conditional Access, and break‑glass/rollback considerationsUnderstand Microsoft Purview, DLP, information protection, retention, alerting, and email/data‑flow controls sufficiently to troubleshoot issues and coordinate with Security, Legal/Privacy, and business ownersSupport access lifecycle requests where delegated, while ensuring manager, system owner, Security, P&C, Legal/Privacy, CCB, or data‑owner approvals are obtained where requiredL3 Support, Coaching, and EscalationServe as the L3 escalation resource for complex endpoint, identity, cloud, network, infrastructure, and security‑support issues that cannot be resolved by L1/L2Coach L1/L2 team members on troubleshooting methods, evidence collection, ticket quality, customer communication, endpoint tooling, and when to elevateHelp resolve employee hardware and software issues when advanced technical support is needed, including situations involving policy conflicts, device compliance, account/session issues, or business‑critical applicationsCreate and maintain practical support runbooks, checklists, knowledge articles, and escalation notes so recurring issues become easier for the team to handleChange Management, Documentation, and Audit ReadinessFollow Propel change management and CCB processes for production, security, identity, endpoint, infrastructure, and business‑impacting changesPrepare accurate change summaries, implementation plans, rollback plans, validation steps, and post‑change updates for assigned workMaintain current documentation for architecture, access paths, configurations, administrative procedures, ownership boundaries, recurring checks, and operational standardsParticipate in internal/external audits, user access reviews, security reviews, evidence gathering, policy remediation, and compliance‑related improvement workEnsure tickets and change records clearly show approvals, actions taken, validation results, remaining risks,



and closure rationaleRequirementsCollege diploma or equivalent certification in Information Technology or related field5+ years of progressive IT systems administration experience in a Microsoft enterprise environmentHands‑on experience administering Azure, Entra ID, Microsoft 365, Exchange Online, SharePoint, OneDrive, Teams, Intune, Defender, and Conditional Access or related identity/security controlsStrong working knowledge of Windows Server, AD DS, DNS, GPO, DFS, IIS, PowerShell, endpoint troubleshooting, and infrastructure operationsExperience with endpoint management and patching platforms such as Intune, Defender for Endpoint, KACE, Jamf, and macOS management toolingWorking knowledge of networking fundamentals, VPN/Zero Trust access, Cloudflare or similar access tooling, firewalls, switching, Wi‑Fi, DNS, routing, and vendor/MSP coordinationAbility to troubleshoot complex user/device issues across hardware, Windows, macOS, Microsoft 365, browser, endpoint security, network, and application layersExperience supporting security investigations, vulnerability remediation, endpoint containment/recovery, audit evidence, and compliance-driven technical workStrong documentation, ticket hygiene, change‑management discipline, and written communication skillsExperience with Rapid7, Microsoft Purview/DLP, Cloudflare Zero Trust, Azure networking, VMware, Dell hardware/storage/switching, ScreenConnect, and enterprise backup/recovery processesExperience supporting SSO integrations, enterprise applications, SCIM/group‑based provisioning, and third‑party SaaS access modelsExperience with ITIL-aligned support processes, Jira or Freshservice‑style ITSM platforms, CCB/change governance, and audit‑ready operational documentationScripting or automation experience with PowerShell and exposure to Python, Bash, Graph API, REST APIs, or infrastructure automation toolsRelevant certifications such as Microsoft Azure Administrator, Microsoft 365 Administrator, Security Administrator, Endpoint Administrator, Network+, Security+, ITIL, Jamf, or equivalent experienceBenefits To Joining PropelGrowth and opportunity – we pride ourselves on promoting from withinIncredible company cultureCompetitive salary and health benefitsComprehensive vacation packageGroup health and dental benefitsGroup RRSP programSupport for recent parentsDiverse and inclusive workplaceSalary Range$70,000 – $110,000Final compensation is determined by market conditions, location, and the candidate’s experience, skills, and education. This role may also be eligible for performance‑based incentive programs and total compensation may include variable incentives, such as bonuses and commissions. This posting is for an existing vacancy within our organization.Our CulturePropel brings together the brightest talent to build opportunities. We are entrepreneurs who measure success through results and growth from within; talent and hard work never go unnoticed. Our team fosters curiosity and growth, making Propel one of North America’s fastest‑growing companies and a Best Place to Work.Commitment to Diversity & InclusionPropel welcomes and encourages applications from all groups, including Indigenous peoples, women, visible minorities, persons with disabilities, people from gender and sexually diverse communities, and those with intersectional identities. Should you require accommodation throughout any stage of the recruitment and selection process, please specify your requirements when submitting your application and we will work with you to meet your needs.AI DisclosureWe use AI to assist in reviewing applications and assessing candidates. These tools support our recruitment team, however, all hiring decisions are made by our trained hiring managers and recruitment professionals, not AI.#J-18808-Ljbffr

📌 Expert It System Administrator Wanted - $70,000 - $110,000 A Year (Winnipeg)
🏢 Dynamo Technologies
📍 Winnipeg