About Us:
Propel (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 You:
You 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.
Responsibilities
Infrastructure, Cloud, and Network Operations
- Administer, monitor, and improve Azure infrastructure, Entra ID, Azure networking, virtual machines, storage, resource health, access paths, and related cloud services
- Manage and support Windows Server, AD DS, DNS, GPO, DFS, IIS, VMware, backup/recovery dependencies, and other core infrastructure services as assigned
- Coordinate with vendors/MSPs for office network, firewall, switching, Wi-Fi, ISP, Azure, Cloudflare, and infrastructure work while retaining internal ownership of follow-up and closure
- Support Cloudflare WARP, Zero Trust tunnels, access policies, network routing dependencies, and approved remote/private access paths in coordination with Security and system owners
- Monitor system health, capacity, availability, backup posture, and configuration drift; identify issues before they become recurring support problems
Endpoint, Patch, and Device Management
- Own 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 tooling
- Deploy, monitor, and validate operating system patches, application updates, configuration profiles, security baselines, compliance policies, and endpoint remediation scripts
- Support Windows Autopilot, Intune enrollment, Jamf enrollment, device rebuilds, endpoint readiness checks, BitLocker/FileVault, LAPS, ScreenConnect, Cloudflare WARP, KACE, and Defender onboarding
- Investigate device issues affecting employee productivity, including hardware failures, application problems, update/reboot issues, browser and extension issues, and endpoint-policy conflicts
- Maintain accurate runbooks for device onboarding, rebuild, patching, quarantine, remediation, and return-to-service workflows
Security Operations and Incident Support
- Review, triage, and escalate security alerts from Microsoft Defender, Rapid7, KACE, Intune, Entra sign-in logs, Cloudflare, and related systems according to Propel security and compliance processes
- Work with Information Security on suspicious activity, compromised-device investigations, risky sign-ins, malware alerts, phishing-related endpoint activity, and data-loss or DLP-triggered events
- Gather and preserve evidence through approved tooling, including Defender investigation packages, Live Response where authorized, full scan results, logs, timelines, affected-device scope, and remediation evidence
- Support containment actions when approved, including device isolation, session revocation, access blocking, password/MFA recovery actions, device wipe/rebuild, and controlled return-to-service validation
- Document incident actions, approvals, evidence, and recovery steps in Jira or the approved security record without exposing unnecessary sensitive details to requester-facing comments
Microsoft 365, Identity, SSO, and Data Protection
- Administer and support Microsoft 365 services including Exchange Online, Teams, SharePoint, OneDrive, Defender, Intune, Entra ID, enterprise applications, and related user/device policies
- Understand and support SSO concepts including SAML, OIDC, enterprise apps, app assignments, claims, certificates, groups, MFA, Conditional Access, and break-glass/rollback considerations
- Understand Microsoft Purview, DLP, information protection, retention, alerting, and email/data-flow controls sufficiently to troubleshoot issues and coordinate with Security, Legal/Privacy, and business owners
- Support access lifecycle requests where delegated, while ensuring manager, system owner, Security, P&C, Legal/Privacy, CCB, or data-owner approvals are obtained where required
L3 Support, Coaching, and Escalation
- Serve as the L3 escalation resource for complex endpoint, identity, cloud, network, infrastructure, and security-support issues that cannot be resolved by L1/L2
- Coach L1/L2 team members on troubleshooting methods, evidence collection, ticket quality, customer communication, endpoint tooling, and when to escalate
- Help 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 applications
- Create and maintain practical support runbooks, checklists, knowledge articles, and escalation notes so recurring issues become easier for the team to handle
Change Management, Documentation, and Audit Readiness
- Follow Propel change management and CCB processes for production, security, identity, endpoint, infrastructure, and business-impacting changes
- Prepare accurate change summaries, implementation plans, rollback plans, validation steps, and post-change updates for assigned work
- Maintain current documentation for architecture, access paths, configurations, administrative procedures, ownership boundaries, recurring checks, and operational standards
- Participate in internal/external audits, user access reviews, security reviews, evidence gathering, policy remediation, and compliance-related improvement work
- Ensure tickets and change records clearly show approvals, actions taken, validation results, remaining risks, and closure rationale
Requirements
- College diploma or equivalent certification in Information Technology or related field
- 5+ years of progressive IT systems administration experience in a Microsoft enterprise environment
- Hands-on experience administering Azure, Entra ID, Microsoft 365, Exchange Online, SharePoint, OneDrive, Teams, Intune, Defender, and Conditional Access or related identity/security controls
- Strong working knowledge of Windows Server, AD DS, DNS, GPO, DFS, IIS, PowerShell, endpoint troubleshooting, and infrastructure operations
- Experience with endpoint management and patching platforms such as Intune, Defender for Endpoint, KACE, Jamf, and macOS management tooling
- Working knowledge of networking fundamentals, VPN/Zero Trust access, Cloudflare or similar access tooling, firewalls, switching, Wi-Fi, DNS, routing, and vendor/MSP coordination
- Ability to troubleshoot complex user/device issues across hardware, Windows, macOS, Microsoft 365, browser, endpoint security, network, and application layers
- Experience supporting security investigations, vulnerability remediation, endpoint containment/recovery, audit evidence, and compliance-driven technical work
- Strong documentation, ticket hygiene, change-management discipline, and written communication skills
- Experience with Rapid7, Microsoft Purview/DLP, Cloudflare Zero Trust, Azure networking, VMware, Dell hardware/storage/switching, ScreenConnect, and enterprise backup/recovery processes
- Experience supporting SSO integrations, enterprise applications, SCIM/group-based provisioning, and third-party SaaS access models
- Experience with ITIL-aligned support processes, Jira or Freshservice-style ITSM platforms, CCB/change governance, and audit-ready operational documentation
- Scripting or automation experience with PowerShell and exposure to Python, Bash, Graph API, REST APIs, or infrastructure automation tools
- Relevant certifications such as Microsoft Azure Administrator, Microsoft 365 Administrator, Security Administrator, Endpoint Administrator, Network+, Security+, ITIL, Jamf, or equivalent experience
Benefits to Joining Propel
- Growth and opportunity – we pride ourselves on promoting from within
- Incredible company culture
- Competitive salary and health benefits
- Comprehensive vacation package
- Group health and dental benefits
- Group RRSP program
- Support for new parents
- Diverse and inclusive workplace
Salary Range
$70,000 – $110,000
Final 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 Culture
Propel 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 & Inclusion
Propel 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 Disclosure
We 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.