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 rapid-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 whileretaininginternal ownership of follow-up and closure

Support Cloudflare WARP, Zero Trust tunnels, access policies, network routing dependencies, and approved remote/private accesspaths in coordination with Security and system owners

Monitor system health, capacity, availability, backup posture, and configuration drift;identifyissues 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, andvalidateoperating system patches, application updates, configuration profiles, security baselines, compliance policies, and endpoint remediation scripts

Support Windows Autopilot, Intune enrollment,Jamfenrollment, device rebuilds, endpoint readiness checks, BitLocker/FileVault, LAPS,ScreenConnect, Cloudflare WARP, KACE, and Defender onboarding

Maintainaccuraterunbooks for device onboarding, rebuild, patching, quarantine, remediation, and return-to-service workflows

Security Operations and Incident Support

Review, 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 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 whererequired

L3 Support, Coaching, and Escalation

Serve as the L3 escalation resource for complexendpoint, 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 elevate

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 andmaintainpracticalsupportrunbooks, 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

Prepareaccuratechange 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

Experience supporting security investigations, vulnerability remediation, endpoint containment/recovery, audit evidence, and compliance‑driven technical work

Strong documentation, ticket hygiene,change‑managementdiscipline, 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,JiraorFreshservice‑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

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 ourtrained hiring managers and recruitment professionals, not AI.

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📌 Sr. IT System Administrator (Ontario)
🏢 Propel Holdings
📍 Ontario