Sr. Systems Administrator

Propel Holdings Inc.; Ontario; On-site; CAD 75,000 - 100,000; Full time

Job summary

A leading fintech company in Ontario is looking for a dynamic Windows Systems Administrator. You will play a key role in managing and evolving the core infrastructure, driving process improvements, and ensuring the availability and security of enterprise services. Join a vibrant team within a culture that values growth and innovation.

Benefits

Growth and opportunity within the company

Competitive salary and health benefits

Group health and dental benefits

Support for new parents

Diverse and inclusive workplace

Qualifications

• 5+ years of experience in Windows Systems Administration.
• 5+ years managing Azure environments and cloud services.
• Proficient with PowerShell scripting and automation.

Responsibilities

• Administer and maintain core infrastructure services.
• Implement and enforce platform-level security standards.
• Serve as Level 3 support for escalated incidents.

Skills

Windows Systems Administration

Azure Cloud Management

Microsoft 365

PowerShell Scripting

Technical Communication

Education

College diploma in Information Technology

Tools

Azure

VMware

Microsoft 365

Active Directory

Job description

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’ve been so successful and why our employees choose Propel to build their careers. It’s also why we’re 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:

As a fast-growing fintech, we stay true to our startup roots. You picture yourself within a vibrant and entrepreneurial organization where your ideas will be heard, and you have an opportunity to showcase your talent. You are motivated by goals, a self-starter and like to wear multiple hats.

You are a talented professional looking for a career, not a job. Reporting to the Director, IT & Security Operations, you will thrive in a dynamic environment and be passionate about managing enterprise systems, driving process improvements, and enabling operational excellence. You’ll be a key player in maintaining and evolving our core infrastructure, supporting mission-critical services, and ensuring enterprise-wide availability, performance, and security.

Responsibilities

• Administer and maintain core infrastructure services, including:
• Windows Server (2016+), Active Directory (EntraID, ADDS, DNS, GPO), DFS, IIS
• Azure cloud services and virtualization platforms (Azure, VMware)
• Microsoft 365 services including Exchange Online, Endpoint Manager, SharePoint, and OneDrive
• Enterprise applications and services (ERP, SAN, SFTP, JIRA)
• Endpoint and mobile device management (JAMF, KACE)
• Implement and enforce platform-level security standards in accordance with corporate security policies
• Participate in internal and external IT security compliance audits
• Maintain and regularly review system security configurations and access controls
• Serve as Level 3 support for escalated infrastructure and system-related incidents
• Manage and resolve system issues in accordance with defined SLAs
• Support change management procedures for infrastructure and application updates
• Participate in root cause analysis and proactive trend identification
• Work cross-functionally with IT, security, and business teams to troubleshoot issues and drive performance optimization
• Create and maintain detailed documentation on systems architecture, operational procedures, and configuration standards
• Lead infrastructure-related projects and mentor junior administrators
• Participate in after-hours support rotation and planned maintenance windows (evenings and weekends required)

Requirements

• College diploma or equivalent certification in Information Technology or related field
• 5+ years of experience with Windows Systems Administration
• 5+ years of experience managing Azure environments and cloud services
• 5+ years working with the Microsoft 365 platform (Exchange Online, Defender, SharePoint, OneDrive)
• Proficiency with PowerShell scripting and automation
• Strong knowledge of ADDS, DNS, GPO, DFS, IIS, and Windows Server (2016+)
• Hands-on experience with VMware and Azure virtualization
• Proven ability to work independently and manage infrastructure projects from start to finish
• Strong communication skills with a focus on cross-team collaboration and technical leadership

Nice to have

• Experience with JAMF and KACE endpoint management platforms
• Familiarity with Dell storage solutions and networking tools (e.g., FortiClient, Cloudflare, Dell Switches)
• Exposure to additional scripting languages (e.g., Python, Bash) and automation tools
• Working knowledge of ITIL processes and service management frameworks

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

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 accommodate your needs.

We welcome and encourage applications from individuals from all groups, including aboriginal, women, visible minorities, and persons with disabilities, regardless of race, ethnicity, family status, national origin, age,people from gender and sexually diverse communities, and/or people with intersectional identities.

We thank all applicants for showing an interest in this position. Only those selected for an interview will be contacted. No agencies or phone calls.