Strive Health

Oct 22, 2026

System Administrator

Canada

Quinte West, Ontario, Canada

PythonAWS

How You’ll Make An Impact

At Strive Health, patients come first. We’re on a mission to transform chronic conditions by identifying risk earlier, coordinating thoughtful care, and supporting people through every stage of their health journey.

Our work reduces emergency visits, improves outcomes, and helps patients live fuller lives. You’ll work alongside passionate Strivers who care deeply about making an impact, show up for one another as One Team, and find ways to elevate the everyday.

If you’re looking for meaningful work where your contributions truly matter, you’ll feel right at home at Strive!

Benefits & Perks

Hybrid-Remote Flexibility – Work from home while fulfilling in-person needs at the office, clinic, or patient home visits.

Comprehensive Benefits – Medical, dental, and vision insurance, employee assistance programs, employer-paid and voluntary life and disability insurance, plus health and flexible spending accounts.

Financial & Retirement Support – Competitive compensation with a performance-based bonus program, 401k with employer match, and financial wellness resources.

Time Off & Leave – Paid holidays, vacation time, sick time, and paid birthgiving, bonding, sabbatical, and living donor leaves.

Wellness & Growth – Family forming services through Maven Maternity at no cost and physical wellness perks, mental health support, and an annual professional development stipend.

To learn more about our offerings, click here.

What You'll Do

As a Systems Administrator, you will play a vital role in supporting the organization's IT systems and ensuring their reliability, security, and efficiency, by utilizing various tools including automation. A strong desire to overcome obstacles and tackle unfamiliar projects is required. This individual will work with other Strive Systems Administrators in a cloud native environment and assist Support Engineers in meeting the needs of end-users. This position offers an excellent opportunity for experienced professionals to leverage their expertise in systems administration while contributing to the strategic management and optimization of enterprise IT infrastructure. This role will report to the Sr. Systems Administrator.

The Day to Day

Works with other departments to develop solutions to Strive's business requirements.

Installs and configures software applications, patches, and updates to ensure optimal performance and security.

Manages Linux OS, Mac OS and Windows devices in an enterprise remote environment.

Provide technical support and assistance to end-users, including helpdesk support and training.

Develop and maintain technical documentation, including system configuration and troubleshooting guides.

Partner with Strive's security team to find better and more secure ways to implement devices or processes.

Collaborate with other members of the IT team to ensure that systems are integrated and work seamlessly together.

Keep up to date with emerging trends and technologies in systems administration and recommend new solutions and approaches to improve the company's IT infrastructure.

Scripting and automation creation using PowerShell and/or Python.

Administrate and support a variety of systems/platforms including: AWS Cloud, Entra ID, Microsoft 365, SharePoint, MS Intune, Azure Automation, Defender, Iru (Formerly Kandji), Linux and Windows Server.

Manage Iru (Formerly Kandji) and Intune policies, device configurations and software deployments.

Manage Entra ID and Enterprise Apps configuration and maintenance, including Single Sign-On and user provisioning.

Use Automox, Iru, Intune, and other tools to perform system upgrades and patches as needed.

Meet in person with internal and/or external stakeholders to facilitate team and business priorities/opportunities. Business travel may be required for opportunities to connect with stakeholders, serve patients, and attend Strive-sponsored team events.

Minimum Qualifications

High school diploma or GED equivalent.

6+ years combined of related education, experience, and certification.

2+ years of System Administration in enterprise environments.

2+ years of scripting and/or automation development.

2+ years of experience with Cloud computing and infrastructure management (AWS preferred).

2+ years of experience automating tasks via at least one scripting language (Python/Powershell).

2+ years of experience managing Microsoft Entra (Azure Active Directory).

2+ years of experience managing Iru (Formerly Kandji).

2+ years of experience managing Microsoft InTune.

2+ years of experience managing SaaS environments.

2+ years of experience operating in a formalized change management program.

2+ years of experience managing Automox and deploying patches across environment.

1+ years of experience operating in a Scrum or Agile environment.

1+ years CI/CD(GitLab) deployment methodologies.

Internet Connectivity - Min Speeds: 3.8Mbps/3.0Mbps (up/down): Latency <60 ms.

Efficient and reliable transportation, including an active driver's license, allowing for travel across an assigned region to meet business needs.

Ability to travel and be on-site to meet business needs.

Preferred Qualifications

Bachelor's degree in computer science, Information Technology or related field.

Understanding of compliance standards/certifications like HIPAA, SOC, HITRUST, or NIST.

Ability to manage systems in a remote environment.

Strong analytical and problem-solving skills.

Effectively communicate technical knowledge and outcomes with Strive business leaders.

Ability to work independently and as part of a team.

Possess a growth mindset and willingness to implement feedback.

Annual Salary Range: $85,500 - $104,000. This position is also eligible for a target annual bonus of 10%

Final compensation will be determined based on location, experience, and qualifications.

Strive Health is an equal opportunity employer and drug free workplace. At this time Strive Health is unable to provide work visa sponsorship. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, or any other characteristic protected by law. Please apply even if you feel you do not meet all qualifications. If you require reasonable accommodation in completing this application, interviewing, completing any pre-employment testing, or otherwise participating in the employee selection process, please direct your inquiries to talentacquisition@strivehealth.com. We do not accept unsolicited resumes from outside recruiters/placement agencies. Strive Health will not pay fees associated with resumes presented through unsolicited means.

Languages

System Administrator

How You’ll Make An Impact

Benefits & Perks

What You'll Do

The Day to Day

Minimum Qualifications

Preferred Qualifications

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