IT Systems Engineer

Founded in 2014, League is the leading healthcare consumer experience (CX) platform, powered by artificial intelligence (AI), reaching more than 63 million people around the world and delivering the highest level of personalization in the industry. Payers, providers, and consumer health partners build on League’s platform to deliver high‑engagement healthcare solutions proven to improve health outcomes. League has raised over $285 million in venture capital funding to date, powering the digital experiences for some of healthcare’s most trusted brands, including Highmark Health, Manulife, Medibank, and Shoppers Drug Mart.

About the Role

We’re looking for an

IT Systems Engineer

to help integrate, scale and secure the internal systems that power a fast‑growing organization. This role is hands‑on and impact‑driven, focused on endpoints, identity, and SaaS platforms—while building smart, automated solutions that keep pace with growth.

You’ll operate beyond traditional helpdesk work, owning systems end‑to‑end, improving how tools integrate, and embedding security into everyday IT operations. You’ll also have opportunities to work with modern AI‑powered tools and automation to streamline workflows and improve the employee experience.

Internal IT Operations

Be part of day‑to‑day operation of corporate macOS endpoints (macOS).

Manage device lifecycle at scale : provisioning, configuration, patching, and offboarding.

Provide tier 2 / 3 support for complex endpoint, access, and SaaS issues.

Identity, Access & SaaS

Administer identity and access management systems (SSO, MFA, RBAC).

Own user lifecycle workflows (onboarding, role changes, offboarding) in a fast‑changing environment.

Manage and integrate core SaaS tools across productivity, engineering, and business functions.

Continuously review and improve access controls using least‑privilege principles.

Solutions Engineering, Automation & AI Enablement

Design and implement IT solutions that scale with company growth.

Automate repetitive IT workflows using scripting, APIs, and no‑ / low‑code tooling.

Integrate SaaS platforms using native integrations, webhooks, and APIs.

Evaluate and support AI‑powered IT and productivity tools (e.g., AI assistants, ticket triage, workflow automation) to reduce manual work and improve response times.

Maintain clear documentation, runbooks, and standards to support rapid onboarding and change.

Apply secure configuration and hardening standards across endpoints and SaaS systems.

Support security monitoring and alert triage in partnership with the Security team.

Assist with incident response, investigations, and remediation efforts related to IT systems.

Support compliance and audit readiness through strong access controls and operational hygiene.

Partner closely with Engineering, Security, People, and Business teams.

Communicate clearly during incidents, changes, and rapid growth periods.

Bring an ownership mindset and continuously look for ways to improve how IT operates.

What You Bring

Bachelor of Science degree (BS) in Computer Science (or a related field)

Minimum 4 years of experience in internal IT operations, systems administration, or enterprise IT roles.

Strong analytical and problem‑solving skills.

Strong experience managing endpoints (macOS required; Windows optional).

Hands‑on experience with identity and access management (Okta, Kolide, Google Workspace).

Experience administering and integrating SaaS platforms (1Password, Proofpoint, NetSkope, Okta, Slack, Jira, GitHub, Crowdstrike).

Ability to script or automate workflows using Python, Shell, or similar tools.

Familiarity with APIs, SaaS integrations, or workflow automation tools.

Practical understanding of IT security fundamentals (endpoint security, access control, monitoring).

Comfortable working in fast‑moving, ambiguous environments with shifting priorities.

Clear, pragmatic communicator with a solutions‑first mindset and “Can Do” attitude.

Nice to Have

Experience with MDM tools (e.g., Addigy, AMB).

Experience with EDR, SOAR, or endpoint security platforms.

Exposure to AI‑powered IT or productivity tools.

Familiarity with compliance frameworks (e.g., NIST, HITRUST, GDPR).

Relevant IT or security certifications.

Security & Compliance Responsibilities

Follow company information security policies and secure operating practices.

Support audits, reviews, and compliance activities as required.

Promptly report security incidents, risks, or policy violations.

Compensation Range (Canada applicants only)

$81,000 – $99,000 CAD

We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. If you are an individual in need of assistance at any time during our recruitment process, please contact us at recruitinginfo@league.com.

Our Application Process

You should receive a confirmation email after submitting your application.

A recruiter (not a computer) reviews all applications at League.

If we see alignment with League’s needs, a recruiter will reach out to learn more about your goals. The recruiter will also share the team‑specific interview process depending on the roles you are exploring.

The final step is an offer, which we hope you will accept!

Prior to joining us, we conduct reference and background checks. Additional checks could be required for US Candidates, depending on the role you are exploring.

Work Location

We have a mix of office‑centric roles based in our vibrant Toronto office and remote‑eligible roles based anywhere in Canada or US. Each job posting will indicate where the role will be based. Regardless of the role’s posted location, all Toronto‑area Leaguers (living within 65 km of our downtown HQ) collaborate in‑office Monday through Thursday. Depending on your distance to the office, you’ll enjoy 10 or 20 flexible remote days each quarter for focus and deep‑work time.

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