IT Systems Engineer

League

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profile Job Location:

Toronto - Canada

profile Monthly Salary: $ 81000 - 99000
Posted on: 18 hours ago
Vacancies: 1 Vacancy

Job Summary

About League

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 Leagues 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 healthcares most trusted brands including Highmark Health Manulife Medibank and Shoppers Drug Mart.

About the Role

Were 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 platformswhile building smart automated solutions that keep pace with growth.

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


In this role you will:

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.

Collaboration & Communication

  • 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.

CANADA APPLICANTS ONLY: The Canada-specific compensation range below for this full-time position is exclusive of bonus equity and benefits. This range reflects the minimum and maximum target for base salaries for the position across all Canadian locations. The salary range is intentional to account for the performance and career progressions a Leaguer will experience in the role throughout their time at League. Where in the band you may land is determined by job-related skills/experience. Your recruiter can share more about the specific salary range specific to your skills and experience during the hiring process.

Compensation range for Canada applicants only

$81000 - $99000 CAD

Our employees come from different backgrounds and we celebrate those differences. We are looking for the best candidates for our open roles but do not expect applicants to meet every qualification in order to be considered. If you are excited about what you could accomplish at League and believe you can add value to our team we would love to hear from you.

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 .

Our Application Process:
Applying to a role you love can be exhausting and understanding the next steps can feel vague and uncertain. You have done the hard part of submitting your application; lets do ours by sharing potential next steps
  • 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 Leagues 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.
Here are some additional resources to learn more about League:

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 roles 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 youll enjoy 10 or 20 Flexible Remote Days each quarter for focus and deep-work time. We are committed to fostering a meaningful work environment and connections for all Leaguers regardless of location.

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Use of AI Notice
We are committed to ensuring fairness and transparency throughout our hiring process. League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position. Please check out our stance on using AI in recruitment here.
Review our for information on how League is protecting personal data.

Required Experience:

IC

About LeagueFounded 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 partn...
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Key Skills

  • Clerical
  • Abinitio
  • Chiller
  • Application Engineering
  • ELV
  • AV

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Leading organizations choose League’s healthcare CX platform for personalized digital health experiences that drive measurable results. Get in touch.

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