IT Systems Administrator (Remote First)

About Us: Zensurance is redefining commercial insurance for Canadian businesses.    As a leading InsurTech, we make getting the right coverage simple, fast, and accessible through a digital-first experience. Our platform combines advanced technology with deep industry expertise to deliver tailored insurance solutions that help businesses thrive.   Zensurance has been recognized for its rapid growth and industry impact:   ✅ Deloitte’s Technology Fast 50 (2023, 2024, 2025) ✅ Deloitte’s Technology Fast 500 (2024, 2025) ✅ Top Insurance Employers (2022)   At Zensurance, we value ownership, collaboration, and innovation. Our team thrives on solving complex challenges, challenging the status quo, and making a real impact in an industry ready for change.    If you're looking to build something meaningful in a fast-growing, customer-focused company, we’d love to hear from you!   We are looking for an IT Systems Administrator to join our growing IT team!  Reporting to the Associate Director, IT, the Systems Administrator’s primary focus is to help deliver project initiatives spanning the configuration, maintenance, and deployment of IT systems, with a strong emphasis on automation, scalability, and security.  This is a hands-on role: you will have the opportunity to take the initiative to solve problems, work through them to full resolution, and aim to fix the underlying issues.  A working knowledge of APIs and automation tooling is central to the role, as much of the work involves eliminating manual processes and building scalable, repeatable solutions. Just as important is the ability to partner with the business: understanding what teams are actually trying to accomplish and translating those asks into practical technical solutions. This is a remote-first role within Canada. Responsibilities:

Administer IT software and services, including but not limited to JumpCloud, Google Workspace (Enterprise), Slack, Zoom, and Confluence/Jira.

Configure and maintain identity and access for third-party tools and services, including but not limited to Salesforce, Zendesk, RingCentral, and M365.

Identify and resolve manual processes through automation tools and initiatives, leveraging APIs to build scalable solutions.

Research, plan, communicate, and implement IT initiatives such as new services or tooling migrations.

Support business requests by understanding stakeholder needs and translating them into effective technical solutions.

Provide Tier 2 support to the business and help manage the IT queue as required, analyzing root causes, assessing the impact of issues, owning problems through to resolution, and escalating to senior team members as needed.

Develop both technical and user-friendly policies and procedures.

Perform other duties as assigned.

Requirements:

3+ years of experience working within IT infrastructure or IT support.

University degree or college diploma in a recognized technical, vocational, or academic program, or equivalent work experience.

Experience implementing SSO, VPNs, and various forms of MFA. 

Working knowledge of SSO connectors, including SCIM and JIT provisioning.

Strong working knowledge of APIs and automation, with the ability to design and build solutions.

Hands-on experience with centralized IAM and software management tools, as well as IT support systems such as Jira Service Management.

Hands-on experience with JumpCloud (or Okta), Google Workspace (Enterprise), Office 365, Salesforce.

Experience using data-driven approaches and metrics to define priorities, translating stakeholder expectations into technical requirements, and facilitating implementation and feature delivery across an organization.

Nice to Have: experience with agile workflows and project management methodologies.

Benefits & Perks at Zensurance:

At Zensurance, we know that when our people thrive, so does our business. That’s why we offer a flexible, people-first work environment designed to support your well-being, growth, and success.

💻 Work Your Way

• Remote-first setup for added flexibility 

• Home office allowance to create a comfortable workspace

• Top-tier tech: "Office in a box" with all necessary tech equipment

• Half days before public holidays: Enjoy half days before long weekends

❤️ Your Health, Your Way

• Flexible health and dental plans for families, including mental health support

• Health & personal spending accounts to invest in wellness your way

• Parental leave top-up, because family comes first

🚀 Investing in Your Growth

• Education assistance reimbursement for courses, conferences, books, and memberships

• Opportunities to learn from industry experts and grow your career

🤝 Staying Connected

• Weekly Friday huddles to share updates and connect across teams

• Virtual & in-person team-building events to strengthen our culture

We’re building something special. Come be a part of it!

Who We Are:

Business is hard work, but insurance doesn’t have to be!

We empower business owners with simple, tech-driven insurance solutions through our online platform. 

Our success is fueled by our team-oriented culture and four core values:

DELIVER – We set ambitious goals and achieve them.

INCLUDE – We foster an open and safe space for all.

INTEGRITY – We do what’s right.

INVENT – We create straightforward, innovative solutions.

AI Tools and Your Interview:

We know AI is a valuable tool, and you're welcome to use it to prepare for your interview. However, please don't use AI assistants during the live interview itself. We want to have an authentic conversation with you, and using AI during the interview could affect our evaluation of your suitability for the role.

Just so you know, we use an AI scribe to help us take notes and review interviews, ensuring a fair and clear process.

Diversity & Inclusion:

Zensurance celebrates diversity and is committed to creating an inclusive environment. We welcome applications from all backgrounds and provide accommodations throughout the hiring process. If you need support, let us know, we’re here to help.

Thank You!

We review every application with care to find the best fit for our team.

While we may take a little time to get back to you due to the high volume of applications we receive, know that a real human (not a bot!) is reviewing yours. We appreciate your patience and can't wait to learn more about you!