IT Operations Specialist

Overview of the role

We’re on a mission to modernize insurance, making it simpler, more accessible, and customer-first. The insurance industry is a $1T market that has remained largely untouched by the digital revolution, and PolicyMe is here to change that. As a remote-first, Toronto-based startup with big ambitions, we’re looking for an IT Operations Specialist to help keep our people productive and our systems secure as we scale. While we are remote-first, you must be located in Toronto and willing to work in-office regularly.

In this role, you will own day-to-day IT operations across the company, with a focus on internal support, identity and access management, and SOC 2 controls. You’ll work cross-functionally with Security, People, Engineering, and every business team to ensure employees have the right tools and access, our devices and environments are secure, and incidents are handled quickly and thoughtfully. It’s a high-impact role that blends hands-on technical work, strong security judgment, and exceptional communication.

What you'll be doing:
1. Internal IT support

• Act as the primary contact for IT requests via Jira and Slack.

• Provide hands-on support for macOS and Windows laptops, core tools (Google Workspace, Okta, Slack, Zoom, HubSpot, etc.), VPN and auth issues.

• Troubleshoot and resolve issues quickly, keeping people unblocked.

• Log and document fixes so problems are easier to solve next time.

• Maintain clear Runbooks, checklists, and FAQs (primarily in Notion) so others can follow them when you’re away.

2. Access management, onboarding & offboarding

• Own identity and access management across core systems (e.g., Okta, Google Workspace, TwinGate, CrowdStrike, HubSpot).

• Apply Zero Trust, least privilege, and RBAC to all access decisions.

• Manage laptop and equipment lifecycle and maintain accurate asset inventory.

• Run regular access reviews and audits.

• Coordinate secure device disposal with external partners.

• Lead IT onboarding/offboarding:

• Provision accounts, enroll devices in MDM, configure VPN/EDR.

• Hardware procurement for onboarding and laptop replacements or upgrades.

3. Security, SOC 2 & vendors

• Own SOC 2 Type II IT controls: evidence collection, audits, and working with external auditors.

• Help operate and tune security tooling (MDM, EDR, SSO/MFA, VPN).

• Support incident response and critical issues (including occasional after-hours support).

• Manage key IT/security vendors (hardware, disposal, security, SaaS).

• Ensure device compliance (security tools are installed, policies are deployed)

What we're looking for:
• 3–5+ years in IT support / IT operations, ideally in a SaaS or startup environment.

• Experience with some of our tools: Okta, Google Workspace, TwinGate, CrowdStrike, ManageEngine (or other MDM), Jira, Slack, HubSpot, Zoom, Notion.

• Strong hands-on experience with:

• macOS and Windows support and administration.

• SSO/MFA and access management (Okta or similar).

• MDM and EDR concepts and tools.

• Clear understanding of:

• Zero Trust, least privilege, RBAC.

• IT security in a SaaS-heavy environment.

• Hands-on SOC 2 Type II experience (controls, evidence, working with auditors).

• Excellent communication skills and comfort working with stakeholders at all levels.

• High sense of ownership, responsiveness, and follow-through; comfortable with occasional after-hours incident support.

• Experience working with external vendors.

• Must be located in Toronto and willing to work in-office regularly.

Nice to have:
• Experience automating IT workflows or using AI to improve IT operations.

• Professional certifications (e.g., CompTIA, Microsoft, Security+, etc.).

• Experience in fintech/insurtech or other regulated environments.

• Experience creating and leading OKRs and comfortable presenting to the company

Why join us:
• Generous PTO - 20 vacation days

• A comprehensive benefits plan with premiums paid in full by PolicyMe

• Investment in your professional development, including an L&D budget, AI tooling budget, performance reviews twice a year and ongoing feedback to ensure you reach your highest potential

• An extremely high performing, low-ego, remote-first team that is truly disrupting an old industry

• Option to work from home or our Toronto-based office (bonus: we cover the costs to bring all our employees in-person twice a year for experiential socials!)

• Access to stock options based on performance

• Compensation: The total target cash compensation for this role is $100,000–$125,000 CAD, based on experience. We’ll walk through the details together during the interview.

About PolicyMe:

At PolicyMe, we are Canada’s leading digital insurance solution, offering straightforward and affordable financial protection for families from coast to coast. Our product suite includes Life Insurance, Critical Illness Insurance, and Health & Dental Insurance, all tailored to Canadians' evolving needs. We also offer B2B2C solutions, partnering with organizations to provide seamless digital insurance options. Founded by a team of insurance experts and technology entrepreneurs, PolicyMe is committed to making insurance simpler and more accessible. Since our launch in 2018, we have grown exponentially, selling over $10 billion in insurance coverage to Canadians.

We are proud of the team we’ve built and are excited for those that are yet to join us. We operate with a remote-first culture, attracting top talent from across Canada. If you’re looking for a fast-paced, collaborative environment, working alongside incredibly ambitious yet humble humans, we may be the right place for you! To learn more, visit www.policyme.com.

Additional Notes:

Job Vacancy: This role reflects growth in our team and expanded operational scope. We’re hiring to support increasing demand and continue delivering an exceptional customer experience.

Commitment to Equal Opportunity: PolicyMe is an equal opportunity employer. We welcome applicants of all backgrounds and provide fair consideration regardless of race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability.

Accessibility Statement: We are committed to providing an accessible hiring experience. If you require accommodations during the application process, please indicate this in the “Additional Information” section of your application.

We thank all applicants for their interest, however, only those selected for an interview will be contacted.