Senior IT Manager - PolicyMe

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 a Senior IT Manager to lead the IT Support function as we expand into the next chapter!

What You'll Be Doing

You will be a senior member of the team, and a cross-functional leader within PolicyMe. This is an opportunity to completely reshape the IT strategy and execution as PolicyMe moves to the next stage of scale and growth, building durable policies and process that will be used for years to come! You will be the decision-maker! In your day-to-day, this will lead you to:

• Define the vision and roadmap for IT Support: Articulate strategic goals for the IT Support team and define the roadmap. Communicate progress against the roadmap and goals to all key stakeholders (Business Operations, Engineering, Leadership, People and Culture).
• Hands-on ownership of IT equipment: Ensure PolicyMe employees have continuous access to the tools they need (laptops, external monitors, etc.), while ensuring inventory management and disposal follow proper governance. Manage budgets and strategic equipment selection decisions.
• Prioritize workload: Decide what IT Support team members invest time on and in what order. Prioritize process improvements, security rollouts, bugs, and maintenance activities through a disciplined process.
• Collaborate on Information Security: Work closely with senior leaders from Business Operations and Engineering to maintain a robust information security program. Directly own access control and maintenance of PolicyMe’s SOC 2 certification.
• Coordinate on-call availability: Design and execute support availability timelines and SLAs within the company based on defined priority levels.
• Develop the backlog: Ideate with stakeholders across PolicyMe and manage a backlog of new IT initiatives to meet employee needs and improve back-end integrity.
• Rally the team behind secure best practices: Serve as the central point across all functions to remove IT-equipment and access-related roadblocks. Ensure information security and IT governance are well understood across the organization.
• Coordinate launch releases: Work with Engineering and Business Operations to ensure patches and security releases are thoroughly tested and ready for launch.
• Measure and learn: Measure key metrics for the IT support team and report outcomes to the broader organization.

What We Are Looking For

• Relevant IT support experience: 3-5 years of experience in IT support management, Information Security, or Engineering, preferably in a startup or scale-up technology setting, with a track record of delivering measurable results.
• A hands-on aptitude: Ability to plan strategically while remaining a hands-on contributor for day-to-day tasks.
• AI mindset and willingness to innovate: Excited about AI opportunities in IT, actively learning new applications, and ready to guide PolicyMe's AI adoption and AI-first capabilities.
• Exceptional collaboration skills: High emotional intelligence to serve as the connector between diverse organizational stakeholders.
• Technical curiosity: Naturally curious about how systems work and comfortable diving into complex technical topics alongside software engineers.
• Mindset for risk assessment: Risk-mindful approach to problem-solving, understanding the sensitivity of personal information handled by the business, with the ability to assess and communicate risk probability and severity.
• Strong problem-solving skills: Ability to structure ambiguous problems, leading solutions from concept to deployment that solve both immediate issues and future edge cases.
• Strategic decision-making: Ability to balance tradeoffs, rely on data-supported reasoning, and clearly communicate second and third-order impacts.

Why Join Us

• Generous PTO - 20 vacation days
• Comprehensive benefits plan with premiums paid in full by PolicyMe
• Professional development support (L&D budget, AI tooling budget, biannual performance reviews, ongoing feedback)
• High-performing, low-ego, remote-first team environment
• Option to work from home or from our Toronto office (with covered costs for bi-annual in-person team socials)
• Performance-based stock options
• Compensation: Target cash compensation is $132,000–$154,000 CAD, based on experience

About PolicyMe

At PolicyMe, we are Canada’s leading digital insurance solution, offering straightforward and affordable financial protection for families. Our product suite includes Life Insurance, Critical Illness Insurance, and Health & Dental Insurance, alongside B2B2C solutions. Founded in 2018, PolicyMe has grown exponentially, selling over $20 billion in insurance coverage to Canadians.