Senior IT Manager

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: You will articulate the strategic goals for the IT Support team and define the roadmap for how we get there. You will communicate progress against the roadmap and goals to all key stakeholders (e.g. Business Operations, Engineering, Leadership, People and Culture).
• Hands-on ownership of IT equipment: You will take on the direct responsible of ensuring PolicyMe employees have continuous access to the tools they need (laptops, external monitors, etc.), while also ensuring the inventory management and disposal follow proper governance. This will include managing budgets and strategic thinking on equipment selection decisions.
• Prioritize what to work on: You will have to decide what other IT Support team members invest time on and in what order. By developing and executing a disciplined process, you will prioritize process improvements, security rollouts, bugs and maintenance activities.
• Collaborate in PolicyMe’s Information Security Committee: You will work closely with senior leaders from Business Operations and Engineering to maintain a robust information security program where your direct responsibilities will include ownership of access control and maintenance of PolicyMe’s SOC 2 certification. This requires deep attention to detail on role-based access control and third party vendor management.
• Coordinate on-call availability: You will be responsible for designing and executing alongside the IT support team, on support availability timelines and SLAs within the company based on defined priority levels.
• Develop the backlog: You will ideate with stakeholders across PolicyMe and then manage a backlog of new IT initiatives to meet our employee’s needs, improve our back-end integrity, innovate and ultimately reach the defined vision.
• Rally the team behind secure best practices: You will serve as the central point across all functions and ensure that any IT-equipment and access-related roadblocks are removed to achieve success. This includes ensuring information security and IT-related governance is well understood and communicated across the organization.
• Coordinate the launch: You will work with the Engineering and Business Operations teams to ensure that the patches and new security releases has been thoroughly tested and are ready to launch.
• Measure and learn: You will measure the key metrics for our IT support team and report out to the broader organization.

What are we looking for:

• Relevant IT support experience: You have 3-5 years of experience in IT support management, Information Security, or Engineering, preferably in a start-up or scale-up technology setting. You can speak to your track record of leading projects and delivering measurable results.
• A hands-on aptitude: You have the ability to both think and plan strategically while also remaining a “do-er” for the day to day tasks and activities. This hands-on attitude is incredibly important at PolicyMe and flows through our culture even at the most senior levels.
• AI mindset and willingness to innovate: You are excited about the opportunities that AI presents for the IT area and are actively learning about new applications and technologies. You are keen to play a major role in the transition of PolicyMe’s AI adoption and development of AI-first capabilities.
• Exceptional collaboration skills: You have high emotional intelligence and can "be the glue" between many different stakeholders in the organization.
• Curiosity and highly comfortable with technical topics: You are naturally curious about how everything works. You will work closely with some wicked smart Engineers, so you know when to ask clarifying questions and are not shy about diving into complex topics.
• A mindset for risk identification and assessment: You understand that the PolicyMe business model inherently handles high sensitive personal information. You take a risk-mindful approach to problem solving and identify risks before they present themselves as problems. You are comfortable assessing the probability and severity of risks and communicate these clearly.
• Strong problem solving skills: You have the ability to take an ambiguous problem and structure it yourself. You are someone who can start with an idea and manage it from concept to deployment. You present and execute solutions that are durable, that is they will solve today’s problem and tomorrow’s edge case!
• Strategic decision making: You can balance tradeoffs and consider many side to a problem before arriving at a decision. Decisions are based on strong supporting data, consider the second and third order impacts, and are communicated concisely and clearly.

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 $132,000–$154,000 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 $20 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.