Director of Finance & Operations

  • Cover
  • Toronto, Ontario
  • Apr 04, 2022
Full time Finance

Job Description

Think insurance is boring? We did too. So we built a company that takes everything you think you know about buying insurance and turns it on its head. 
At Cover, we want to become the largest and most customer centric insurance company in the world. 
Founded in 2016, Cover is a mobile-first insurance platform licensed in all 50 states, working with over 35 carriers and underwriting our own insurance products. We were part of Y Combinator’s W16 batch, and have gone on to raise $37 million across three funding rounds backed by world class investors. 
We’re growing fast. In the past year we’ve scaled the team across our San Francisco and Toronto offices. Across our diverse and multi-skilled team we’re working together to deliver a service that’s effortless to interact with, transparently priced, and built on a sustainable and long term footing.
We’re pushing hard to make our vision of insurance a reality and we want dedicated, inquisitive and collaborative people who are ready to play their part in achieving our goal.

We're looking for a Director of Finance to lead and build out the Finance & Operations function at Cover. This role offers the opportunity to own responsibilities across both financial planning & analysis and financial operations. Ultimately, you will be a trusted advisor to senior management on all things finance related as Cover accelerates on its growth trajectory.



  • Build and maintain the financial operating model
  • Lead the end to end budgeting and forecasting cycle
  • Provide recommendations and actionable insights to support decision making around key strategic initiatives
  • Track ongoing performance of KPIs, and compare forecast & actual results
  • Analyze profitability and performance of all product lines
  • Lead month-end, quarter-end, and year-end reporting and reconciliation
  • Prepare financial reporting for board meetings, external investors, and fund raising efforts
  • Oversee all billing, payroll, accounts receivable, accounts payable
  • Build and scale the corporate finance function by implementing and overseeing robust financial controls and best practices



  • 5+ years of relevant experience in investment banking, private equity, management consulting, or strategic finance experience at high-growth technology companies
  • Bachelor degree in Accounting, Finance, Business, Economics, or a related field
  • Completion (or on track to completion) of a CPA, CA, CMA, or CFA designation
  • Best in class financial modeling skills
  • Structured approach to problem solving
  • A self-starter with the ability to prioritize multiple competing projects
  • Ability to work cross functionality with multiple business units


Nice to Have:

  • Basic understanding of the insurance industry
  • Knowledge of SQL and experience with business intelligence tools (e.g. Tableau, Periscope, Looker)
  • Worked at or founded a startup
  • Technically savvy and up to date on the latest technology trends and developments
We Believe in Equal Opportunity
We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, colour, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.