Senior Product Manager (Web and Mobile) – Toronto Cover

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, 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. We were part of Y Combinator’s W16 batch, and have gone on to raise $27 million across three funding rounds backed by world class investors. 

We’re growing fast. In the past year we’ve scaled the team from 30 to 100 people 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.

Role summary:

We are looking for an entrepreneurial product manager to join our consumer product team to develop a seamless and delightful insurance buying experience. By cooperating with engineers, designers, business stakeholders, the product manager will be responsible for finding user problems, defining new opportunities and shipping products that drive our business forward.

  • 5+ years of product management experience building consumer-facing digital products
  • Experience working on products that have deep operational dependencies
  • Ability to lead and influence teams towards a measured outcome you clearly describe
  • Must have a great understanding and empathy for insurance customers; must be a strong customer advocate
  • Rigorous - asks hard questions, validates assumptions, connects the dots
  • Passion for great design, you should know what works, what doesn't and why
  • Entrepreneurial drive and demonstrated ability to achieve stretch goals in an innovative and fast-paced environment
  • Outcome-oriented. Not reactionary but proactive, articulates the desired outcome and works collaboratively to create a path to achieve it


  • Lead the ideation, research, design, development and launch of user-centric products
  • Understand user needs and gather product requirements
  • Goal setting, spec writing, technical requirements, managing project execution, A/B testing, defining product roll-out strategy
  • Manage execution of the product roadmap and build consensus on prioritization which drives product development
  • Define and analyze metrics that inform product success & health

You will play a critical role in our go-to-market success, and beyond.

In your first 3 months on the job, you will:

  • Implement best in class product development and management practices
  • Build alignment across product teams, cross-functional partners (Sales, Marketing, Operations) and Leadership/Executive team
  • Manage sprint boards/ projects with Jira; assess, take charge of, and tune our Agile Scrum process until it sings


  • Preferably CompSci background
  • Strong technical aptitude and attention to detail; can confidently project manage a complex effort with many moving pieces
  • Ability to quickly absorb technical concepts and communicate them to a non-technical audience.
  • Excellent interpersonal skills; people want to hang out with you once they’ve met you, and your team members proactively seek your input and guidance
  • Outstanding presentation, verbal, and written communication skills
  • Some additional, uncorrelated bit of “edge” that makes you stand out from an already exceptional field of talented candidates.
  • Residence in or willingness to move to Toronto
  • Multiple successful product launches under your belt
  • Has gotten hands dirty shipping features across various platforms (iOS, Android, and Web)
  • Must have purchased property insurance previously

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, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.