Senior Product Manager (Web & Mobile) - Toronto at Cover
Toronto, Ontario, CA

Cover is a national insurance brokerage, licensed in all 50 states, working with more than 35 carriers. We source our customers entirely from our iPhone and Android apps. Right now, for searches of insurance on the US AppStore we rank in the top 10 on any given day. The company is backed by Y Combinator and many other world-class investors.

We're reshaping the way that insurance is sold, and building product to make sure our customers get the most out of the insurance policies they buy. We're proud of our customer-centric focus, and the elegant apps we build to better serve our customers. Cover has significant backing by world-class investors and is based in San Francisco and Toronto.

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 are building a modern, fair and sustainable insurance entity

Our vision is to make insurers rates fairer, easier to understand, and delightfully simple to manage, irrespective of what our customers need to protect.

Insurance is a very big business

There are hundreds of admitted insurance companies processing north of $500B in insurance premiums across all lines of property, life and specialty insurance in the US. Most of these companies operate on technology platforms built many decades ago. As a result, they suffer from glaring inefficiencies that are passed on to their customers in the form higher prices, poor customer and product experiences that haven’t adapted to the expectations of modern customers.

We’re trusted insurance advisors every step of the way

We have access to just about every insurance market in the US. Our customers can trust that we’re fulfilling our fiduciary responsibility to them with an exhaustive / programmatic search that gets them the best value for every dollar of premium spent with Cover. We’re there from policy inception, making sure that we save our customers money, and heartache from being inadequately insured, to navigating claims for every line of property business.

Our approach involves overcoming significant operational and technical challenges.

Our approach requires bringing service, analytics and technology together in an elegant way, and doing so in an industry that has historically lacked all three. This will mean applying creativity and flexibility to every interaction with customers and partners, while always looking for ways to make them - and, by extension, us - more successful.


You’re here to work on hard things, learn, grow, support and challenge your peers

Building a national insurance entity from scratch is something few people can claim to have done - you’ll be one of them. We’re passionate about bringing world-class product and consumer experiences to insurance, and financial services, building fair & sustainable products and delivering lasting value to our customers. We’re looking for people who won’t settle for less than building category-defining products.

We currently offer the following benefits and will continually evolve them with the goal of efficiently attracting, retaining, and leveraging the very highest quality talent:

  • Highly competitive salaries and stock option grants
  • Health, dental, for you and your family
  • Flexible work hours
  • Unlimited vacation policy
  • A slew of perks that make your life outside of work easier


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.