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Cover // mobile insurance brokerage platform
Product, Full Time    Toronto, Ontario, Canada    Posted: Tuesday, July 02, 2019
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We are looking for an insurance product leader with a proven ability to develop, & maintain outperforming insurance products
About Cover

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 & Android apps. Right now, we rank #1 for searches of insurance on the AppStore in Canada, & within the top 10 in the US on any given day. The company is backed by Y Combinator & many other world-class investors.

Role summary:

As an Insurance Product Manager, you will come armed with insurance industry knowledge, & requisite knowledge of insurance product development, rate analysis, & navigating a disparate regulatory environment. You will work with leadership across each function of the business to support the development of insurance products that are novel, reflect our values & are underwritten to a profit. You will do this alongside a team of colleagues who have founded & exited successful tech startups, & come from a diverse set of technology companies.

  • You will own all aspects of insurance product development.  You will build a team around you to develop a roadmap for state by state roll out, handle filings & provide rate analysis. This high-performing individual can be based out of our San Francisco or Toronto offices.


  • Youre excited to work in an early-stage, entrepreneurial environment with high-caliber colleagues
  • You are fired up to go beyond - working with select fronting & reinsurance partners to align economic interests, & align with outperformance of your products
  • You want to get your hands dirty by learning (or improving at) what it takes to be an operator
  • You can build relationships & work effectively across functions, to drive the development & implementation of insurance products you design
  • You always have a perspective on what to do next, & can prioritize on the fly as new needs & information emerges
  • You are experienced working with senior executives, & you know how to translate those interactions to tangible impact
  • You can find information where none exists - including interviews, mystery shopping, & other creative methods of developing sources of insight
  • You can absorb & synthesize information rapidly, separating the signal from the noise


  • Selects, trains, & develops an effective high performing team of analysts
  • Conducts performance appraisals, recommends salary adjustments, promotions & transfers.
  • Monitors the quality & productivity of work within the unit, & recommends & implements changes on an on-going basis for improvement.
  • Lead the research, analysis, & recommendations for final rate picks & product coverages.
  • Manages filings & negotiates with Department of Insurance to gain approvals.
  • Provides support on the development of state strategies by focusing analyst resources on value-added research & analysis. This includes comparative rater supplied data, competitive filings, system process, vendor products, & other elements.
  • Keeps abreast of industry trends in the area of sales, losses, legal developments, coverage, packaging & distribution methods.  Makes reports & recommendations as appropriate.
  • Monitors trends in PL business including new business, quote & close rates, growth, profit, retention & customer profiles to identify needed changes.
  • You will play a critical role in our go-to-market success, & beyond.

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

  • Begin to build a team of pricing & business analysts to support the development of product filings
  • Take over key relationships with reinsurance partners, fronting carriers
  • Interface with our policy administration software team to further refine our rating engines
  • Assist in the development of rate filings, spot-check assumptions, start to work with respective DOIs to launch in our next set of states

After that, you will:

  • Manage a team of highly analytical product, audit & compliance analysts of different levels 
  • Lead team that provides competitor analysis, filings, & and performs rate testing
  • Manage projects that drive product development, pricing strategy, profitability & growth 
  • Help chart out a nationwide insurance product roll out strategy
  • From here, you may:
  • Lead all of insurance product development at Cover
  • Move into Business Operations, Product, or Growth, where you may see opportunities to flex / expand a skillset


  • Bachelors degree, preferably with an engineering or business focus
  • Demonstrated knowledge of the Personal Lines Property & Casualty insurance industry including pricing, product, underwriting practices, & competitive analysis
  • Experience working with DOIs, internal & external legal counsel, & the management & execution of insurance filings
  • Strong technical aptitude & attention to detail; can confidently project manage a complex effort with many moving pieces
  • Excellent interpersonal skills; people want to hang out with you once theyve met you, & your team members proactively seek your input & guidance
  • Outstanding presentation, verbal, & written communication skills
  • The ability to not be deterred - relentless in driving to impact
  • 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, the San Francisco Bay area or Toronto

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

Building a national insurance entity from scratch is something few people can claim to have done - youll be one of them. Were passionate about bringing world-class product & consumer experiences to insurance, & financial services, building fair & sustainable products & delivering lasting value to our customers. Were looking for people who wont settle for less than building category-defining products.

We currently offer the following benefits & will continually evolve them with the goal of efficiently attracting, retaining, & leveraging the very highest quality talent:
Highly competitive salaries & stock option grants
Health, dental, for you & 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 & 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.

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