Head of Underwriting

North America

Full Time

About the Role

BOXX Insurance is a fast-growing Canadian Insurtech company, helping businesses and families stay ahead of cyber risks with Cyberboxx, its break-through product suite. The company is also expanding to USA and further afield.

Due to continued demand for its products and services, BOXX is looking for a Head of Underwriting to join our team. Our ideal candidate will have extensive Cyber underwriting experience in addition to strong market presence, proven leadership and marketing skills. This is an exciting opportunity to work for Canada’s truly global Insurtech company, make a meaningful impact to our success and create a lasting legacy for you.

The Head Underwriting role in insurance companies has traditionally focused on maintaining underwriting standards, driving underwriting quality, and balancing capital utilization across the different lines of business. Where this role is different is that it also includes the opportunity re-define how the industry assesses and prices risk.

This is a timely opportunity for an experienced insurance leader to step up and gain broader exposure and autonomy under the umbrella of the fast-building BOXX brand.

You will work closely with the USA and Canadian operations to accelerate BOXX’s growth and underwriting success. In addition, you will be responsible for managing stake-holder relationships with capacity providers in Lloyd’s of London and domestically and be a subject matter expert for our operations in Europe and other selected markets.



  • Define underwriting strategy and executive plans that will generate continued profitable business growth

  • Lead the Underwriting function for North America

  • Subject market expert for additional selected markets as required

  • Overall responsibility for underwriting performance

  • Establish appropriate internal underwriting procedures and criteria to control risk

  • Oversee the development of the company’s underwriting systems

  • Enhance BOXX’s profile through market presentations, webinars and white-papers

  • Manage the underwriting of Cyberboxx policies within the designated underwriting authority

  • Analyse, evaluate and manage referral files in line with underwriting guidelines and recommendations, coordinating with underwriting staff

  • Meet and negotiate with clients and brokers to build relationships and to develop new and renewal business

  • Review, evaluate and report on loss activity

  • Recruit, train and mentor new team members as the underwriting team expands

  • Contribute to strategic planning, development of complementary products and provide support to new markets

Skills & Qualifications:

  • Preferred cyber, technology and financial lines insurance background (15 years’ total experience)

  • Already operating at a C-suite level or SVP at an insurance company or brokerage

  • Deep understanding across insurance products / strong end-to end product development skills

  • Very strong analytic skills: product strategy, pricing and portfolio management

  • Demonstrated ability to analyze, trouble shoot, and influence stake holders across functions and countries

  • Highly organized and commercially savvy

  • Strong communications (verbal, written, PowerPoint) and relationship management skills

  • Ability to operate in a flat matrix environment

Our Commitment:

BOXX provides opportunities for people who come from all paths. Our team represents a variety of backgrounds, perspectives, and skills. BOXX is a place where everyone has the opportunity succeed. So, however you identify yourself and whatever background you bring, please apply if this is a role that would make you excited to come into work every day.


BOXX embraces a hybrid work environment with a flexible policy that empowers our employees to decide what is best for their own health and wellbeing. We’re committed to continuing this environment into the future.

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About BOXX Insurance

BOXX is a leading Canadian Insurtech and is recognized internationally. In 2021, BOXX was voted as one of the top 25 Insurtech’s in the Americas. In 2020, BOXX was selected for Lloyd’s of London’s highly respected Innovation Lab and selected to participate in the respected Canadian Trade Commission accelerator for top 5 Canadian selected fintechs. The Monetary Authority of Singapore selected BOXX as one of top 20 fintechs from across the world chosen to participate in their 2018 Global Hackathon program.