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Head of Portfolio Underwriting (Remote First)



Toronto, ON, Canada
Posted on Saturday, March 9, 2024
Zensurance is a scale-up InsurTech company that is re-imagining the commercial insurance market. At Zensurance, we want to empower small businesses across Canada to thrive by offering an honest, simplified, and modern approach to insurance. Our main recipe is a combination of modern technology and insurance industry expertise powered by our talented team members.
Being a technology-forward company, we utilize various tools and platforms to create fun, engaging and meaningful work experiences for our employees, as a remote-first company.
We are boldly going where no insurance broker has gone before!
Zensurance is growing our Portfolio Underwriting Team, and looking for a Head of Portfolio Underwriting. This position is paramount in continuing the exciting growth of our internal delegated authority agreements (DUAs) in both premium and profitability.
In this role, you will be owning the overall underwriting strategy for our DUAs as well as providing clear direction to a team of experienced portfolio underwriters with subject matter expertise across GL, Professional Liability and Commercial Property. You will be partnering with the DUA Business Lead to jointly maximize the value proposition and reach our growth and profitability targets.
In this role, you will be collaborating with groups within Zensurance including our Operational UW team to provide UW guidelines, expertise and quality oversight; our internal Brokers to educate and support them with our products; and many other teams. As well as interfacing with external insurance partners from an underwriting perspective to maintain and grow those relationships.
Reporting to the COO, your primary responsibility will be to develop and implement underwriting strategies, shape the future of the portfolio UW team, oversee the quality and risk of our new and active policies, and contribute to the overall profitability of the organization. The Head of Portfolio Underwriting will collaborate with cross functional teams, provide leadership to underwriters, and drive excellence in underwriting practices.
This is a position ideal for those who want ownership and oversight of a growing team in one of the fastest growing insurtechs and companies in Canada.


  • Portfolio Underwriting:
  • Strategic Leadership: define and implement underwriting strategies that align with the organization’s business objectives while providing leadership to the Underwriting Team.
  • Performance: partner with the Business Lead to create a prioritized roadmap of initiatives and work closely with the team to deliver on these initiatives to help drive performance results.
  • Relationships: represent Zensurance with external insurance carriers showcasing underwriting expertise, building trust, and driving to desired strategic outcomes. Leverage your network to help introduce new relationships.
  • Underwriting: develop and update underwriting guidelines, wordings, procedures, and technical pricing.
  • Quality Control: ensure our contracts are well maintained and in compliance, our UW guidelines are internally followed, high quality of human and digital underwriting and policy issuance.
  • Risk Management: oversee the assessment and management of risks associated with the portfolio and ensure regulatory compliance.
  • Portfolio Analysis: conduct regular portfolio reviews to identify trends, opportunities, and potential areas of improvement in collaboration with the data analytics team.
  • Collaboration: collaborate with other departments such as sales, finance, legal, insurance analytics and product to ensure a holistic approach to risk management and portfolio optimization. Work closely with senior leadership to align underwriting strategies with broader business goals.
  • Client Engagement: engage with clients, brokers, and other stakeholders to understand their needs and expectations.
  • Reporting and Analysis: partner with the Business Lead to prepare and present regular reports on portfolio performance, key metrics, and underwriting trends to senior management.
  • Other duties as assigned.
  • People Leadership:
  • Responsible for supervising, managing and guiding a small team of experienced Portfolio Underwriters.
  • Attract, develop, and retain high performing people.
  • Create a high performing team environment by shaping roles & responsibilities, defining roadmap and priorities, designing team processes and dynamics, setting best practices, shaping professional development and career growth paths.
  • Provide mentorship, leadership and/or training to current and new employees.
  • Develop an understanding of company goals and initiatives and help the Underwriters deliver on them.
  • Develop and monitor team goals and performance metrics. Identify areas of improvement and growth opportunities for team members, measure their progress toward their objectives over time.
  • Conduct performance evaluations, provide feedback, and support professional development.
  • Promote knowledge sharing and an open, safe work environment.
  • Foster and advocate for cross team collaboration and transparent communication.
  • Foster an environment of continuous learning and improvement.
  • Perform other duties as assigned.


  • University degree or college diploma in a recognized technical, vocational or academic program or equivalent work experience.
  • 10+ years of commercial insurance experience.
  • 10+ years of commercial portfolio underwriting experience.
  • 5+ years of people management experience.
  • Working within an MGA or in a program-specific division of an Insurance Company or Commercial Brokerage would be an asset.
  • Subject matter expertise in at least one of the following coverages: CGL, Professional Liability, Commercial Property.
  • Knowledge of the Canadian commercial insurance market and players, as well as Lloyds.
  • Ability to use an understanding of market trends, regulatory climate, competitors, and the current challenges faced by the insurance industry to help shape our unique value proposition.
  • Experience in interpreting data, including profit/loss & claims performance, to guide pricing and coverage decisions.
  • Exceptional communication, influencing and organizational skills with staff and customers, as well as with new business partners.
  • Ability to develop strong teams and empower teams and individuals so that they reach their full potential.

Nice to have:

  • CAIB, CIP, CRM, FCIP are an asset.
  • Currently or previously licensed as a commercial broker is an asset.
  • Experience with Google Workspace, Zoom, Slack, or similar office tools.
Perks we offer at Zensurance:
• Opportunity to work for Canada’s fastest-growing #insurtech scale-up
• Primarily remote work environment available to everyone
• Laptop, extra monitor and main accessories are provided
• Extra home office and supplies allowance to help with work-from-home set up
• Comprehensive and flexible health and dental plans to suit all lifestyles, including mental health
• Health/Personal Spending Accounts to subsidize your healthy habits and purchases
• Parental Leave Top Up
• Weekly Friday companywide huddles for casual catch-ups with other departments
• Build next-level relationships with your peers through scheduled companywide virtual and in-person team-building events
• Be a part of something special. We are confident you won’t find any other insurance company like us :)
Who we are. What we're building.
Business is hard work, insurance doesn’t have to be!
At Zensurance we believe that teamwork makes the dream work.
We are passionate about providing business owners with the best insurance solutions at great rates through an online and easy-to-use platform.
Our secret sauce is all about our culture. Here at Zensurance our culture is built on four core values that we live and breathe daily. They are:
INTEGRITY: We do what's right.
INCLUDE: We are an open and safe space for all.
INVENT: We take an innovative approach to creating straightforward solutions for our customers.
DELIVER: We set ambitious goals and hold ourselves accountable for achieving them.
Zensurance celebrates diversity in its workforce structure and encourages applications from all backgrounds.
Zensurance is an inclusive employer that celebrates diversity in its workforce structure. We encourage applications from all qualified candidates and will accommodate applicants’ needs under the respective provincial human rights codes throughout all stages of the recruitment and selection process. Please advise the recruiter if you require accommodation; to ensure your accessibility needs are accommodated throughout this process. Information received relating to accommodation will be addressed confidentially.
We understand that looking for a new exciting opportunity can be time-consuming. We truly appreciate your time in going through the job posting and applying for a position with us.