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Underwriting Specialist - E&O​/MedMal; Remote First

Remote / Online - Candidates ideally in
Toronto, Ontario, C6A, Canada
Listing for: Zensurance
Remote/Work from Home position
Listed on 2026-02-27
Job specializations:
  • Insurance
    Underwriter, Insurance Analyst, Insurance Claims, Insurance Risk / Loss Control
Salary/Wage Range or Industry Benchmark: 100000 - 125000 CAD Yearly CAD 100000.00 125000.00 YEAR
Job Description & How to Apply Below
Position: Underwriting Specialist - E&O/MedMal (Remote First)

About Us

Zensurance is redefining commercial insurance for Canadian businesses. As atere Insur Tech, we make getting the right coverage simple, fast, and accessible through a digital‑first experience. Our platform combines advanced technology with deep industry expertise to deliver tailored insurance solutions that help businesses thrive.

Zensurance has been recognised for rapid growth and industry impact, including Deloitte’s Technology Fast 50 (2023‑2025) and the 2022 Top Insurance Employer award. We value ownership, collaboration, and innovation, and thrive on solving complex challenges and making a real impact in an industry ready for change.

Role Overview

We are looking for an Underwriting Specialist specializing in professional lines and medical malpractice to grow, maintain and optimise our specialty casualty portfolio on the Portfolio Underwriting Team. Reporting to the Director of Underwriting, you will work with our Insurance fielding and Operational Underwriting teams to expand the professional liability and Greeting medical malpractice risk‑binding authority within our internal MGA, grow the book of business and maintain a satisfactory loss ratio.

This is a remote‑first role within Canada.

Responsibilities
  • Create and implement profitable professional lines insurance products, including digital and referral underwriting guidelines, pricing strategies, and policy wordings.
  • Maintain and optimise the book of business through data analysis, claims history, and scheduled audits.
  • Be accountable for reaching growth and profitability targets for the professional liability and medical malpractice portfolio.
  • Manage oversight and support of the operational underwriting team, reviewing issuance of policy documents, adjudication of individual accounts and assisting in day‑to‑day underwriting activities as needed.
  • Serve as a subject‑matter expert within Zensurance for professional lines and medical malpractice underwriting.
  • Drive alignment within the insurance department, working closely with the Analytics team to implement changes to the Broker and Operational Underwriting Team.
  • Proactively identify cause and effect relationships and explore alternative solutions to support sound decision‑making.
  • Mentor and coach other underwriters to expand their knowledge base.
  • Collaborate with the Analytics Team & Underwriting Team on gathering data to make underwriting decisions and managing insurance partner relationships.
  • When needed, directly underwrite individual referrals from brokers for complex professional risks.
  • Facilitate training sessions with the Underwriting and Broking teams to communicate appetite and policy changes.
  • Participate in quarterly planning with the Insurance Team to highlight new opportunities and project prioritisation.
  • Correspond with claims adjusters and insurance markets to discuss large loss reserves, settlement strategies, and technical coverage interpretations.
Requirements
  • 5+ years of technical professional lines underwriting experience (E&O, D&O, or medical malpractice).
  • 2+ years of experience working with portfolio optimisation within specialty casualty lines.
  • Experience working with an MGA, or a program‑specific team, or as an internal underwriter at a brokerage is an asset.
  • CAIB, CIP, FCIP, or CRM is an asset.
  • Excellent knowledge of professional liability policy wordings, claims‑made triggers and Canadian provincial regulations.
  • Ability to use data‑driven processes to make decisions.
  • Ability to take the lead on projects involving collaboration with multiple stakeholders.
  • Utilise strategic thinking to execute on ambitious goals.'
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