Underwriting Specialist - E&O/MedMal (Remote First)
Zensurance
Toronto, ON, Canada
Posted on Jan 10, 2026
About Us:
Zensurance is redefining commercial insurance for Canadian businesses.
As a leading InsurTech, 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 recognized for its rapid growth and industry impact:
At Zensurance, we value ownership, collaboration, and innovation. Our team thrives on solving complex challenges, challenging the status quo, and making a real impact in an industry ready for change.
If you're looking to build something meaningful in a fast-growing, customer-focused company, we’d love to hear from you!
Our Underwriting Team is critical to providing insurance solutions to small businesses across Canada. We are looking for an Underwriting Specialist specializing in professional lines and medical malpractice to grow, maintain and optimize our specialty casualty portfolio on our Portfolio Underwriting Team.
Reporting to the Director of Underwriting, you will be responsible for working with our Insurance Analytics Team and Operational Underwriting team to expand our professional liability and medical malpractice risk binding authority within our internal MGA, grow our book of business and maintain a satisfactory loss ratio on our book.
This position requires you to take ownership and provide subject matter expertise on professional liability and medical malpractice guidelines, and will allow you the opportunity to grow a book of business with one of Canada’s most exciting Insurtechs.
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 optimize the book of business through data analyses, 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. This includes reviewing the issuance of policy documents, adjudication of individual accounts and assisting in day-to-day underwriting activities as needed.
- Be a subject matter expert within Zensurance for professional lines and medical malpractice underwriting.
- Drive alignment within the insurance department, working closely with the Insurance 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 Insurance Analytics Team & Underwriting Team on gathering data to make underwriting decisions and managing insurance partner relationships.
- As needed, directly underwrite individual referrals from brokers for complex professional risks.
- Facilitate training sessions with the Underwriting and Broking teams to communicate appetite & policy changes.
- Participate in quarterly planning with the Insurance Team to highlight new opportunities and project prioritization.
- 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 optimization 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/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.
- Utilize strategic thinking to execute on ambitious goals.
Benefits & Perks at Zensurance:
At Zensurance, we know that when our people thrive, so does our business. That’s why we offer a flexible, people-first work environment designed to support your well-being, growth, and success.
💻 Work Your Way
• Remote-first setup for added flexibility
• Home office allowance to create a comfortable workspace
• Top-tier tech: "Office in a box" with all necessary tech equipment
• Half days before public holidays: Enjoy half days before long weekends
❤️ Your Health, Your Way
• Flexible health and dental plans for families, including mental health support
• Health & personal spending accounts to invest in wellness your way
• Parental leave top-up, because family comes first
🚀 Investing in Your Growth
• Education assistance reimbursement for courses, conferences, books, and memberships
• Opportunities to learn from industry experts and grow your career
🤝 Staying Connected
• Weekly Friday huddles to share updates and connect across teams
• Virtual & in-person team-building events to strengthen our culture
We’re building something special. Come be a part of it!
Who We Are:
Business is hard work, but insurance doesn’t have to be!
We empower business owners with simple, tech-driven insurance solutions through our online platform.
Our success is fueled by our team-oriented culture and four core values:
DELIVER – We set ambitious goals and achieve them.
INCLUDE – We foster an open and safe space for all.
INTEGRITY – We do what’s right.
INVENT – We create straightforward, innovative solutions.
AI Tools and Your Interview:
We know AI is a valuable tool, and you're welcome to use it to prepare for your interview. However, please don't use AI assistants during the live interview itself. We want to have an authentic conversation with you, and using AI during the interview could affect our evaluation of your suitability for the role.
Just so you know, we use an AI scribe to help us take notes and review interviews, ensuring a fair and clear process.
Diversity & Inclusion:
Zensurance celebrates diversity and is committed to creating an inclusive environment. We welcome applications from all backgrounds and provide accommodations throughout the hiring process. If you need support, let us know, we’re here to help.
Thank You!
We review every application with care to find the best fit for our team.
While we may take a little time to get back to you due to the high volume of applications we receive, know that a real human (not a bot!) is reviewing yours. We appreciate your patience and can't wait to learn more about you!
