Job Description

Position/Title:

Product + Underwriting Specialist

Type

: Regular/full-time

Work setup:

Remote

Salary:

$58,000 to $80,000 annual

Closing Date:

September 25, 2025

Existing Vacancy

: Yes

Product + Underwriting Specialist

The insurance policies and the underwriting guidelines followed by most providers were designed in the 1970s. Many of these policies and procedures are no longer relevant. So, why are they still offered or used? At Square One, we were wondering about the same thing and decided to do something about it.

We are the only true online home insurance provider in Canada. And we're the only ones in Canada that let clients choose what property they want to insure, so they only pay for what they need. We're committed to making it convenient and easy for clients to do business with us. So, it should be no surprise that we're obsessed with delivering the very best online and offline experiences to our clients.

Your role

As a product and underwriting specialist, you work directly with the company's leadership team to develop new product offerings and underwriting guidelines. Your efforts contribute to the growth and profitability of the company's home insurance portfolio. Your success in this role comes from superior analytical, communication, and research skills. You use your creativity, inquisitiveness, and resourcefulness to identify opportunities and overcome challenges. You are both detail-oriented and organized, handling multiple projects and tasks with ease.

One of the things you value most about working at Square One is the supportive team environment. You're never set up for failure; you receive the coaching, mentoring, training, and tools needed for ongoing success.

Your responsibilities

At Square One, you are directly involved in all product and underwriting initiatives. As such, you have many important responsibilities, including:

Researching new markets, products, and risks. Developing new product offerings and underwriting guidelines. Identifying general rate implications of product or underwriting changes. Ensuring the company complies with legal, licensing, and regulatory requirements. Reviewing and, if appropriate, approving underwriting requests from clients and agents. Keeping apprised of changes in all aspects of the home insurance industry, both locally and internationally. Continuously monitoring catastrophes, such as wind, fire, and flood events, and implementing binding stops to limit new policy sales during these occurrences. Provide monthly industry insurance updates. Cancellation and voiding policies. Updating and maintaining internal underwriting guides and policy documentation. Reviewing client policies as part of the back book clean-up project.

Your qualifications

As a member of the Square One team, you're driven by a desire to contribute to the company's overall success. You achieve this by becoming an expert in your role, taking ownership of your work, and collaborating with a team that values a purpose beyond just making a profit. Those who work with you would describe you as someone who:

Has an excellent understanding of property insurance underwriting principles. Possesses superior analytical, communication, and research skills. Has a natural curiosity and enjoys learning. Uses creativity and resourcefulness to identify opportunities and overcome challenges. Pays close attention to detail and has superior organizational skills. Possesses an exceptional ability to conduct secondary research online. Provide and receive constructive feedback. Is legally entitled to work in Canada at the time of application. Is fluent in English.

Your education + experience

Your experience and education will lay the groundwork for your success at Square One. For this role, you bring:

2 years of property insurance underwriting experience. A high level of proficiency with Microsoft Office applications. Strong knowledge of conducting secondary research using online tools. A degree or diploma in business, commerce, economics, marketing, or equivalent work experience is an asset. A CIP, CAIB, or FCIP designation is preferred. Experience or interest in quality assurance and testing is highly desirable. A general insurance license in your base province preferably in AB, BC, ON, or MB.

Your compensation + benefits

Square One offers a highly competitive package reflected in its comprehensive compensation and benefits plan. This includes:

An annual salary range of $57,312 to $73,244 3 weeks of vacation to start, and an additional week after only 3 years. Flexible medical, dental, vision, and extended health care spending account. Long-term disability coverage. Fully paid Internal and external training. A company profit-share program.

Accessibility

Square One welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process. Learn more about our commitment to accessibility: https://www.squareone.ca/accessibility

Why work for square one?

Probably the shortest and simplest answer for why you should work at Square One is that you want to be part of a tight-knit team where each person's expertise is respected and valued. You're done working at places that tell you what to do, how to do it, and that don't compensate you fairly. To learn more about why you should work for Square One, visit: www.squareone.ca/careers

How to apply

Please submit your resume via Indeed. Your resume must clearly indicate how you meet the qualifications. You have our commitment that we will respond to all applicants and inquiries.

Job Type: Full-time

Pay: $58,000.00-$80,000.00 per year

Benefits:

Company events Dental care Employee assistance program Extended health care Life insurance Profit sharing Work from home
Application question(s):

Please specify all general insurance licenses you currently hold, including the issuing provinces and expiry date. Thanks!
Experience:

home/property insurance underwriting: 2 years (required)
Licence/Certification:

general insurance license in your base province (required) CIP, CAIB, or FCIP designation (preferred)
Work Location: Remote