Apply on Kit Job: kitjob.ca/job/2e0s21

Title: Legal Counsel, Insurance Products

Type: Regular / Full-time

Location: Alberta, British Columbia, or Ontario

Work Setup: Remote

Hours of Work: 40 hours per week, Monday - Friday

Salary Range: CA$117,000 – CA$140,000 per year

Closing Date: April 17, 2026

Existing Vacancy: Yes

Your Role
You love law but prefer to work for a single client. By gaining an intimate knowledge of the company, you provide accurate, quality, and relevant advice on a wide spectrum of legal matters. You also benefit from a flexible work schedule and a better work-life balance.

The way in which home + auto insurance is distributed, fulfilled, and serviced is changing. More and more people choose to research, buy, and manage their insurance online. So, you want to build your career at a progressive company that excels in the online space.

Square One was the first online home insurance provider in North America. And, we’re the only home insurance provider that lets clients choose what property they insure so they only pay for what they need. In 2023, we began offering online car insurance in Ontario, and in 2024, we expanded our car insurance offering into Quebec.

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 experiences to our clients.

Reporting to the company’s General Counsel, you will serve as a key strategic advisor to our underwriting, product, sales, and claims teams. This role is unique to Square One’s relationship with our business partners, requiring a hands-on approach to drafting policy language, providing coverage advice, and ensuring our operations remain compliant with various laws and regulations. You will bridge the gap between complex legal principles and practical business solutions.

Your success in this role comes from your strong knowledge of legal principles combined with exemplary research and dispute resolution skills. You use active listening skills to clearly understand issues and objectives. You work well under pressure because you are detail-oriented and highly organized. All these skills enable you to come up with smarter and more innovative approaches to solving problems.

One of the things you will enjoy most about Square One is the supportive team setting. You know you’re never set up for failure; instead, you get all the coaching, mentoring, training, and tools you need for continued success.

Your Responsibilities
As a technical specialist, you are the main point of contact for internal team members who have legal questions related to our home and auto insurance products. Your responsibilities include:

Policy wordings & product development





- Draft and/or review of policy wording in collaboration with the product + underwriting team to ensure wordings accurately reflect the intended risk appetite and meet plain language standards.
- Assist in the launch of new insurance products by researching legal trends and competitor wordings to ensure market-leading and legally sound documentation.
- Proactively research and advise on emerging risks in home insurance.
- Ensure policy wordings, endorsements, and internal practices strictly adhere to applicable insurance legislation and regulatory filing requirements.

Coverage committee & legal opinions

- Serve as a member and facilitate the meetings of Square One’s coverage committee, providing legal analysis on complex or high-value coverage issues.
- Research and draft legal opinions regarding policy interpretation, coverage issues, duty to defend, and other related matters.
- Provide legal opinions on the intent of certain policy wordings.
- Support the claims team in liaising with external legal firms when specialized expertise or litigation support is required.

Regulatory & compliance

- Monitor and interpret changes to insurance laws and industry guidelines, including Ontario’s “Fair Treatment of Customers” and “Take All Comers” rules.
- Ensure company products, wordings, policies, practices, and procedures comply with insurance laws and industry guidelines.

Complaints & dispute resolution

- Support the Complaints Officer by reviewing and advising upon complex customer complaints and final position letters.
- Assist in the resolution of disputes before they escalate to litigation, focusing on risk mitigation and brand protection.

Your Qualifications
You have a desire to contribute to the overall success of the company. You do this by directing your own work and collaborating with a team with a broader purpose than just making a profit. You have the following qualifications:

- Deep understanding of insurance legislation and provincial regulatory frameworks across Canada.
- Exceptional drafting skills with an ability to simplify complex legal concepts.
- Strong communication and presentation skills.
- Strong attention to detail and organizational skills.
- Ability to build and maintain strong professional relationships across the company and business partners.




- Ability to communicate complex legal issues and risks in terms that non-legal colleagues can understand.
- Leverages solid judgment and critical thinking skills in a highly autonomous role.
- Fluency in French is a significant asset.

Your Experience + Education
Your experience and education, combined with the training we provide, helps ensure your success at Square One. For this role, you have:

- Education: LL.B. or J.D.
- Bar Admission: Member in good standing with a provincial Law Society (e.g., LSO, Law Society of BC).
- Experience: 3–6 years of post-call experience, ideally with a background in insurance coverage or defence litigation. Experience within an MGA or insurance carrier is highly preferred.

Your Compensation + Benefits

You appreciate that Square One personalizes your compensation and benefits in the same way it personalizes policies for its customers. Your compensation and benefits plan includes:

- A competitive base annual salary.
- 4 weeks of vacation to start and an additional week after only 3 years.
- Flexible medical, dental, vision, and extended health care coverage.
- Short- and long-term disability coverage.
- In-house and external training paid by Square One.

You also participate in Square One's employee profit share and performance bonus programs. Under these programs, when the company achieves its annual targets, you share in its profits.

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.

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, see .

Pay: $117,000.00-$140,000.00 per year

Benefits:

- Casual dress
- Company events
- Employee assistance program
- Extended health care
- Life insurance
- Paid time off
- Profit sharing
- Store discount
- Work from home

Application question(s):

- Bar Admission: Are you currently a member in good standing with a provincial Law Society (e.g., LSO, Law Society of BC)
- What has been your experience in working in the insurance law/insurance carrier field? (Please provide the issue/situation and how you resolved it)

Education:

- Bachelor's Degree (required)

Experience:

- post-call experience in insurance coverage or defense: 3 years (required)

Language:

- French (preferred)

Work Location: Remote

Apply on Kit Job: kitjob.ca/job/2e0s21

📌 Legal Counsel, Insurance Products (Canada)
🏢 Square One Insurance Services
📍 Canada