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Remote Insurance Jobs in Ontario (NOW HIRING)

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Remote Insurance information

See Ontario salary details

$20K

$69.5K

$141K

How much do remote insurance jobs pay per year?

As of Aug 6, 2026, the average yearly pay for remote insurance in Ontario is $69,468.00, according to ZipRecruiter salary data. Most workers in this role earn between $41,500.00 and $87,500.00 per year, depending on experience, location, and employer.

What are common challenges in a remote insurance and how can they be addressed?

Remote insurance professionals often face challenges such as maintaining consistent client communication across time zones, staying up to date with rapidly changing regulations, and ensuring the privacy and security of sensitive client data. To address these, it is important to establish clear routines, leverage secure digital tools, and proactively communicate availability with both team members and clients. Staying connected with your team through virtual meetings and ongoing training can also help you remain informed and engaged. With the right tools and a proactive approach, these challenges can be successfully managed for a rewarding remote insurance career.

What is a remote insurance?

A Remote Insurance job involves working in the insurance industry from a remote location, typically from home. Roles can vary and may include sales, claims processing, underwriting, customer service, or adjusting. Professionals use digital tools to assess policies, handle client inquiries, process claims, and manage risk assessments. These jobs require strong communication skills, knowledge of insurance policies, and the ability to work independently. Many insurance companies offer remote positions to improve flexibility and reach a broader talent pool.

What skills and qualifications are needed for a remote insurance?

To excel in a Remote Insurance role, you need a solid understanding of insurance products, policy management, and compliance regulations, often supported by previous insurance experience or relevant certification (such as a state insurance license). Familiarity with CRM software, digital document management systems, and secure communication platforms is essential. Strong organizational skills, self-motivation, and the ability to communicate clearly and empathetically with clients set top performers apart. These skills are important to ensure effective client support, regulatory compliance, and productivity in a fully remote environment.

What are the most commonly searched types of Insurance jobs in Ontario? The most popular types of Insurance jobs in Ontario are:
What are popular job titles related to Remote Insurance jobs in Ontario? For Remote Insurance jobs in Ontario, the most frequently searched job titles are:
What job categories do people searching Remote Insurance jobs in Ontario look for? The top searched job categories for Remote Insurance jobs in Ontario are:
Remote Insurance jobs near you
Infographic showing various Remote Insurance job openings in Ontario as of August 2026, with employment types broken down into 85% Full Time, and 15% Part Time. Highlights an 100% Remote job distribution, with an average salary of $69,468 per year, or $33.4 per hour.

Commercial Insurance Retention Associate (Remote First)

Zensurance

Toronto, ON • Remote

CA$52K - CA$58K/yr

Full-time

Re-posted 5 days ago

Job description

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:
 
Deloitte's Technology Fast 50 (2023, 2024, 2025)
Deloitte's Technology Fast 500 (2024, 2025)
Top Insurance Employers (2022)
 
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 Retention team is the frontline for keeping client accounts in good standing. You'll work closely with our customers and external financing partners to resolve billing hurdles and ensure every account stays on track.

Reporting to the Team Lead, you'll play a huge part in our service cycle, making sure "behind-the-scenes" operations turn into a seamless experience for our clients.

Responsibilities:
  • Drive Financial Health: Manage billing queries and proactively connect with clients to collect payments and resolve discrepancies.
  • Broker Partnership: Assist our broker teams with mission-critical tasks, including processing cancellations, reinstatements, and general billing support.
  • Proactive Communication: Triage incoming emails and voicemails, ensuring licensed brokers can focus on complex needs while you handle the operational flow.
  • Accuracy & Compliance: Carefully review new billing contract data and audit files to ensure they meet our strict internal guidelines and process standards.
  • Operational Innovation: Recommend process improvements to streamline how we work with financing companies and improve the overall customer journey.
  • Tech-Driven Support: Monitor Slack alerts, schedule automated client messaging, and jump into clean-up projects to keep our data accurate and reliable.
Requirements:
  • Licensing: You hold a valid RIBO license.
  • Operational Foundation: 1+ year of experience handling administrative tasks, data entry, or high-volume operational workflows.
  • Client-First Mindset: A strong orientation toward both internal and external service-you enjoy helping colleagues and clients alike.
  • Communication Skills: Excellent phone and interpersonal skills, with the ability to translate technical billing issues into clear solutions.
  • Detail & Deadline Driven: Sharp attention to detail with the ability to multitask in a fast-paced, dynamic environment without losing accuracy.
  • Collaborative Spirit: A team player who takes initiative, learns quickly, and thrives in a collaborative, tech-forward set-up.
  • Digital Literacy: Comfortable using Google Workspace, Slack, Zoom, and modern CRM/office software.
$52,000 - $58,000 a year

At Zensurance, we hire for talent and potential.

Our On-Target Earnings (OTE) Structure

Your total cash compensation consists of a guaranteed base salary and a performance-based bonus. Our bonus structure is paid out quarterly and includes multipliers for any performance over target. This means your actual take-home pay can significantly exceed the standard OTE.

Total Potential Earnings

$58,000 OTE (Up to $68,000+ for top performers)

Determining Your Level

Your specific placement within this band will depend on your unique blend of skills, licensing, commercial insurance experience, and your interview performance.

Curious to learn more about our compensation structure? We'll dive into the exact breakdown during your initial interview!

Join Our Sales Team - Empowering Businesses, Building Careers
 
At Zensurance, we believe sales is about building relationships, providing value, and growing together. Here's what makes our team special:
 
We Fuel Your Growth
We invest in your learning with a broad training schedule in your first three months. We have an open feedback culture and provide constant goal setting to help you advance your career.
 
A Culture of Support & Innovation
You'll have the software and technology to manage client interactions, including our in-house Broker Management System (BMS). We give you the tools you need to succeed.
 
Delivering Value to Canadian Businesses
You'll empower Canadian small businesses with a simple approach to insurance. We work with over 50 providers, using our technology to quickly compare quotes. You'll provide expert advice, ensuring clients get the best coverage and price, with in-house claims support.
 
Leaders Who Support Your Success
Our sales leaders mentor and guide you, offering regular one-on-one meetings and daily team support.
 
Clear Career Growth
Our well-defined growth tracks show you what's needed to take your career to the next level, aligning with your skills and ambitions.
 
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.
 
If you're looking for a team that values learning, collaboration, and impactful work, we'd love to meet you!
 
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!
We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.
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