Commercial Insurance Retention Associate… at Zensurance · Toronto

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.

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!