Team Lead, Underwriting (Remote First)

Zensurance; Remote; CAD 80,000 - 110,000; Full time

Job summary

A leading InsurTech company in Toronto seeks a Team Lead for Underwriting to guide a growing team and enhance operational efficiency. The role involves managing daily operations, fostering collaboration, and ensuring high performance within the team. Ideal candidates will have over 6 years of underwriting experience and 2 years of team management experience, promoting a remote-first work culture with great benefits for their health and professional growth.

Benefits

Remote-first work setup

Home office allowance

Flexible health and dental plans

Education assistance reimbursement

Team-building events

Half days before public holidays

Qualifications

• 6+ years of commercial or specialty insurance underwriting experience.
• 2+ years of experience managing teams.
• Strong proficiency with Google Workspace and Excel or similar office tools.
• Exceptional problem-solving and analytical skills.
• Advanced written and verbal communication skills.

Responsibilities

• Manage team volumes and headcount forecasting.
• Drive improvements to overall team performance.
• Manage relationships with broker teams.
• Supervise and guide a team of underwriters.
• Develop and monitor team goals.

Skills

Commercial insurance underwriting

Team management

Problem-solving skills

Analytical skills

Collaboration skills

Communication skills

Education

University degree in Commerce, Analytics or related field

CIP/CAIB/CRM/FCIP designations

Tools

Google Workspace

Excel

Zendesk

Slack

Salesforce

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!

Team Lead, Underwriting

Reporting to the Director of Insurance, you will play an important role in meeting the organization’s strategic objectives. Your primary responsibilities involve the day-to-day leadership of our fast-growing underwriting team, building and maintaining a culture of high performance and profitable growth by promoting an environment that encourages productivity, collaboration, and a high level of professionalism.

As the first-level people manager, you will provide supervision and coaching to professional-level underwriters and underwriting assistants, support the Director of Insurance and Underwriting Leadership Team in recruitment, continued people development, and performance management. This is a remote-first role within Canada.

Responsibilities – Operational Underwriting

• Manage the team's volumes and headcount forecasting; identify operational and technology areas of opportunity.
• Drive improvements to the overall team performance by refining internal and external processes, and consistently meeting SLAs and KPIs.
• Manage relationships with the broker teams to promote a culture of trust and collaboration.
• Work closely with other stakeholders in the organization, including Brokers, Finance, Insurance Analytics and others to improve end-to-end processes in the organization and to ensure smooth and effective day-to-day interactions.
• Act as a resource to our broker team for any complex underwriting questions.
• Keep up to date with industry trends to deliver excellence in underwriting, and continuously build expertise.
• Maintain data integrity to support the underwriting processes and help the team's objectives.

Responsibilities – Team Management

• Supervise, manage and guide a team of underwriters and underwriting assistants.
• Develop and monitor team goals and performance metrics.
• Identify areas of improvement and growth opportunities for team members, measure their progress toward their objectives over time.
• Promote knowledge sharing and an open, safe work environment.
• Foster and advocate for cross-team collaboration and transparent communication.
• Foster an environment of continuous learning and improvement.

Requirements

• 6+ years of commercial or specialty insurance underwriting experience.
• 2+ years of experience managing teams.
• University degree in a Bachelor of Commerce, Analytics or other type of a business field is preferable.
• CIP/CAIB, CRM, FCIP designations are an asset.
• Strong proficiency with Google Workspace and Excel, or similar office tools.
• Experience using Zendesk, Slack, and Salesforce is an asset.
• A passion for insurance underwriting.
• Exceptional problem-solving and analytical skills.
• Advanced written and verbal communication skills.
• Strong collaboration skills, ability to take the lead in group settings.
• A commitment to continuous improvement, learning and knowledge sharing.

Benefits & Perks at Zensurance

• 💻 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

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!