Top Benefits
About the role
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)
✅ 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!
The General Counsel & Compliance Officer (GC & CO) will be the principal legal advisor to the executive team, responsible for overseeing all legal affairs and establishing a robust, scalable regulatory compliance framework for the organization. This role requires a candidate who is comfortable with both hands-on contract work and strategic execution. The successful candidate would also be business savvy and be able to contribute to all areas of the organization.
This role will report to the CEO as a member of the Executive Team and have a close partnership with Travelers Indemnity Company, Zensurance's parent company.
Please note: This is a remote-first role, meaning you can primarily work from home, but should expect to join us in the office (Located Downtown Toronto) periodically.
Responsibilities:
-
- Contract Drafting & Review: Lead all commercial legal matters, including sophisticated contract negotiation, drafting, and review (including broker agreements, vendor contracts, and client-facing documents).
- Procurement Support: Provide critical legal oversight and guidance on major corporate procurement initiatives, ensuring vendor relationships comply with internal policies and regulatory requirements.
- Risk Management: Identify, assess, and mitigate legal and regulatory risks across all business operations in alignment with Canadian brokerage, financial and insurance regulations.
- Problem solving: Help Zensurance navigate legal complexities and mitigate evolving legal risks amidst its business ambitions
- Compliance Function: Develop, implement, and manage a scalable and effective compliance management system tailored to the evolving regulatory landscape of the insurance brokerage sector in Ontario and Canada.
- Regulator Communications: Serve as the primary contact and expert liaison for all provincial (e.g., RIBO) and federal regulatory bodies, managing audits, inquiries, and license requirements.
- Policy Development: Establish and enforce internal compliance policies, including anti-money laundering (AML), privacy (PIPEDA, etc.), data security, and consumer protection regulations.
- Training: Develop, facilitate and deliver mandatory compliance training programs to all employees to promote a culture of integrity and compliance.
- Purpose: Drive purpose by setting the overarching strategic direction and vision for the function, balancing short and long-term priorities with Zensurance’s business objectives.
- Leadership: Provide leadership, guidance, mentoring and coaching to the Zensurance employees, fostering a compliance-aware culture, as well as a culture of creativity, appropriate risk taking and experimentation across Zensurance.
- Role modelling: Acts as a role model for high integrity and ethical behaviours.
- Commercial & strategic capabilities: Ability to proactively identify and solve for legal, risk and compliance related issues in consideration of Zensurance's business objectives and vision beyond the immediate agenda.
Requirements:
-
- Contract Drafting & Review: Lead all commercial legal matters, including sophisticated contract negotiation, drafting, and review (including broker agreements, vendor contracts, and client-facing documents).
- Procurement Support: Provide critical legal oversight and guidance on major corporate procurement initiatives, ensuring vendor relationships comply with internal policies and regulatory requirements.
- Risk Management: Identify, assess, and mitigate legal and regulatory risks across all business operations in alignment with Canadian brokerage, financial and insurance regulations.
- Problem solving: Help Zensurance navigate legal complexities and mitigate evolving legal risks amidst its business ambitions
- Compliance Function: Develop, implement, and manage a scalable and effective compliance management system tailored to the evolving regulatory landscape of the insurance brokerage sector in Ontario and Canada.
- Regulator Communications: Serve as the primary contact and expert liaison for all provincial (e.g., RIBO) and federal regulatory bodies, managing audits, inquiries, and license requirements.
- Policy Development: Establish and enforce internal compliance policies, including anti-money laundering (AML), privacy (PIPEDA, etc.), data security, and consumer protection regulations.
- Training: Develop, facilitate and deliver mandatory compliance training programs to all employees to promote a culture of integrity and compliance.
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.
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. 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.
About Zensurance
Zensurance is a Toronto-based technology company and leading source for small business insurance in Canada. We make it easy, quick, and affordable for startups, self-employed professionals, contractors, and small businesses to get insured.
Through our highly regarded client support team and network of over 50 insurance providers, Zensurance provides customers with industry-leading premium savings and the confidence to thrive in today’s market.
#Zensurance #WeAreZensurance
Top Benefits
About the role
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)
✅ 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!
The General Counsel & Compliance Officer (GC & CO) will be the principal legal advisor to the executive team, responsible for overseeing all legal affairs and establishing a robust, scalable regulatory compliance framework for the organization. This role requires a candidate who is comfortable with both hands-on contract work and strategic execution. The successful candidate would also be business savvy and be able to contribute to all areas of the organization.
This role will report to the CEO as a member of the Executive Team and have a close partnership with Travelers Indemnity Company, Zensurance's parent company.
Please note: This is a remote-first role, meaning you can primarily work from home, but should expect to join us in the office (Located Downtown Toronto) periodically.
Responsibilities:
-
- Contract Drafting & Review: Lead all commercial legal matters, including sophisticated contract negotiation, drafting, and review (including broker agreements, vendor contracts, and client-facing documents).
- Procurement Support: Provide critical legal oversight and guidance on major corporate procurement initiatives, ensuring vendor relationships comply with internal policies and regulatory requirements.
- Risk Management: Identify, assess, and mitigate legal and regulatory risks across all business operations in alignment with Canadian brokerage, financial and insurance regulations.
- Problem solving: Help Zensurance navigate legal complexities and mitigate evolving legal risks amidst its business ambitions
- Compliance Function: Develop, implement, and manage a scalable and effective compliance management system tailored to the evolving regulatory landscape of the insurance brokerage sector in Ontario and Canada.
- Regulator Communications: Serve as the primary contact and expert liaison for all provincial (e.g., RIBO) and federal regulatory bodies, managing audits, inquiries, and license requirements.
- Policy Development: Establish and enforce internal compliance policies, including anti-money laundering (AML), privacy (PIPEDA, etc.), data security, and consumer protection regulations.
- Training: Develop, facilitate and deliver mandatory compliance training programs to all employees to promote a culture of integrity and compliance.
- Purpose: Drive purpose by setting the overarching strategic direction and vision for the function, balancing short and long-term priorities with Zensurance’s business objectives.
- Leadership: Provide leadership, guidance, mentoring and coaching to the Zensurance employees, fostering a compliance-aware culture, as well as a culture of creativity, appropriate risk taking and experimentation across Zensurance.
- Role modelling: Acts as a role model for high integrity and ethical behaviours.
- Commercial & strategic capabilities: Ability to proactively identify and solve for legal, risk and compliance related issues in consideration of Zensurance's business objectives and vision beyond the immediate agenda.
Requirements:
-
- Contract Drafting & Review: Lead all commercial legal matters, including sophisticated contract negotiation, drafting, and review (including broker agreements, vendor contracts, and client-facing documents).
- Procurement Support: Provide critical legal oversight and guidance on major corporate procurement initiatives, ensuring vendor relationships comply with internal policies and regulatory requirements.
- Risk Management: Identify, assess, and mitigate legal and regulatory risks across all business operations in alignment with Canadian brokerage, financial and insurance regulations.
- Problem solving: Help Zensurance navigate legal complexities and mitigate evolving legal risks amidst its business ambitions
- Compliance Function: Develop, implement, and manage a scalable and effective compliance management system tailored to the evolving regulatory landscape of the insurance brokerage sector in Ontario and Canada.
- Regulator Communications: Serve as the primary contact and expert liaison for all provincial (e.g., RIBO) and federal regulatory bodies, managing audits, inquiries, and license requirements.
- Policy Development: Establish and enforce internal compliance policies, including anti-money laundering (AML), privacy (PIPEDA, etc.), data security, and consumer protection regulations.
- Training: Develop, facilitate and deliver mandatory compliance training programs to all employees to promote a culture of integrity and compliance.
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.
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. 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.
About Zensurance
Zensurance is a Toronto-based technology company and leading source for small business insurance in Canada. We make it easy, quick, and affordable for startups, self-employed professionals, contractors, and small businesses to get insured.
Through our highly regarded client support team and network of over 50 insurance providers, Zensurance provides customers with industry-leading premium savings and the confidence to thrive in today’s market.
#Zensurance #WeAreZensurance