Windsor On Insurance broker Jobs – 21 Openings This Week

Insurance Broker (Sales)
Billyard Insurance Group Inc —Ontario
- $50,000–$120,000 a year
- Full-time
- Remote
- Sales
- Finance
- High school diploma or GED
- Work from home
- Flexible schedule
Quick apply
Licensed Insurance Broker (Sales)
BILLYARD INSURANCE GROUP-MAPLE —Ontario
- $50,000–$120,000 a year
- Full-time
- Remote
- Sales
- Finance
- High school diploma or GED
- Work from home
Quick apply
Ontario Remote Insurance Broker (Home & Auto) - Commission Only
Billyard Insurance Group - Orangeville —Ontario
- $35,000–$60,000 a year
- Full-time
- Remote
- Sales
- Customer service
- Organizational skills
- Paid time off
- Work from home
Quick apply
Insurance Broker
Billyard Insurance Group Walkerville —Windsor, ON
- Up to $150,000 a year
- Full-time
- Hybrid work
- Sales
- Customer service
- Bachelor's
- Work from home
- Flexible schedule
Quick apply
Life Insurance Broker
Billyard Insurance Group - BIG Ouellette Corners —Windsor, ON
- $45,000–$90,000 a year
- Full-time
- Bilingual
- Sales
- Customer service
- Commuter benefits
- Work from home
Quick apply
4d
Insurance Broker (Sales)
Billyard Insurance Group Vaughan —Ontario
- $35,500.00–$118,797.92 a year
- Full-time
- Remote
- Sales
- Finance
- High school diploma or GED
Quick apply
10d
Bilingual Insurance Consultant
Impact Recruitment —Ontario
- $70,000–$100,000 a year
- Remote
- Bilingual
- English
- Contracts
- Dental care
- Paid time off
Quick apply
2d
Remote - Mortgage Agent - Level I or II required
Guiding Star Mortgage Group —Ontario
- $1.00–$177,822.53 a year
- Full-time
- Remote
- Work from home
- Flexible schedule
Quick apply
Life Insurance Broker
Billyard Insurance Group Walkerville —Windsor, ON
- Up to $150,000 a year
- Full-time
- Sales
- Customer service
- Bachelor's
- Work from home
- Flexible schedule
Quick apply
Account Associate, Commercial Insurance
Masters Insurance —Windsor, ON
- $50,000–$65,000 a year
- Full-time
- Hybrid work
- Microsoft Word
- Microsoft Excel
- Microsoft Outlook
- Dental care
Quick apply
Service Broker
HUB International —Windsor, ON
- From $45,000 a year
- Full-time
- Bilingual
- CRM software
- Customer service
- Dental care
- Employee assistance program
Team Leader, Insurance Operations
HUB International —Windsor, ON
- $62,500–$70,000 a year
- Full-time
- Computer skills
- In-person
- No travel
- Dental care
- Paid time off
7d
Licensed Service Broker
HUB International —Windsor, ON
- $55,000–$62,000 a year
- Full-time
- Hybrid work
- Bilingual
- CRM software
- Sales
- Dental care
- Paid time off
Personal Insurance Sales Advisor
HUB International —Windsor, ON
- $45,000–$50,000 a year
- Full-time
- Sales
- Customer service
- Travel
- Disability insurance
- Tuition reimbursement
Commercial Underwriter- Windsor, ON
All-Risks Insurance Brokers Limited —Windsor, ON
- Microsoft Word
- Microsoft Excel
- Microsoft Outlook
Life Insurance Broker - Licensed
Trinity Solutions Team —Canada
- $35,500.00–$115,035.33 a year
- Part-time
- Remote
- Sales
- Customer service
- Retail sales
- Work from home
- Flexible schedule
Quick apply
6d
Underwriting Performance Manager
Groupe d'assurance South Western —Canada
- $110,000–$130,000 a year
- Remote
- Bilingual
- Management
- English
- Wellness program
- Disability insurance
Quick apply
Financial Planning and Analysis Manager
Groupe d'assurance South Western —Canada
- $110,000–$130,000 a year
- Contract
- Remote
- Bilingual
- Microsoft Excel
- ERP systems
- Wellness program
- Disability insurance
Quick apply

Discover related jobs

Based on your search for insurance broker jobs.

Customs Analyst
Thompson Ahern International —Windsor, ON
A typing test will be sent for verification. The customs analyst is responsible for verifying and processing customs documentation for immediate release.
Quick apply
Virtual Registered Dietitian - Long Term Care
S&R Nursing Homes Ltd. —Windsor, ON
Participate in home-specific continuous quality improvement initiatives, as needed. Minimum 2 years relevant experience in a long term care home is an asset.

Show more related jobs

Explore jobs in cities nearby

Check out jobs in cities near your current location, Columbus

Personal Lines TSR
ICD Insurance Brokers Ltd. —Newmarket, ON
Occasional reception duties which would include, maintain main switchboard and transfer calls accordingly, sort, scan and distribute mail and receive and send…
$40,000–$50,000 a year
Quick apply
Home/Auto/Commercial Insurance Broker
Brokerteam Insurance Richmond Green Branch —Richmond Hill, ON
Property & Casualty license (preferred/must be able to obtain). RIBO license Level 1 or up (required). Managing partner branch program opened for the excellent…
$36,864.67–$77,153.52 a year
Quick apply

Show more jobs in cities nearby

I want to receive the latest job alerts for insurance broker in windsor on

By signing in to your account, you agree to SimplyHired's Terms of Service and consent to our Cookie and Privacy Policy.

Explore jobs in more locations

insurance broker jobs near windsor on

Insurance Broker (Sales)

Billyard Insurance Group Inc -
Ontario

Quick apply

Job details

Permanent | Full-time
$50,000–$120,000 a year

Qualifications

Sales
RIBO License
Finance
High school diploma or GED
Bachelor's
Insurance sales
Business
Communication skills

Full job description

Billyard Insurance Group (BIG) is a leader in the insurance industry, dedicated to building a culture that reflects our core values. At BIG, we Think BIG by exceeding expectations and creating lasting value for our clients, industry, and communities. We Act with Integrity by upholding honesty, transparency, and respect in everything we do. Our clients are at the center of our decisions as we embrace a Client First, Always mindset. We believe in the power of teamwork to Achieve More Together, combining strengths to deliver meaningful solutions. Finally, we Innovate with Purpose by leading the digital insurance revolution, consistently driving quality, enhancing client service, and empowering brokers.

With over 80 locations across Canada and recognition as one of Canada’s Top Growing Companies, BIG is shaping the future of insurance. Join us as we continue to redefine the industry with innovation, collaboration, and excellence.

As a Sales Broker, you’ll represent a recognized industry disruptor and Digital Innovation Award winner, backed by a powerful brand, advanced AI-driven tools, and a dedicated service team that works for you. You’ll have the freedom to build your book of business, the backing of a national brokerage, and the confidence of knowing you’re supported by best-in-class training, market access, and leadership. If you’re an ambitious, relationship-driven insurance professional who thrives in a modern, flexible, and high-performance environment - this is your opportunity to take your career to the next level.

What does the Sales Broker do?

As a Sales Broker, you’ll be the trusted advisor clients rely on to protect what matters most while driving your own business growth in a supportive, high-performance environment. You’ll combine your sales expertise, industry knowledge, and relationship-building skills to deliver exceptional client experiences every day.Here’s what that looks like:

Grow your business: Proactively generate new leads through digital outreach, referrals, networking, and community engagement.
Understand client needs: Conduct in-depth assessments for individuals and businesses, recommending tailored insurance solutions that fit their risks, goals, and budget.
Deliver competitive quotes: Use comparative rating tools and insurer portals to present smart, accurate options for both personal and commercial lines.
Negotiate with confidence: Work with underwriters and insurers to secure the best balance of coverage and pricing for your clients.
Close with precision: Finalize new business and ensure all documentation and client details are accurately captured in the Broker Management System (BMS).
Be the trusted advisor: Guide clients throughout their policy term, respond to changes in coverage needs, and ensure renewals are seamless.
Leverage your support team: Collaborate with our dedicated Corporate Account Management and service teams to deliver a best-in-class client experience.
Maximize every opportunity: Identify cross-sell and upsell opportunities to strengthen client relationships and improve retention.
Stay sharp and compliant: Maintain a strong understanding of insurer products, underwriting guidelines, compliance protocols, and RIBO standards.
Operate ethically and efficiently: Submit complete, accurate applications to reduce turnaround time and minimize E&O exposure.
Keep learning: Participate in ongoing training and CE programs to build your expertise across both personal and commercial lines.
Contribute to team success: Share best practices, collaborate with colleagues, and embody BIG’s core values every day.

Does this sound like you?

You’re a confident, client-focused professional who builds trust through expertise, clear communication, and results. You’ll fit right in if you:

Always put the client first - creating personalized, ethical, and value-driven solutions that make a real difference.
Communicate complex insurance concepts clearly and with empathy, helping clients feel confident in their decisions.
Bring confidence, persistence, and a results-oriented mindset to achieving sales targets and growing your book.
Build lasting relationships based on trust, transparency, and doing the right thing, even under pressure.
Know your insurance products inside and out and can articulate the value to diverse clients.
Use Broker Management Systems comfortably for quoting, policy administration, and client file management.
Deliver accurate, competitive quotes using comparative rating tools and strong market insight.
Keep records organized and data accurate to support compliance, reporting, and client satisfaction.
Understand and apply compliance and licensing standards to uphold regulatory and E&O requirements.
Manage your sales pipeline efficiently including prioritizing tasks, tracking performance metrics, and staying focused on growth.
Solve client and carrier challenges quickly and creatively to keep service seamless.
Connect easily with clients through phone, video, and digital platforms.
Adapt quickly to changing client needs and insurance market conditions.
Enjoy collaborating and sharing success in a team-driven, supportive sales environment.
Thrive working independently, maintaining high standards without daily oversight.
Represent the brokerage with confidence, professionalism, and genuine care in every interaction.

Qualifications:

High school diploma or equivalent
Minimum 2 years of experience in insurance sales or a high-performing sales environment
Must hold an active RIBO license (Registered Insurance Brokers of Ontario) in good standing

Preferred:

Bachelor’s degree in business, finance, or related field an asset
CAIB or CIP designation an asset
Demonstrated success in a commission-based or self-directed sales role an asset
Experience using Broker Management Systems an asset

What We Offer:

Join an award-winning organization recognized for innovation, growth, and industry leadership. We empower you to thrive with the tools, technology, and support to take your career to the next level.

Lucrative Compensation: Enjoy competitive new business commissions, renewal commissions, and ownership in your book of business - because your success should be your reward.*
Leading-Edge Technology: Our proprietary software combines AI-driven underwriting, analytics, and lead management to make doing business in the broker channel smarter, faster, and more profitable.
Recognized Industry Leader: Proud winner of the IBC Digital Innovation Award and Broker of the Year, we’re known as a true disruptor with a bold brand and strong online presence.
Unmatched Sales & Service Support: From digital leads and sales workflows to a dedicated service team managing your book, we’ve built the systems that help you focus on growth.
Broad Market Access: Leverage our strong carrier relationships to offer more choice, value, and confidence to your clients.
Continuous Learning: Through BIG U and access to dedicated internal underwriters, we invest in your expertise every step of the way.
Strong, Inspiring Leadership: Backed by an award-winning CEO and an active, industry-experienced board, you’ll be guided by proven success.
People-First Culture: We put our people at the center of everything we do - fostering collaboration, innovation, and genuine support.
Flexibility That Fits You: Work remotely from anywhere in Ontario or join us in our modern Welland office - the choice is yours.

*This position is compensated exclusively through uncapped commissions earned from the generation of new insurance business. Compensation is entirely performance-based, with no guaranteed salary or minimum earnings. Commissions are payable on new policies written and, where applicable, on policy renewals, in accordance with the company’s commission schedule. Subject to applicable agreements and regulatory requirements, individuals may become eligible over time to retain an ongoing interest in the book of business they personally generate.

Our Commitment to Diversity, Inclusion and Belonging:

Billyard Insurance Group is committed to building a transparent environment where everyone feels heard, welcomed, and included. We believe Diversity, Inclusion, and Belonging are fundamental in our vision to be the leading insurance platform in Canada. BIG is a proud, equal-opportunity workplace that is committed to equal employment opportunity regardless of race, colour, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, or gender identity.

Our Commitment to Accessibility:

Billyard Insurance Group is committed to developing an inclusive, barrier-free recruitment process and work environment. Should you require any accommodation, please inform us, and we will work with you to meet your accessibility needs. For any accessibility-related assistance, requests for information in accessible alternative formats, or to report any accessibility problems, please contact us at [email protected] or 905.346.2190 ext. 10112.

BIG does not currently use AI to screen and/or assess candidates.

This posting is to fill a new open role within our organization.

Pay: $50,000.00-$120,000.00 per year

Benefits:

Company events
Flexible schedule
Work from home

Experience:

Insurance sales: 2 years (preferred)

Licence/Certification:

RIBO or OTL License (required)

Work Location: Remote

Quick apply

Refine Your Search

insurance broker jobs in windsor on

Insurance Broker (Sales)

Licensed Insurance Broker (Sales)

Ontario Remote Insurance Broker (Home & Auto) - Commission Only

Insurance Broker

Life Insurance Broker

Insurance Broker (Sales)

Bilingual Insurance Consultant

Remote - Mortgage Agent - Level I or II required

Life Insurance Broker

Account Associate, Commercial Insurance

Service Broker

Team Leader, Insurance Operations

Licensed Service Broker

Personal Insurance Sales Advisor

Commercial Underwriter- Windsor, ON

Life Insurance Broker - Licensed

Underwriting Performance Manager

Financial Planning and Analysis Manager

Discover related jobs

Explore jobs in cities nearby

I want to receive the latest job alerts for insurance broker in windsor on

Explore jobs in more locations

Job seeker tools

Employer Tools

Browse

Stay Connected