VP Sales - Commercial Insurance
Ai Insurance Organization Inc.
Date: 2 days ago
City: Oakville, ON
Contract type: Full time

Ai Insurance Organization
Ai Insurance Organization is an award-winning insurance brokerage located in Mississauga, Ontario. Our purpose is to meet the evolving needs of all our stakeholders (clients, teammates, insurance partners, suppliers, communities, and society as a whole) and create superior value by disrupting and creating new market segments for both industry and consumer.
Job Purpose
The Vice President of Sales will lead Ai Insurance Organization’s sales division, directly responsible for achieving aggressive growth targets in GWP. The role requires developing and leading high-performing sales teams, expanding client relationships, and effectively managing sales activities focused on Builders Risk, Commercial Lines, Surety Bonds, and Errors & Omissions.
Qualifications / Experience
We thank you as an insurance professional for your submission. We will be in contact with those advancing in this specific recruitment process.
Benefits: Dental care
Location: Hybrid
Disability insurance
Employee assistance program
Pay: Lucrative salary, plus commission
Extended health care
Life insurance
Paid time off
Tuition reimbursement
Ai Insurance Organization is an award-winning insurance brokerage located in Mississauga, Ontario. Our purpose is to meet the evolving needs of all our stakeholders (clients, teammates, insurance partners, suppliers, communities, and society as a whole) and create superior value by disrupting and creating new market segments for both industry and consumer.
Job Purpose
The Vice President of Sales will lead Ai Insurance Organization’s sales division, directly responsible for achieving aggressive growth targets in GWP. The role requires developing and leading high-performing sales teams, expanding client relationships, and effectively managing sales activities focused on Builders Risk, Commercial Lines, Surety Bonds, and Errors & Omissions.
Qualifications / Experience
- 7+ years senior-level sales leadership experience in insurance, specifically commercial insurance sectors.
- Strong background in selling Builders Risk, Commercial Insurance, Surety Bonds, and Errors & Omissions products.
- Demonstrated success in building and leading high-achieving sales teams.
- Proficiency with sales management, CRM software (HubSpot preferred), and data-driven performance tracking.
- Excellent communication, negotiation, and strategic relationship-building skills.
- Proven ability to foster a collaborative, competitive, and performance-driven sales culture.
- Solutions-driven mindset.
- Strong analytical abilities.
- Demonstrated ability to work autonomously and collaboratively.
- Effective relationship management.
- Prioritization skills and high responsiveness.
- Positive and adaptable demeanor.
- Attuned listening skills.
- Proficient in MS Office applications.
- Experience with Broker Management Systems (BMS).
- Knowledge of Company Portals and Document Management Systems.
- Strong verbal and written communication.
- Ability to draft and refine contracts and policy documents.
- Strategically lead sales initiatives to achieve significant year-over-year growth in GWP.
- Recruit, train, and develop a high-performing producer team aligned with Ai Insurance’s market expansion goals.
- Leverage Ai Insurance's CRM and sales enablement platforms (HubSpot, Vertafore SIG) to drive sales performance.
- Develop and implement incentive and referral programs to maximize sales team productivity.
- Foster relationships with strategic industry influencers, brokers, and key clients to enhance Ai Insurance’s market position.
- Regularly evaluate sales strategies and adjust plans based on market conditions, producer performance, and business targets.
- Stay abreast of underwriting philosophies and market trends.
- Convey updates regarding insurance coverages, policies, and regulatory changes.
- Assess and determine the risk associated with commercial insurance proposals.
- Ensure all submissions are accurate, up-to-date, and utilize the latest software. Aim for top-tier submission outcomes.
- Pursue continuous professional development, including CAIB/CIP and related courses.
- Remain updated with industry trends.
- Collaborate effectively across teams and departments.
- Regularly update management and pertinent parties about work progress.
- Aid in skill development of team members and other staff.
- Actively contribute to, and support, all business activities.
- High-pressure, dynamic environment with frequent interruptions.
- Tasks require a combination of accuracy and speed due to complexity.
- Core working hours with potential evening/weekend commitments for events or client obligations.
We thank you as an insurance professional for your submission. We will be in contact with those advancing in this specific recruitment process.
Benefits: Dental care
Location: Hybrid
Disability insurance
Employee assistance program
Pay: Lucrative salary, plus commission
Extended health care
Life insurance
Paid time off
Tuition reimbursement
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