VP Sales - Commercial Insurance

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

• 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.
  
  

Behavioral Competencies

• 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.
  
  

Technical 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.
  
  

Key Result Areas/Essential Functions

• 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.
  
  

Risk Oversight

• 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.
  
  

Education/Compliance

• Pursue continuous professional development, including CAIB/CIP and related courses.
• Remain updated with industry trends.
  
  

Teamwork

• 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.
  
  

Working Conditions

• 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 are committed to providing accommodations and achieving a barrier-free workplace for individuals with disabilities. We provide a safe inclusive work environment and welcome all candidates with disabilities, visible minorities and LGBTQ2S+. Should you require an accommodation to participate in our recruitment process, we will support you by considering your individual accessibility needs.

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