Chief Underwriter
Ai Insurance Organization Inc.
Date: 2 days ago
City: Oakville, Ontario
Contract type: Full time

Approved Casualty and Surety
Approved Casualty and Surety is a respected MGA leader in providing specialized surety solutions to a wide range of businesses across Canada, with a focus on Commercial and Contract Surety. We are dedicated to innovation, excellence, and delivering unparalleled underwriting services tailored to our clients’ unique needs. As we continue to grow, we are seeking a highly experienced Chief Underwriter to strategically lead and advance our surety underwriting operations.
Job Purpose
The Chief Underwriter will lead the surety underwriting team, shaping strategic underwriting guidelines, maintaining exceptional underwriting standards, and driving profitability and sustainable growth. This senior role demands an experienced underwriting professional with deep knowledge of surety markets, outstanding analytical skills, strategic leadership capabilities, and a proven record of building and mentoring underwriting teams.
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
Approved Casualty and Surety is a respected MGA leader in providing specialized surety solutions to a wide range of businesses across Canada, with a focus on Commercial and Contract Surety. We are dedicated to innovation, excellence, and delivering unparalleled underwriting services tailored to our clients’ unique needs. As we continue to grow, we are seeking a highly experienced Chief Underwriter to strategically lead and advance our surety underwriting operations.
Job Purpose
The Chief Underwriter will lead the surety underwriting team, shaping strategic underwriting guidelines, maintaining exceptional underwriting standards, and driving profitability and sustainable growth. This senior role demands an experienced underwriting professional with deep knowledge of surety markets, outstanding analytical skills, strategic leadership capabilities, and a proven record of building and mentoring underwriting teams.
Qualifications / Experience
- Bachelor’s degree in Business, Finance, Risk Management, or related field. Advanced certifications (CPCU, AFSB, CRM, FCIP) strongly preferred.
- Minimum 10+ years of progressive underwriting experience in surety or related commercial lines, including at least 5 years in a senior underwriting leadership role.
- Expert-level knowledge of surety bond products, underwriting methodologies, risk assessment, and pricing strategies.
- Demonstrated ability to develop, articulate, and execute underwriting strategies that achieve business and financial objectives.
- Strong analytical, problem-solving, and decision-making skills, paired with meticulous attention to detail.
- Exceptional interpersonal, communication, and negotiation skills, with the ability to effectively engage with internal stakeholders and external partners.
- Proficient knowledge of regulatory environments affecting the surety market and compliance best practices.
- 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.
- Direct the assessment and underwriting of complex surety bonds, ensuring prudent risk selection and optimal terms.
- Lead, mentor, and develop a high-performing underwriting team, fostering a culture of continuous learning and professional excellence.
- Collaborate closely with senior management, sales, actuarial, and claims departments to refine underwriting strategies and enhance competitive positioning.
- Continuously monitor underwriting performance and profitability metrics; proactively recommend adjustments to strategies and practices as necessary.
- Manage strategic relationships with brokers, agents, reinsurers, and key stakeholders within the surety industry.
- Stay abreast of industry trends, competitor activities, regulatory changes, and emerging risks; leverage insights to position the company competitively.
- Establish, communicate, and oversee the implementation of underwriting policies and guidelines aligned with company objectives and regulatory requirements.
- 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.
- 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.
- Opportunity to lead and significantly impact a growing, dynamic, and respected organization.
- Competitive compensation package including attractive salary, comprehensive benefits, and performance incentives.
- Professional growth opportunities supported by an innovative and collaborative work environment.
- A culture that values integrity, collaboration, excellence, and innovation.
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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