Chief Underwriter (Oakville)

Job Purpose

The Chief Underwriter will build and 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 insurance 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 construction insurance, including at least 5 years in a senior underwriting leadership role.
• High-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.

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

1. Direct the assessment and underwriting of complex contractor, ensuring prudent risk selection and optimal terms.
2. Lead, mentor, and develop a high‑performing underwriting team, fostering a culture of continuous learning and professional excellence.
3. Collaborate closely with senior management, sales, actuarial, and claims departments to refine underwriting strategies and enhance competitive positioning.
4. Continuously monitor underwriting performance and profitability metrics; proactively recommend adjustments to strategies and practices as necessary.
5. Manage strategic relationships with brokers, agents, reinsurers, and key stakeholders within the surety industry.
6. Stay abreast of industry trends, competitor activities, regulatory changes, and emerging risks; leverage insights to position the company competitively.
7. Establish, communicate, and oversee the implementation of underwriting policies and guidelines aligned with company objectives and regulatory requirements.

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, aiming for top‑tier submission outcomes.

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.

Why Join Approved Casualty and Surety?

• 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 a cutting‑edge and collaborative work environment.
• A culture that values integrity, collaboration, excellence, and innovation.

Benefits

• Dental care
• Disability insurance
• Employee assistance program
• Pay: Lucrative salary, plus commission
• Extended health care
• Life insurance
• Paid time off
• Tuition reimbursement

Location

Hybrid