Agency Development Jobs in Chicago, IL (NOW HIRING)

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The Commercial Surety Regional Manager is responsible for the underwriting, marketing, production, profitability, and overall management of a regional Commercial Surety portfolio. This position serves as the senior underwriting leader for the assigned territory and is accountable for achieving premium growth, underwriting profitability, agency development, and portfolio management objectives.

The Regional Manager will develop and maintain strong relationships with agents, brokers, principals, indemnitors, and other business partners while exercising significant underwriting authority and ensuring compliance with company underwriting guidelines and risk appetite. The position is highly market-facing and focused on profitable business development, agency management, and underwriting execution.

Key Accountabilities/Deliverables:

Underwriting Leadership

• Serve as lead underwriter for the assigned territory.

• Analyze, evaluate, and approve commercial surety submissions within delegated authority.

• Review and assess financial statements, interim financial reports, work-in-progress schedules, bank agreements, credit reports, tax returns, and other underwriting information.

• Structure and negotiate underwriting terms, collateral requirements, indemnity agreements, and other risk mitigation measures.

• Determine appropriate capacity, pricing, and terms for new and renewal business.

• Monitor portfolio performance and take corrective action as necessary to achieve profitability objectives.

• Participate in large account reviews and referral discussions.

• Maintain underwriting quality and adherence to company guidelines and authority levels.

Customer and Broker Service

• Deliver responsive, solution-oriented service to brokers and insureds. Resolve complex underwriting issues and relationship challenges.

• Maintain a high level of market visibility and accessibility.

• Collaborate with claims, legal, accounting, and operations departments to support business objectives.

• Travel throughout the territory to maintain agency and client relationships.

Leadership and Talent Development

• Recruit, train, mentor, and develop commercial surety underwriters.

• Provide technical underwriting guidance and coaching.

• Assist in establishing underwriting goals and performance expectations.

• Promote underwriting consistency and best practices across the region.

• Participate in succession planning and employee development initiatives.

• Foster a collaborative, performance-oriented culture focused on underwriting excellence and customer service.

Portfolio and Profitability Management

• Own profit and loss results for the assigned region.

• Manage portfolio mix, pricing adequacy, retention, and growth metrics.

• Monitor premium volume, loss ratio, expense ratio, and collection objectives.

• Conduct periodic book reviews to identify trends, opportunities, and emerging risks.

• Evaluate agency performance and manage agency relationships accordingly.

• Recommend strategic actions to improve profitability and operational performance.

• Assist senior leadership with budgeting, business planning, and forecasting.

Marketing and Business Development

• Develop and execute regional marketing and production plans.

• Build and strengthen relationships with retail and wholesale surety brokers. Identify and develop new business opportunities consistent with company risk appetite.

• Conduct regular agency visits and joint sales calls.

• Represent the company at industry events, agency meetings, conferences, and association functions.

• Drive submission flow and increase market visibility throughout the territory. Establish agency business plans and monitor production goals.

• Maintain strong relationships with key distribution partners and strategic accounts.

Technical Knowledge and Understanding:

• Strong technical underwriting expertise, including knowledge of surety principles, financial risk assessment, and bond forms.

• Excellent analytical and decision-making skills, with the ability to assess complex risks and provide solutions

• Effective communication and interpersonal skills for building relationships and managing stakeholder expectations

• Proficiency in underwriting software systems, Microsoft Office Suite, and Adobe.

• Quantitative analysis skills

• Ability to present and negotiate complex agreements with brokers

• Effective time management and organizational skills

• Ability to work independently and perform quality work within deadlines

Experience:

• Bachelor's degree in Business, Accounting, Finance, or related field is required

• Advanced degree or professional certifications (e.g. AFSB, CPCU, etc.) is preferred

• Proven experience (typically 5+ years) in underwriting roles within the surety industry

• Strong financial statement analysis and credit underwriting skills.

• Demonstrated success developing agency relationships and generating profitable growth.

• Strong negotiation, communication, and presentation skills.

• Ability to exercise independent underwriting judgment.

• Proven business development and marketing experience.

• Willingness to travel throughout assigned territory.

Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over work authorization sponsorship now or in the future for this position.
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At Core Specialty, you will receive a competitive salary and opportunities for professional development and advancement. We offer medical, dental, vision, and life insurances; short and long-term disability; a Company-match of 100% of a 6% contribution 401(k) plan; an Employee Assistance Plan; Health Savings Account, Flexible Spending Account, Health Reimbursement Account, and a wellness program