Who We Are

Chesapeake Employers’ Insurance Company is a purpose-driven organization dedicated to improving the lives and livelihoods of our policyholders, injured workers, team members, and the community. As a leading workers' compensation specialty insurer in the mid-Atlantic region, we take pride in being a force for good. Our 350 team members are committed to making a positive impact every day in the lives of all our stakeholders. Join our motivated, professional team as we foster a culture of values, teamwork, innovation, and collaboration. Established in 1914, Chesapeake Employers Insurance, headquartered in Towson, Maryland, has over a century of experience, a strong financial foundation, and an "A" rating from AM Best.

Position Summary:
Serves as the primary contact and subject matter expert for the multi-state book of business, leading underwriting evaluation and pricing decisions for complex new and renewal accounts within delegated authority. Assesses risk characteristics to appropriately segment and apply accurate rates, pricing structures, and terms to ensure alignment with company guidelines, profitability objectives, and service expectations, while maintaining thorough file documentation. Utilizes underwriting exposure and portfolio data to support sound pricing structures, identifies growth opportunities, and provides referral support and recommendations for accounts exceeding authority. Partners with agents, policyholders, and internal stakeholders to resolve issues, strengthen agency relationships, support departmental initiatives, and contribute to ongoing process and system improvements.

Duties and Responsibilities:
· Contributes to the achievement of established department goals and objectives; adheres to departmental policies, procedures, quality, and safety standards as applicable, and consistently exhibits Chesapeake’s Values and Behaviors.
· Leads the evaluation and underwriting of new and renewal multi-state business, applying company guidelines to appropriately segment risks and determining accurate pricing and profitability outcomes.
· Performs underwriting activities focused on exposure evaluation, risk differentiation, and pricing application in accordance with company policies and letter of authority.
· May act as a Team Lead in the absence of the supervisor or manager.
· Conducts policy and underwriting file reviews to ensure accuracy, consistency, and adherence to standards.
· Interacts with policyholders and/or agents to ensure proper pricing, growth, profitability, and adherence to company policies and procedures.
· Develops pricing recommendations on accounts that exceed delegated authority, and when necessary by exception, recommends risk declination for non-Maryland exposures.
· Provides authority to senior underwriters, underwriters, and associate underwriters for risks outside their delegated authority.
· Works closely with IT and other internal departments to resolve technical, operational, and system-related issues.
· Provides timely and accurate information to management regarding territory status.
· Maintains and manages multi-state book of business, with emphasis on portfolio balance and long-term profitability.
· Conducts agency and customer visits to develop and maintain relationships, resolve issues, generate profitable new business, and retain profitable existing accounts.
· Designs solutions to identify or perceive underwriting or operational issues.
· Monitors competitive products, distribution systems, and market trends and communicating insights internally to support pricing and underwriting strategies.
· Assist supervisors and management on projects or other duties as assigned.
· Provides training, mentoring, and orientation to underwriting staff and others within the organization.
· Other duties and project work as assigned.

Knowledge, Skills and Abilities:
· Demonstrates advanced proficiency in utilizing and leveraging technologies, tools, and platforms, including Microsoft tools.
· Demonstrates strong technical and industry expertise through knowledge, education, and application of underwriting and pricing principles.
· Applies sound judgment when evaluating complex exposures and translating risk characteristics into appropriate pricing outcomes.
· Ability to develop, build, and maintain strong internal and external relationships.
· Strong analytical, organizational, and problem-solving skills.

Minimum Qualifications:
· Bachelor’s degree required; relevant industry experience may be considered in lieu of a degree when combined with appropriate professional designations or certifications.
· Required industry-related professional designations or certifications (CPCU, WCP, AU, or other industry-related credentials).
· At least five (5) years of senior commercial underwriting experience, including workers’ compensation.
· Effectively utilizes technologies and tools, including Microsoft 365 and role-specific platforms, to support productivity and efficient work practices.

Preferred Qualifications:
· Experience providing training, mentoring, or orientation to underwriting staff.
· Experience supporting multi-state underwriting or complex commercial accounts.

Physical Demands:
This job description is intended to describe the general nature and level of work being performed. It is not an exhaustive list of all responsibilities, duties, and skills required. Reasonable accommodation may be made to enable individuals with disabilities to perform the essential functions. While performing the duties of the job, the teammate is regularly required to sit; use hands and fingers; handle or feel objects, tools or controls; and reach with hands and arms. The teammate is occasionally required to stand, walk, stoop, kneel, crouch or crawl and may occasionally lift up-to 30 pounds. Specific vision abilities required include close vision, peripheral vision, and the ability to adjust focus. When in office, able to work in an office environment where the noise level is moderate.

What We Offer

We offer a competitive benefits package that includes health, vision, and dental coverage, a robust PTO plan, an 8% employer contribution to retirement regardless of team member contribution, educational assistance, and opportunities to participate in team member appreciation events. Additionally, we provide STD, LTD and group life insurance 1X a team members salary. You'll also enjoy free tickets to community attractions, all part of our commitment to providing a high quality of work life. You will have the flexibility to thrive in a hybrid work environment and an opportunity to participate in development and volunteer programs.