Underwriter Jobs in Maryland
Underwriter jobs in Maryland are consistently active, concentrated in commercial lines, mortgage, and health insurance across the Baltimore metro, Annapolis, and the Maryland suburbs of Washington, D.C. Major employers with longstanding Maryland footprints include CareFirst BlueCross BlueShield, T. Rowe Price, and Transamerica, which together drive steady demand across personal lines, group benefits, and financial guarantee underwriting. Openings run from entry-level commercial underwriting assistants through senior and specialty underwriters covering surety, cyber, and professional liability. Scan the live roles below and apply to whichever ones fit.
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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.
Underwriter
POSITION SUMMARY
Develop and analyze underwriting data to determine if risks meet company-underwriting standards within an assigned territory. Develop and achieve Agency Business plans relative to expected new business growth and renewal retention. Interact with policyholders and/or agents to ensure proper pricing, growth, profitability, and adherence to company policies and procedures.
DUTIES AND RESPONSIBILITIES
- Perform underwriting activities and risk selection process in accordance with company policies and letter of authority.
- Develop and achieve Agency Business Plans regarding new premium growth and renewal retention for assigned agencies.
- Accountable for risk selection, pricing, and file documentation within assigned territory.
- Develop acceptance/rejection, and pricing recommendations on accounts that exceed delegated authority.
- Accountable for achievement of overall loss ratio, pricing, premium and service objectives as established in company/department business plans.
- Actively supports Company Strategies and Departmental Goals.
- Provides timely and accurate information to management regarding status of individual territory.
- Maintain, monitor, and manage assigned book of business utilizing reports or other methods as provided or necessary.
- Conduct agency/customer visits to develop and maintain relationships, resolve issues, generate profitable new business and retain profitable existing accounts.
- Assists in Underwriting audits and management reviews.
- Proactively anticipate and satisfy the needs of internal and external customers by providing superior customer service.
- Bachelor’s degree or equivalent industry experience required.
- 3 to 5 years of related commercial underwriting experience to include Workers’ Compensation.
- Bilingual skills preferred.
- Active pursuit of professional industry certifications / designations CPCU, WCP, AU etc.)
- Good verbal and written communication skills.
- Strong interpersonal skills.
- Basic Computer Skills (Word, Excel, PowerPoint, and Microsoft Outlook).
- High level of independence and organization.
- Customer Service Management
- Practical Knowledge
- Communicating Effectively
- Analytical Thinking/Problem Solving
- Influence Negotiation
- Drive for Results
While performing the duties of this job, the employee is regularly required to sit, use hands to finger, handle or feel objects, tools or controls; reach with hands and arms. The employee is occasionally required to stand, walk, stoop, kneel, crouch or crawl. The employee may occasionally lift up to 30 pounds. Specific vision abilities are required, which includes close vision, peripheral vision and the ability to adjust focus.
WORK ENVIRONMENT
Office Environment. The noise level is usually moderate.
SALARY
$64,605.00-$96,907.00 (per year, commensurate with experience)
Senior Underwriter
POSITION SUMMARY
Develop and analyze underwriting data to determine if risks meet company underwriting standards within an assigned territory. Assist department management with special projects. Serve as Mentor to others within the department.
DUTIES AND RESPONSIBILITIES
- Perform underwriting activities and risk selection process in accordance with company policies and letter of authority.
- Accountable for risk selection, pricing, and file documentation within assigned territory.
- Develop and achieve Agency Business Plans regarding new premium growth and renewal retention for assigned agencies.
- Interact with policyholders and/or agents to ensure proper pricing, growth, profitability and adherence to company policies and procedures.
- Develop acceptance/rejection and pricing recommendations on accounts that exceed delegated authority.
- Provide authority to underwriters and associate underwriters for risks that are outside their delegated authority.
- Accountable for achievement of overall loss ratio, pricing, premium and service objectives as established in company/department business plans.
- Actively support Company Strategies and Departmental Goals.
- Provide timely and accurate information to management regarding status of individual territory.
- Maintain, monitor, and manage assigned book of business utilizing reports or other methods as provided or necessary.
- Conduct agency/customer visits to develop and maintain relationships, resolve issues, generate profitable new business and retains profitable existing accounts.
- Proactively anticipate and satisfy the needs of internal and external customers by providing superior customer service.
- Actively work to design solutions to identified or perceived problems.
- Assist in Underwriting audits and management reviews.
- Keep abreast of the competition, their products, philosophies, distribution systems, and market trends, and communicate such information within the organization.
- Assist supervisors and management on projects or other duties as assigned.
- Provide training / mentoring and orientation to Associate Underwriters and Underwriters, as well as, others within the organization.
- A Bachelor’s degree is required. Industry Experience may be considered as equivalent to this education requirement in conjunction with earned industry professional designations or certifications.
- Required industry related professional designations or certifications. (CPCU, WCP, AU etc.)
- 5 to 8 years of related commercial underwriting experience to include WC Insurance.
- General PC skills. (Word, Excel, PowerPoint, Microsoft Office)
- Bilingual skills preferred.
- Demonstrate technical / industry expertise through knowledge, education and application.
- Demonstrated ability to consistently make sound underwriting decisions on complex or unusual issues.
- Customer Service Management
- Practical Knowledge
- Analytical Thinking/Problem Solving
- Communicating Effectively
- Influence Negotiation
- Collaborative Consulting
- Drive for Results
While performing the duties of this job, the employee is regularly required to sit, use hands to finger, handle or feel objects, tools or controls; reach with hands and arms. The employee is occasionally required to stand, walk, stoop, kneel, crouch or crawl. The employee may occasionally lift up to 30 pounds. Specific vision abilities are required, which includes close vision, peripheral vision and the ability to adjust focus.
WORK ENVIRONMENT
Office Environment. The noise level is usually moderate.
SALARY
$75,358.00-$113,043.00 (per year, commensurate with experience)
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.
See All 22 Underwriter Jobs in Maryland
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Find Underwriter JobsUnderwriter Jobs by City in Maryland
Where Maryland roles are concentrated, by current openings.
Underwriter Job Market in Maryland
A snapshot from current Maryland openings, updated as new roles post.
Who's Hiring



Top Industries Hiring
- Staffing & Recruiting
- Insurance
- Construction & Real Estate
What Maryland Employers Look For
The qualifications that appear most often in underwriter jobs across Maryland.
- Active Maryland property and casualty or life and health insurance license as required
- Bachelor's degree in finance, business, risk management, or a related field
- Two or more years of underwriting experience in commercial, personal, or specialty lines
- Working knowledge of underwriting platforms such as Guidewire or Duck Creek
- CPCU, CUW, or AU designation preferred for mid-level and senior positions
- Strong analytical and credit risk assessment skills with attention to detail
Underwriter Jobs in Maryland: Frequently Asked Questions
How do you become a underwriter in Maryland?
Most underwriters in Maryland start with a bachelor's degree in finance, business, economics, or a related field, then enter the industry through an underwriting trainee or analyst role at an insurer, bank, or specialty firm. Property and casualty or life and health underwriters working on licensed lines must hold the appropriate Maryland insurance producer or underwriter license issued through the Maryland Insurance Administration. Many candidates pursue the CPCU or AU designation through the Institutes to advance into commercial or specialty underwriting.
How much do underwriters make in Maryland?
Underwriters in Maryland earn a median of about $92,120 a year, based on May 2025 Bureau of Labor Statistics wage data, ranging from around $59,520 for the lowest 10% to over $152,690 for the top 10%. Pay rises with experience, specialty, and employer.
Which companies hire underwriters in Maryland?
Maryland underwriter roles are posted by Allianz, Jobot, and The Hartford and others right now, based on current listings on Migrate Mate as of September 2026. Maryland's concentration of health insurers, mortgage lenders, and federal government contractors in the Baltimore-Washington corridor makes it one of the more active mid-Atlantic states for underwriting talent.
Which Maryland cities have the most underwriter jobs?
Baltimore, Hunt Valley, and Fulton have the most underwriter openings in Maryland. Baltimore anchors the market through its large health insurance carriers and financial institutions, while Annapolis draws openings tied to state-regulated insurance activity, and the Maryland suburbs of Washington, D.C., including Bethesda and Rockville, attract mortgage and government-related underwriting roles from employers serving the federal corridor.
Are there remote underwriter jobs in Maryland?
Yes, and more than most fields. About 95% of underwriter openings tied to Maryland are remote or hybrid as of September 2026, reflecting how desk-based and document-driven the work is by nature. Commercial lines, mortgage, and health underwriting roles tend to offer the most remote flexibility, while positions requiring in-person broker or agent relationship management are more likely to require some on-site presence.
How can I get hired as a underwriter in Maryland with little or no experience?
The most realistic entry path is an underwriting assistant or underwriting trainee role, which large Maryland-based insurers like CareFirst BlueCross BlueShield and regional commercial carriers post regularly for candidates without direct underwriting experience. Adjacent roles in claims, insurance customer service, or loan processing at Maryland banks and mortgage companies are a recognized stepping stone. Earning a Maryland insurance producer license before applying, or beginning the AU designation through the Institutes, gives candidates a measurable edge over other applicants at the entry level.
Where can I find and apply to underwriter jobs in Maryland?
You can find and apply to underwriter jobs in Maryland on Migrate Mate, which lists current Maryland openings. Search the available roles, find the ones that match your background and specialty, and apply directly to the positions that fit.
See All 22 Underwriter Jobs in Maryland
Find roles in Maryland that match your experience and apply in just a few clicks.
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