This page tracks remote underwriter openings that are location-eligible for Maryland.
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Role Description Are you a strategic underwriting leader who thrives on developing talent and shaping portfolio performance? MEM Insurance is seeking an experienced Underwriting Manager to lead and elevate our underwriting team. In this role, you will guide the team toward an appetite-led, portfolio-driven approach to decision-making—ensuring that every underwriting decision supports profitable growth and long-term success. You will serve as the critical bridge between leadership strategy and day-to-day execution, translating organizational direction into clear, actionable guidance for your team. This is a highly visible leadership opportunity for someone who enjoys building underwriting excellence, engaging with market and portfolio data, and helping others grow their judgment and confidence. Essential Duties and Responsibilities - Underwriting Leadership and Strategy - Translate MEM’s underwriting appetite and strategic direction into clear guidance that drives consistent, portfolio-aligned decision-making. - Lead the team to think beyond individual transactions, ensuring underwriting decisions reflect broader portfolio outcomes. - Monitor book-of-business composition, identifying trends, concentrations, and opportunities for proactive strategic adjustments. - Contribute to underwriting strategy discussions using insights from market conditions, loss trends, and portfolio performance. - Coach underwriters to strengthen judgment and decision-making aligned to performance and profitability goals. - Operational Leadership - Oversee daily underwriting operations to ensure alignment with department objectives and broader business goals. - Manage risk selection, pricing, and reinsurance decisions within authority to maintain quality and profitability. - Balance workload across the team to deliver strong service levels and consistent results. - Partner with underwriting leadership to ensure consistent execution of best practices across the organization. - Underwriting Quality and Governance - Ensure underwriting decisions align with company guidelines, authority levels, and compliance expectations. - Analyze historical loss data and financial trends to inform risk selection and portfolio strategy. - Support the development and evolution of underwriting guidelines based on market and business needs. - Lead quality assurance efforts by reviewing underwriting work, identifying improvement opportunities, and driving corrective actions. - Maintain strong documentation standards and audit readiness. - People Leadership and Talent Development - Develop underwriting judgment within the team, empowering individuals to make confident, independent decisions. - Create tailored development plans that support growth at every stage of an underwriter’s career. - Lead meaningful performance conversations focused on decision quality, consistency, and alignment with strategy. - Identify hiring, promotion, and role alignment opportunities that strengthen overall team capability. - Cross-Functional Collaboration - Build strong relationships with agency partners and Sales Executives to grow in-appetite business. - Collaborate across departments—including Safety, Claims, Finance, and Sales—to drive aligned outcomes. - Lead coordination on complex accounts through account reviews and cross-functional engagement. - Represent underwriting with professionalism and clarity to internal and external stakeholders. - Analytical and Strategic Contribution - Provide insights and recommendations on profitability, premium planning, and portfolio performance. - Support strategic initiatives that enhance underwriting operations and competitiveness. - Contribute to improvements in underwriting tools, systems, and processes. Qualifications - Bachelor’s degree in Business Administration, Insurance, Finance, or related field (or equivalent experience). - CPCU or AU designation preferred. - Valid driver’s license required. - 6+ years of underwriting experience, with property and casualty experience preferred. - Demonstrated ability to lead, develop, and motivate a team. - Strong communication skills with the ability to translate complex concepts into clear direction. Benefits - Health Plans: Medical, Dental, and Vision, including fertility benefits, fully paid preventative care, and adult orthodontia. - Employer-Paid Life and Disability Benefits: Life Insurance (3x base salary), AD&D, Short and Long-term Disability. - Wellness and Recognition Program: Employer-paid incentives for employees and spouses. - Flexible Spending Account and Dependent Care options. - Health Savings Account: Generous employer contribution. - Time Away from Work: Generous PTO, 11 Holidays + 4 Early Releases, 16 Hours Volunteer Time Off, 20 Days Paid Parental Leave, Marriage, Bereavement, and Jury Duty leave. - Employee Assistance Programs. - 401k Retirement Plan: Employer match and profit sharing. - Adoption Assistance and Tuition Assistance.
• Act as a trusted advisor and thought partner to casualty leadership • Serve as a key liaison between the Casualty Line of Business and other business units, ensuring alignment in underwriting strategies, priorities, and execution • Help underwriters craft coverage with precision, clarity, and intent • Influence the next generation of casualty products and capabilities • Strengthen underwriting discipline while enabling smart growth in evolving markets • Engage directly with underwriting teams through in-person collaboration, field travel, and hands-on development • Lead and execute casualty product strategy initiatives aligned to profitability, growth, and long-term portfolio objectives • Partner with Product, Actuarial, Claims, and Business Units to design, evolve, and implement casualty product offerings and strategic roadmaps • Translate market trends, emerging risks, and legal/regulatory shifts into actionable underwriting, product, and distribution strategies • Champion innovation in underwriting approach, product design, and participation in alternative distribution models • Collaborate with corporate underwriting leadership to refine underwriting guidance, best practices, and authority frameworks, including administration of underwriting authority levels • Mentor underwriters and leaders to elevate technical expertise, judgment, and decision quality.
WPS, a health solutions company, is a leading not-for-profit health insurer and federal government contractor headquartered in Madison, Wisconsin. WPS offers health insurance plans for individuals, families, seniors, and group health plans for small to large businesses. We process claims and provide customer support for beneficiaries of the Medicare program and manage benefits for millions of active-duty and retired military personnel across the U.S. and abroad. WPS has been making healthcare easier for the people we serve for nearly 80 years. Proud to be military and veteran ready. WPS’ culture is where the great work and innovations of our people are seen, fueled, and rewarded. We accomplish this by creating an open and empowering employee experience. We recognize the benefits of employee engagement as an investment in our workforce—both current and future—to effectively seek, leverage, and include differing and unique perspectives that fuel agility and innovation on high-performing teams. This results in people bringing their authentic selves to work every day in an organization that successfully adapts to business changes and new opportunities.
Role Description The Underwriting Assistant is responsible for supporting the underwriter with quotes, new business and existing business. This role includes: - Data collection - Quote preparation - Documentation management - Ensuring compliance with internal guidelines and regulatory requirements - Reviewing and requesting missing paperwork for new business, renewals, and changes - Providing clear communication with internal teams regarding requirements and changes for groups - Supporting underwriters in making timely, accurate risk decisions and maintaining a smooth workflow Qualifications - High School Diploma or GED or equivalent experience - 1 or more years of experience in health insurance, underwriting, or related administrative support role - Proficiency with Microsoft Excel, Word, and Outlook - Detail-oriented with a commitment to data accuracy - Strong organizational and time management skills - Strong written and verbal communication skills - Ability to handle confidential information appropriately - Familiarity with group health plans, medical underwriting practices, and industry terminology preferred - Experience with health plan quoting tools or underwriting systems is preferred Requirements - Enjoy reviewing quoting data for completeness and requesting additional information as necessary - Prepare and index all documents into the underwriting system - Upload data to the web tool to aid in underwriting - Prepare renewal packets including the correct addendums and SBCs for mailing - Complete group set-up and configuration sheets for new groups, renewal groups, and changes - Ensure information is entered accurately into the underwriting system for routing to other departments - Create rate calculators for renewal and quotes - Maintain tracking systems for groups requesting quotes and renewal groups - Research information on a group or individuals within a group to aid in the underwriting process - Interface with sales staff and other departments to resolve rate and benefit issues - Review all new groups to ensure they are not on the Specially Designated Nationals List (SDN) - Assign group numbers - Provide renewal reports to the assigned underwriter to support renewal rate decisions - Ensure compliance with internal guidelines and applicable regulations (i.e., ACA, HIPAA) Benefits - Remote and hybrid work options available - Prorated Holiday Pay and On-Demand PTO
Great American Insurance Group, a subsidiary of American Financial Group, is a Cincinnati, Ohio-based insurance company specializing in property and casualty in
Title: Medical Stop Loss Underwriter Location: United States Full time job requisition id R9126 Be Here. Be Great. Working for a leader in the insurance industry means opportunity for you. Great American Insurance Group's member companies are subsidiaries of American Financial Group. We combine a "small company" culture where your ideas will be heard with "big company" expertise to help you succeed. With over 30 specialty and property and casualty operations, there are always opportunities here to learn and grow. At Great American, we value and recognize the benefits derived when people with different backgrounds and experiences work together to achieve business results. Our goal is to create a workplace where all employees feel included, empowered, and enabled to perform at their best. Great American Employer Health Solutions (EHS) offers medical stop loss coverage that helps small to mid‑sized employers self‑fund their employee health plan with confidence by protecting their plans from high-cost, unexpected claims. Our Level Funded Plus program provides employers with the tools to self‑fund their benefits more easily, including access to quality networks and health plan partners, flexible plan design options, and integrated medical stop loss coverage. We are looking for a Medical Stop Loss Underwriter to work remotely. This role is an excellent opportunity for individuals who are inquisitive, adaptable, and ready to accelerate their careers in a transformative startup environment. The person in this position will gain significant exposure to underwriting, data systems, and group performance analysis. This position will play a key role in the underwriting function, ensuring the organization has the necessary insights to understand the potential risks of groups. In addition to Underwriting, this role will also focus on Data Systems Support and Group Performance Analysis. Essential Job Functions and Responsibilities - Underwriting Support - Assess the risk factors of potential clients. - Assist with storing specific data elements, and policy issuance, while maintaining a strong working relationship with clients. - Evaluate the risk profiles of groups using EHS's machine learning/AI software to determine their viability and profitability. - Data collection- collect, organize, and analyze data from various sources to support underwriting decisions and contribute to risk modeling. - Works closely with other team members to ensure a comprehensive understanding of program stacks and cost containment measures. - Data Systems Support - Assists with organizing and maintaining our data systems, ensuring the integrity, accuracy, and security of our data. - Tasks may include data analysis, troubleshooting system problems, and data entry. - Group Performance Analysis - Collaborates closely with our account management team by providing research and analytical support. Job Requirements - Bachelor’s degree is preferred. - Generally, 2-5 years of medical stop loss underwriting experience. - Must have strong critical thinking skills and the ability to understand and integrate complex data. - Prior experience with risk assessments is preferred. Business Unit: Great American Employer Health Solutions Salary Range: $80,000.00 -$100,000.00 Benefits: We offer competitive benefits packages for full-time and part-time employees*. Full-time employees have access to medical, dental, and vision coverage, wellness plans, parental leave, adoption assistance, and tuition reimbursement. Full-time and eligible part-time employees also enjoy Paid Time Off and paid holidays, a 401(k) plan with company match, an employee stock purchase plan, and commuter benefits. Compensation varies by role, level, and location and is influenced by skills, experience, and business needs. Your recruiter will provide details about benefits and specific compensation ranges during the hiring process.
Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we’re one of the largest and financially strongest mutual insurance companies in the United States. We’re rated A+ by A.M. Best, the industry's leading rating authority. Get ready to own your future at Sentry. Opportunities await! Casey Van Der Geest Casey.VanDerGeest@sentry.com Equal Employment Opportunity Sentry is an Equal Opportunity Employer. It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.
Role Description This role markets Commercial Lines products, builds agency partnerships, leads underwriting for new/complex business, manages growth and profitability, and maintains market visibility. The preferred candidate for this position will reside in the Jackson, MS - Mobile, AL - Birmingham, AL triangle with travel required in and around that territory. The Territory Underwriter Specialist will be responsible for agent and broker relationships. In addition, you’ll: - Solicit accounts through select agents and brokers - Evaluate, underwrite, and price prospective accounts to select independent agents - Serve as the primary contact with assigned agents and brokers - Provide comprehensive sales expertise to increase production through agency channels - Work with assigned agents and brokers on the coordinating of resolutions Qualifications - Bachelor’s degree or equivalent work experience - Minimum of 5 years related work experience, with multi-line middle market underwriting experience handling accounts in construction, manufacturing, wholesale, real estate, and service industries preferred - Knowledge of the Mississippi and Alabama marketplace, and existing or past relationships with larger independent agents preferred - Previous technical insurance experience, preferably with sales - Experience with underwriting large complex accounts - Exceptional communication and relationship building skills - Strong business and pipeline development skills - Ability to meet travel requirements as you’ll be prospecting new business opportunities in an agent office; meeting with insureds during safety inspections, and participating in mid-year claims review meetings - Ability to travel and have a valid driver’s license with the ability to maintain an acceptable motor vehicle record Benefits - Company car with gas card - 401(K) plan with a dollar-for-dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future - Continue your education and career development through Sentry University (SentryU) and utilize our Tuition Reimbursement program - Generous Paid-Time Off plan for you to enjoy time out of the office as well as Volunteer-Time off - Group Medical, Dental, Vision, Life insurance, Parental leave, and our Health and Wellness benefits to encourage a healthy lifestyle - Well-being and Employee Assistance programs - Sentry Foundation gift matching program to encourage charitable giving
Apply → Pass qualification(s) → Join a project → Complete tasks → Get paid. Project time expectations: Tasks are estimated to require around 10–20 hours per week during active phases, based on project requirements; This is an estimate, not a guaranteed workload, and applies only while the project is active. Note: Rates vary based on expertise, skills assessment, location, project needs, and other factors. Higher rates may be offered to highly specialized experts. Lower rates may apply during onboarding or non-core project phases. Payment details are shared per project.
Role Description Mindrift connects specialists with project-based AI opportunities for leading tech companies, focused on testing, evaluating, and improving AI systems. Participation is project-based, not permanent employment. What this opportunity involves: - Evaluate AI-generated mortgage underwriting decisions across loan types (conforming, jumbo, FHA, VA, cash-out refinance); - Create test cases involving qualifying income calculations for self-employed borrowers using Schedule C, K-1, and Schedule E; - Draft and audit conditional approval letters and adverse action notices for Reg B / ECOA compliance; - Distinguish Fannie Mae / Freddie Mac selling guide rules from lender overlays in jumbo and non-conforming loan scenarios; - Document problem statements clearly and provide verified correct answers. Qualifications - Degree in Finance, Economics, Business Administration, Accounting, Real Estate, or any related field; - 3+ years of mortgage, lending, real estate, or financial services experience; - Current or recent experience in underwriting & origination or adjacent roles; - Ability to calculate qualifying income for self-employed borrowers from IRS Forms 1040, Schedule C, Schedule E, and K-1; - Deep familiarity with Fannie Mae / Freddie Mac selling guides and knowledge of Reg B, Reg Z, and TRID disclosure timing rules; - Strong written English (C1+). Requirements - This opportunity is a good fit for mortgage underwriters and loan origination professionals open to part-time, non-permanent projects. Benefits - Compensation: Contributors can earn up to $60 per hour equivalent, depending on their level and pace of contribution. - Compensation varies across projects depending on scope, complexity, and required expertise. - Please note that other projects on the platform may offer different earning levels based on their requirements. Company Description Apply → Pass qualification(s) → Join a project → Complete tasks → Get paid Project time expectations: For this project, tasks are estimated to require around 10–20 hours per week during active phases, based on project requirements. This is an estimate, not a guaranteed workload, and applies only while the project is active.
First American is on a mission to deliver a variety of real estate-focused services and solutions. As an employer, First American has been recognized for its ex
Title: Commercial Underwriting Manager Location: United States Job ID R056548 Category Underwriting Employment Type Full Time Who We Are Join a team that puts its People First! As a member of First American's family of companies, National Commercial Services provides single-point service for simple to multi-property/multi-state national commercial real estate transactions. Since 1889, First American (NYSE: FAF) has held an unwavering belief in its people. They are passionate about what they do, and we are equally passionate about fostering an environment where all feel welcome, supported, and empowered to be innovative and reach their full potential. Our inclusive, people-first culture has earned our company numerous accolades, including being named to the Fortune 100 Best Companies to Work For® list for eleven consecutive years. We have also earned awards as a best place to work for women, diversity and LGBTQ+ employees, and have been included on more than 50 regional best places to work lists. First American will always strive to be a great place to work, for all. For more information, please visit www.careers.firstam.com. What We Do Manages the day-to-day activities of a team of Underwriters and may manage title professionals and support personnel that provides underwriting support and expertise to company personnel, agents, and customer(s), related to the issuance of real estate title insurance commitments and policies. Utilizes underwriting standards and guidelines within delegated authority limits, to underwrite the issuance of title insurance and provide guidance in the performance of real estate settlement services. HOW YOU’LL CONTRIBUTE - Manages and sets priorities of the daily operations of a large functional area or department. - Manages a group of professionals (typically skilled exempt and non-exempt level employees) who have responsibility for operations and project outcomes. Provides direct and indirect supervision of teams. - Contributes to project reviews and approves detailed designs and cost estimates for projects. - Participates in long-range departmental planning and provides input to operational decisions and to clarify or modify project plans, and/or schedule requirements. - Writes and conducts employee performance reviews and provides ongoing performance feedback through coaching. Makes hiring and compensation recommendations. May get input from Senior Management/Executive Management. - Other duties as assigned WHAT YOU’LL BRING Required Education, Experience, Certification/Licensure - Juris Doctor preferred. Bachelor’s degree or equivalent combination of education and experience - 5-7 years of directly related experience in the Title Industry - 3-5 years demonstrated experience in a supervisory or management role preferred KNOWLEDGE, SKILLS, AND ABILITIES (KSAs) - Successful track record designing, developing, and executing complex projects in area of functional expertise. - Ability to establish and maintain effective working relationships at the Management level across functional groups and business units. Adeptness to influence the thinking of, or gain acceptance from, others in sensitive situations, using influence and preventing damage to the relationships. - Strong capacity to communicate the function’s vision and the department’s direction and set aligned goals. Provides resources and creates systems to measure results. Familiar with competitor, financial and industry dynamics. - Actively recruits, retains, and develops talent and holds employees accountable for results. Leads change, manages conflict, and fosters collaboration. - Drives and models customer loyalty, manages customer expectations, solicits customer feedback, and ensures commitments are met. - Provides others with reliable information and delivers informative and persuasive presentations. Uses good listening skills and negotiates effectively. - Collaboratively engages with leaders to create, identify, and implement solutions to further effectiveness of the business. ** Note that the following statements only apply to candidates who will be working from an unincorporated area within Los Angeles County. ** First American will consider for employment all qualified applicants, including those with arrest or conviction records, in a manner consistent with the requirements of applicable state and local laws (e.g., the Los Angeles County Fair Chance Ordinance for Employers and the California Fair Chance Act). First American intends to conduct a review of an applicant’s criminal history in connection with a conditional offer. First American reasonably believes that a criminal history may have a direct, adverse and negative relationship with the following material job duties for this position potentially resulting in the withdrawal of the conditional offer of employment: handling of confidential, proprietary or trade secret information belonging to First American or its customers, administrating or facilitating financial transactions, and the ability to meet customer-imposed criminal history requirements. What We Offer By choice, we don’t simply accept individuality – we embrace it, we support it, and we thrive on it! Our People First culture is inclusive for all employees - not just because it's the right thing to do, but because it's the key to our success. We are proud to foster an authentic and inclusive workplace For All. You are free and encouraged to bring your entire, unique self to work. First American is an equal opportunity employer in every sense of the term. Based on eligibility, First American offers a comprehensive benefits package including medical, dental, vision, 401k, PTO/paid sick leave and other great benefits like an employee stock purchase plan. Pay Range: $129,300.00 - $172,300.00 Annually This hiring range is a reasonable estimate of the base pay range for this position at the time of posting. Pay is based on a number of factors which may include job-related knowledge, skills, experience, business requirements and geographic location.
• Lead the go-to-market distribution strategy and commercial underwriting for Energy. • Support the Energy team in managing a portfolio of new business submissions and/or renewal submissions specifically for the Energy portfolio. • Analyze and provide policy structure and premium rates for submissions. • Help develop customer relationships, cultivate and manage commercial Energy team, direct sales force and/or broker relationships. • Provide the highest quality of customer service. • Assess commercial underwriting risk, review standing of the portfolio. • Ensure compliance while driving the energy business towards Allianz Trade’s retention, growth and profitability objectives. • Provide the highest possible level of customer service to internal and external customers. • Support the team in maximizing approvals for the portfolio of policyholders. • Manage a portfolio of non-cancellable and cancellable clients. • Manage and support customer relationships with brokers and Energy leadership. • Support and drive revenue and growth goals. • Mentor and provide guidance / training for team members. • Work independently on other tasks assigned. • Responsible for a dedicated portfolio, steering and providing a pro-active exceptional service level, by regularly meeting customers and brokers. • Contribute to support Commercial in steering customers loss ratio and implement necessary actions to ensure or restore profitability of portfolio. • Take responsibility on projects and initiatives as assigned. • Build relationships with other core functions. • Attend Association and industry conferences and networking events. • Understand and remain current on Energy specific contracts and updates in the market.
• Provide individual Underwriter coaching, mentoring, and training on the expectations, processes, guidelines, system work (Encompass), etc., escalating questions as needed for clarification • Serve as the primary point of contact for all questions, clarification, and instruction for Underwriters • Ensure Underwriters understand, apply, and grow their knowledge base of guidelines, processes, and procedures at CCM • Complete CTC reviews until Underwriters have earned lending authority • Review the CR Lending Authority, ACES, Denial, Suspense, Failed, and 2nd Tier Review Pipeline reports daily • Provide valid findings, training, and coaching issues weekly to the VP • Complete at least 2 spot reviews per week on files not reviewed by another department/team (i.e. QC, CRUM, etc.) • Assist with the review of reports and findings regarding Underwriter quality as needed • Manage the pipeline making sure loans for all areas are within SLA, and all loans placed in any external Underwriter status are for no more than 24 hours (for branch rebuttal, 72 hours) • Communicate all load balancing, designated underwriting assignments, and rush/priority reviews (VIP, Transition, etc.) to the Production Coordinators • Assist with loan level production (underwriting, clearing conditions) based on staffing/volume needs • Review and complete non-health/safety escrow holdbacks • Review loan scenarios as needed/required • Review post-closing/credit risk findings to identify and determine training needs • Conduct new branch welcome calls and existing branch calls as needed (daily, weekly, monthly) • Report on Underwriter final bonus numbers; communicate to the VP • Interview prospective Underwriters for hire • Review and approve timecards and PTO requests • Attend weekly meetings with the VP and Monthly National Underwriting department calls conducted by the SVP of Underwriting; hold bi-weekly team meetings with direct reports
• Ability to underwrite conventional and government loans (FHA, VA). • Maintain and report underwriter bonus. • Provide guidance and solutions to underwriting team and branches for complex underwriting scenarios and escalations. • Assist in special projects and training as designated by underwriting management. • Communicate with branches on escalations and escalated scenarios. • Perform second level reviews as designated by senior underwriting management. • Work with underwriting team to maintain standard service level agreements. • Monitor underwriting pipeline to ensure productivity and adherence to set SLAs. • Provide mentoring and coaching to underwriting staff as identified or required by senior management. • Utilize problem solving, judgement, knowledge, and experience to effectively remedy loan level issues. • Manage department reports. • Manage a team consisting of approximately five to ten individuals. • Communicate effectively with operations and sales staff to maintain a high level of customer service via phone and email. • Perform other related duties as assigned by management.
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