Remote | Senior Insurance & Underwriting Evaluation Specialist $55-$75/hour
$55 - $75 per hour24-Mag Llc
- Remote job
We are sharing a specialised full-time consulting opportunity for US-based insurance professionals with deep experience in underwriting, claims, actuarial analysis, risk management, and structured evaluation of AI-generated outputs. This role supports a high-impact generative AI initiative focused on improving how advanced models reason through real-world insurance scenarios. Selected professionals will design rigorous domain-specific tasks, evaluate model outputs against structured criteria, develop scoring frameworks, and provide practical feedback grounded in senior-level underwriting, claims, and risk‑assessment experience. Key Responsibilities Insurance Domain Guidance Guide research and engineering teams on underwriting, claims, actuarial analysis, policy interpretation, and risk‑assessment concepts Identify gaps in model understanding across coverage decisions, loss evaluation, pricing, claims handling, and insurance operations Apply practical insurance judgment to complex scenarios involving policyholders, exposures, financial risk, and regulatory considerations Ensure insurance tasks reflect realistic professional decisions and industry standards Insurance Task & Solution Development Design challenging, domain-relevant tasks grounded in real underwriting, claims, actuarial, or risk‑management practice Write accurate, well‑reasoned solutions covering insurance analysis and decision‑making scenarios Develop problems requiring technical judgment, risk evaluation, policy interpretation, and assessment of competing considerations Ensure tasks are clear, internally consistent, and suitable for structured evaluation AI Output Evaluation Evaluate AI-generated insurance responses against established rubrics and scoring criteria Assess correctness, professional judgment, reasoning quality, relevance, and practical applicability Compare alternative outputs and determine which response provides the stronger insurance analysis Identify factual errors, unsupported assumptions, weak risk reasoning, and incomplete conclusions Provide clear written feedback that supports improvements in model behaviour Rubric Development & Quality Calibration Develop and refine evaluation guidelines for underwriting, claims, actuarial, and risk‑management tasks Define scoring criteria covering technical accuracy, professional judgment, reasoning, and decision quality Participate in calibration activities with other insurance specialists Collaborate across teams to maintain consistency and accuracy throughout the training data Ideal Profile Strong candidates may have: At least 8 years of dedicated professional experience in insurance Senior‑level expertise in underwriting, claims, actuarial work, risk management, or a related area Experience working within a recognised insurer, broker, consultancy, financial‑services organisation, or comparable institution Prior hands‑on experience evaluating LLM or AI‑generated outputs using structured rubrics or scoring criteria Demonstrable career progression into senior, management, director, vice president, or comparable leadership responsibilities Strong professional judgment and the ability to assess complex insurance decisions Excellent written and verbal communication skills Reliable availability for at least 35 hours per week during weekdays Educational Background A degree in insurance, actuarial science, finance, economics, mathematics, business administration, risk management, or a related field is highly relevant Graduate‑level education in actuarial science, finance, business, analytics, or risk may be helpful Equivalent senior professional experience in underwriting, claims, or insurance operations may also be considered Professional credentials such as CPCU, ACAS, FCAS, ARM, AIC, or comparable qualifications may be valuable Nice to Have Experience across property and casualty, life, health, commercial, specialty, or reinsurance markets Background in complex underwriting, claims investigation, pricing, reserving, or portfolio risk Experience creating structured scoring rubrics, evaluation guidelines, or quality frameworks Familiarity with model training, human‑feedback workflows, annotation, or AI quality assurance Strong understanding of policy language, coverage interpretation, risk selection, and claims decision‑making Experience reviewing underwriting files, claims assessments, actuarial analyses, or risk reports Previous collaboration with product, analytics, legal, compliance, research, or technical teams Why This Opportunity Apply senior insurance expertise to an advanced generative AI initiative Influence how AI systems reason about underwriting, claims, and risk Design and assess challenging insurance problems grounded in practical industry experience Collaborate with technical teams and experienced insurance specialists Join a full‑time remote engagement with competitive hourly compensation Contract Details Full‑time W‑2 contingent employment arrangement Fully remote role available to candidates based in the United States Expected commitment of at least 35 hours per week during weekdaysCompetitive rates between $55–$75 per hour depending on expertise and project scope Prior experience evaluating AI or LLM outputs against structured rubrics is required Applicants should clearly describe relevant AI evaluation experience in their application Immediate availability is preferred Work may include onboarding, specialty calibration, task development, and ongoing quality review Project scope and duration may be adjusted according to programme requirements and performance About the Platform This opportunity is available through 24-MAG LLC. We connect experienced professionals with remote consulting opportunities across technical, evaluation, and project‑based workstreams. #J-18808-Ljbffr 24-Mag Llc
$107.2k - $146.8k
Summit provides independent insurance agents and their clients... ...you turn to when you need a specialist who not only knows workers... ...Leads the evaluation and underwriting of new and renewal business... ...field role in Virginia. #LI-Remote Job Requirements Education...Remote workSeniorFull timePart timeSeasonal work$100k - $110k
...assistance 401(k) Health insurance Retirement plan 4... ...job as a Safety Specialist? Consider joining... ...with our Underwriting and Claims Departments... ...inspections. Evaluate, customize, and develop... ...consists of 37.5 hours, and we close on... ...Location: Hybrid remote in Saint Paul, MN...Remote workSeniorFull timeWork from homeHome officeNight shift$75k - $125k
...currently looking for an Underwriting or Underwriting Specialist within the Direct... ...role independently evaluates new business and... ...rating manual rules, and insurance laws and regulations... ...Specialist is $75,000.00 -$125,000.00... ...- Overland Park Remote Working: Hybrid Schedule...Remote workFull timeTemporary workApprenticeshipWork at officeLocal areaVisa sponsorship$100k - $130k
...leading national insurer with a strong reputation... ..., cutting-edge underwriting practices, and a... ...generous PTO Hybrid/remote flexibility to... ...just click Apply. Seniority level Seniority level... ...ago Chicago, IL $55,000.00-$70,000.00... ....00-$90,000.00 10 hours ago Chicago, IL $6...Remote workSeniorFull time$49 - $53 per hour
...Overview Reporting to the Underwriting Manager, this position is responsible for evaluating, analyzing and... ...stakeholders and serving as a senior resource to support... ...Range: $49.00-$53.00 per hour Compensation within this... ...with employer match Location: Remote #J-18808-Ljbffr...Remote workSeniorHourly pay$60k - $125k
...hire an E&S Property Underwriter for our Property... ...for their insurance needs. Using a... ...approach to exposure evaluation, risk assessment and... ...Underwriting or Underwriting Specialist level. The hiring... ...Specialist is $75,000.00 - $125,000... ...AM - New York Remote Working: Hybrid...Remote workFull timeTemporary workApprenticeshipCurrently hiringWork at officeLocal areaVisa sponsorshipFlexible hours3 days per week$85.04k - $162.55k
...USAA roles may offer remote or hybrid flexibility... ...Policy and Performance Underwriter Senior - Property.This role... ...data to proactively evaluate and recommend changes... ...industry practices, insurance policy contracts, trends... ...16 paid volunteer hours, and various wellness...Remote workSeniorFull timeH1bWork at officeHome office$75k - $85k
...Republic Risk Management SENIOR EVENTS SPECIALIST Location: Brookfield,... ...4 days onsite, 1 day remote once fully trained... ...Management (ORRM), we believe insurance is more than managing... ...life: Salary Range: $75,000 - $85,000... ...Referral Bonus Program 37.5-hour standard work week...Remote workSeniorHome office- ...and detail-oriented VA Underwriter to join our growing... ...-earner borrowers • Evaluate appraisals and collateral... ...This is a full-time remote opportunity for candidates... ...Our standard working hours are Monday to Friday,... ..., dental, vision insurance, and 401(k). Take the...Remote workSeniorFull timeSelf employmentWork at officeMonday to Friday
- ...new business submissions and evaluating the risk for referral to our... ...and assisting renewal underwriters in retaining business. Essential... ...to the Special Risk Insurance Managers culture. Responsible... ...commitments; commits to long hours of work when necessary to reach...Remote workSeniorContract workWork at officeImmediate start
- ...Securian Financial Group is seeking a Life Underwriting Consultant for a remote role based in Minnesota. You will evaluate life insurance applications, assess medical and financial risks, and determine appropriate classifications within authority limits. The role emphasizes...Remote work
$96k - $136k
...we are At Intact Insurance Specialty Solutions,... ...an opportunity for a Senior Underwriter to join our Crime & Fidelity... ...schedule or located remotely nationwide. Under... ...accordingly. Monitors and evaluates results of assigned... ...matters more than hours in the office. We are...Remote workSeniorFull timeWork at officeFlexible hours- Tokio Marine HCC is seeking a Senior Underwriter with Artisan E&S experience to join a distributed, high-performing team.... ...relationships, and profitable book management across a remote-first environment. You will evaluate new and renewal applications, apply underwriting...Remote jobSenior
- ...Excess Liability Underwriter Our client's Excess Liability Division... ...flexibility to work one day remotely. Essential Job Functions... ..., structure, and terms. Evaluate and manage complex renewals,... ...completion of a professional insurance designation preferred....Remote workSeniorNight shift
- ...for assigned high-volume territory with a high level of underwriting authority Evaluates and analyzes highly complex accounts for risk selection... ...& Experience: Bachelor's degree, preferably in insurance or business administration Five years of experience in...Remote workSeniorWork at officeLocal area
- ...As the Senior Underwriter you will evaluate, analyze and price risks associated with excess auto liability coverage... ...guidelines and objectives.Develop insurance proposals, process binders, approve... ...for this position.#LI-Hybrid#LI-Remote-At Core Specialty, you will receive...Remote workSeniorTemporary workFlexible hours
$75k - $165k
...Zurich is seeking an Underwriting Specialist OR Executive Underwriter, Large Property... ..., rating manual rules, and insurance laws and regulations.... ...range for this position is $75,000.00 - $165,000.00. The proposed... ...Francisco, AM - Seattle Remote Working: Hybrid Schedule:...Remote workFull timeTemporary workApprenticeshipWork at officeLocal areaVisa sponsorshipFlexible hours3 days per week$75k - $165k
...Underwriting Specialist OR Executive Underwriter - Large Contract Surety 1371... ...areaOR Zurich Certified Insurance Apprentice including an associate... ...range for this position is $75,000.00 - $165,000.00. The... ..., AM - Portland, AM - Remote Work (US), AM - Sacramento,...Remote workFull timeContract workTemporary workApprenticeshipWork at officeLocal areaVisa sponsorship- ...tailored, all-inclusive insurance solutions for luxury... ...are a team of seasoned underwriting and claim... ...seeking an Underwriting Specialist to join their team. This... ...broker organizations Evaluate the performance of assigned... ...empathetically at all times #LI-Remote Qualifications...Remote workFull timeWork at office
- # Senior Underwriter, Middle Market Multi-IndustryPlano, Texas, United StatesID... ...from leadership. You will evaluate and price moderately complex... ...brokers and agents, so remote hires outside the designated... ...portfolio of brokers, agents, and insureds:* Maintain and grow...Remote workSeniorLocal areaFlexible hours
$100k - $150k
...exciting opportunity for a Senior Underwriter, where a strong, collaborative... ....5-7 years of commercial insurance experienceAdvanced knowledge... ...Work Location:This role may be remote or hybrid, depending on the... ...Employees will accrue 0.0846 hours of Paid Time Off (PTO) per...Remote workSeniorHourly payFull timeTemporary workCasual workLocal areaFlexible hours$75 per hour
...Position: Sociology Teachers, Postsecondary Type: Hourly contract Compensation: $45–$75/hour Location: Remote Commitment: 10–40 hours/week Role... ...training initiatives for postsecondary education. Evaluate and review AI-generated coursework, assignments,...Remote workHourly payContract work- ## Senior UnderwriterApply: Remote Office - US: Full time: Posted Yesterday: R-232... ...Opportunity## Role TitleSenior Underwriter## Purpose of roleThe Senior... ...for underwriting life insurance application using... ...underwriting principles by evaluating health, financial, lifestyle...Remote workSeniorFull timeWork at office
$130k - $160k
Our client, a top-rated insurance carrier, is expanding their underwriting department and seeking to add a Senior Field Commercial Casualty Production... ...territory. This is a fully remote position with a company... .... Develop, analyze, and evaluate information to identify exposures...Remote jobSeniorFlexible hours$120k - $170k
...we are At Intact Insurance Specialty Solutions,... ...an opportunity for an Underwriting Specialist to join our growing Renewable... ...or located remotely. The Underwriting Specialist... ...~ Proven ability to evaluate technical and complex... ...matters more than hours in the office. We are...Remote jobFull timeWork at officeFlexible hours$47.84k - $75k
...hybrid, or (3) fully remote. Hybrid roles are... ...solutions. A Consumer Underwriter – Auto Finance evaluates, negotiates, and decisions... ...schedule; evening hours, limited travel, and... ...flexible health and insurance options including... ...Range $47,840.00 - $75,000.00 An...Remote workFull timeContract workTemporary workPart timeWork experience placementWork at officeRelocation packageFlexible hoursWeekend workAfternoon shift$81k - $138k
...build the future of pharmacy with us. Job Posting Title Senior Underwriter - Remote Job Description The Senior Underwriter is... ...key business owners within Prime. Responsibilities Evaluates the utilization and financial experience of customers and...Remote workSeniorFull timeWork experience placementLocal areaVisa sponsorshipWork visa- ...Description Title: Senior Account... ...Work Mode: Remote/ Eastern and Central... ...during working hours. To view our branch... ..., summaries of insurance, loss runs,... ...research, gather underwriting information,... ...prepare submissions, evaluate and negotiate... ...position is 55-75K annually,...Remote workSeniorContract work
$100k - $150k
...exciting opportunity for a Senior Underwriter, where a strong, collaborative... ...~5-7 years of commercial insurance experience ~ Advanced knowledge... ...: ~ This role may be remote or hybrid, depending on the... ...Employees will accrue 0.0846 hours of Paid Time Off (PTO) per paid...Remote workSeniorHourly payTemporary workCasual workLocal areaFlexible hours- ...Job Description Job Description Underwriter/Senior Processor Job Description: The Underwriter... ...expectations. Work additional hours as needed. Assume responsibility and... ...position based in our Allentown location. Remote work is not available for this role....Remote workSeniorFull timeWork at office
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