Westfield Health

Underwriter

• Works to acquire the knowledge, experience, skills, and business acumen in the assigned area, which helps in the trainee's development towards the goal of becoming a professional in the respective department.
• Assists leader, team, or business unit with work assigned to them.
• This often includes, but is not limited to, project work and coverage of day-to-day activities.
• Develops business acumen through interactions and shadowing with other professionals.
• Attends business unit meetings, executes research, and creates and delivers presentations as assigned.
• Prepares for and engages in one-on-one, on-line, and on-the-job learning/educational assignments/ experiences.
• Develops operating knowledge of Company standardized hardware, software programs, third-party software, and processing procedures.
• Works toward developing an understanding of key concepts and appropriate business skill application through learning programs, structured on the job experiences, and active participation and engagement in all team building, observation and practice activities.
• Solicits reinforcing and constructive feedback from leader, peer coaches and others in the organization and incorporates feedback into development.
• Identifies resources, best practices, and external networking opportunities to monitor pertinent industry activity and trends.
• Maintains awareness, understanding, and compliance with internal policies and procedures, laws, and regulations appropriate for this position.

Agribusiness Underwriting Trainee

Risk

• Architect, implement, and mature the enterprise risk management framework aligned to strategy, capital, and performance objectives.
• Define and operationalize enterprise risk appetite and tolerances in collaboration with executive leadership and the Board; cascade into policies, incentives, performance management, and investment decisions.
• Establish and maintain enterprise‑wide risk governance, including a common risk language, taxonomy, and measurement standards.
• Develop an effective Three Lines of Defense model, delineating ownership and influence across risk‑related functions including capital management, operational risk, IT/Cyber, compliance, legal, internal audit, and business units.
• Lead recurring Enterprise Risk Assessments (ERAs) and materiality analyses; maintain an enterprise risk register capturing risk velocity, interdependencies, concentrations, and residual exposure.
• Implement key risk indicators (KRIs), early‑warning mechanisms, scenario analysis, stress testing, and emerging risk monitoring.
• Serve as an independent enterprise challenger to strategic decisions, capital deployment, and portfolio trade‑offs.
• Embed risk‑adjusted decision‑making into strategy development, M&A, capital planning, portfolio management, and large‑scale transformation initiatives.
• Partner with the Financial Planning & Analysis (FP&A) department and business leadership to integrate risk impacts into forecasts, plans, and resource allocation decisions.
• Ensure major programs and initiatives include defined risk gates, mitigation plans, and post‑implementation reviews.
• Oversee and strengthen operational risk management, including Risk and Control Self-Assessments (RCSAs), incident and loss event reporting, remediation tracking, and thematic analysis.
• Support enterprise resilience through Business Continuity, Disaster Recovery, and Crisis Management planning, simulations, and after‑action reviews.
• Enhance Third‑Party Risk Management, including due diligence, segmentation, ongoing monitoring, and exit planning using a tiered oversight approach.
• Develop enterprise risk data, analytics, and dashboards to provide timely insights, trend analysis, heatmaps, KRIs, and scenario outcomes.
• Establish effective executive and Board risk reporting cadences and automate reporting processes to improve timeliness and data quality.
• Provide input into ORSA, capital adequacy, emerging risk disclosures, and regulatory risk reporting as applicable.
• Build and sustain a strong enterprise risk culture through clear accountability, role‑based enablement, and leadership engagement.
• Lead, develop, and scale a high‑performing ERM team, including leveraging centers of excellence and embedded business risk champions.
• Provide strategic input to the CRO on segment strategies, risk appetite breaches, and aggregated enterprise risk and capital usage.

Head of Enterprise Risk Management

Accountant

• Prepare and post journal entries to record assumed and ceded reinsurance transactions for multiple treaties.
• Prepare internal reinsurance reports and provide insights and analysis to management.
• Reconcile various balance sheet accounts for reinsurance loss reserves, funds held, and amounts due to and from reinsurers.
• Prepare certain yellow book schedules, such as Schedule F.
• Assist with regulatory reporting and other miscellaneous tasks.
• Prepares and analyzes financial reports to support decision-making processes and identify areas for improvement.
• Ensures compliance with accounting standards and regulations by implementing and monitoring internal controls and policies.
• Develops and maintains relationships with stakeholders such as auditors, regulators, and other departments to facilitate effective communication and collaboration.
• Manages financial risks by assessing and mitigating risks related to investments, claims, and other financial activities.
• Develops and monitors budgets and forecasts to ensure financial stability and growth of the company.
• Conducts financial analysis and provides insights to management on financial performance, trends, and opportunities.
• Prepares monthly property/casualty and non-insurance financial statements and supplemental reports on both a Statutory and a GAAP basis.
• Leads frequent communication with external customers, including state and federal regulators and auditors, and internal business partners at all levels in the organization, on topics such as responding to their specific questions on regulatory filings, the process used to calculate a journal entry, or questions on what specific expenses are captured in a certain line on a regional income statement.
• Supports audits by providing necessary documentation, data, and information to internal and external auditors to ensure compliance and accuracy.
• Works with business leaders and others within the Finance department to ensure that correct structures (tree based) are in place for accurate reporting within the accounting system.

Reinsurance Accountant

Backend Engineer

• Build Python services & SDKs that expose LLM/agent capabilities to internal teams; operate them on Kubernetes/OpenShift.
• Support agent runtimes & workflows by implementing and managing operational workflows around AI technologies (e.g. LangGraph, OpenAI Agent SDK, MCP, others).
• Develop a cohesive enterprise platform for GenAI use cases that run the gamut from core insurance workflows to back office assistants.
• Own platform reliability, scalability, performance, and cost.
• Observability: add tracing/metrics/logging via our enterprise tools and monitoring infrastructure to create actionable dashboards/alerts.
• Security & governance: keep linters and code scan reports clean; enforce RBAC, audit trails, data-access policies, PII controls, and prompt-injection defenses.
• CI/CD at scale: help own Azure DevOps YAML pipelines (pipeline-as-code) to enable deploy on demand; use feature flags and other techniques for release on demand.
• Testing culture: drive a culture of fast unit tests, contract tests, and performance tests; keep coverage meaningful and PR checks green.
• Dependency & packaging hygiene: manage Python envs and builds with uv and containerization.
• Docs & enablement: produce runbooks, reference implementations, and developer guides; mentor teams on how to use the platform.

Senior Python Engineer – GenAI Platform

Executive Assistant

• Manage multiple complex and dynamic calendars, resolving conflicts and anticipating scheduling needs
• Coordinate domestic and international travel arrangements, including itineraries, logistics, and expense documentation
• Serve as a primary point of contact for internal and external communications on behalf of senior leaders
• Prepare presentations, briefing materials, and other executive-level documents with accuracy and professionalism
• Support financial and business unit meetings by coordinating agendas, logistics, materials, and follow-up actions
• Prepare, submit, and track expense reports in a timely and accurate manner
• Track key initiatives, deadlines, and deliverables across teams, ensuring alignment and follow-through
• Proactively anticipate issues, assess risks, and recommend solutions to support leadership effectiveness
• Handle highly confidential and sensitive information with discretion, integrity, and sound judgment
• Build strong, collaborative relationships with leaders, team members, and external partners
• Screen and respond to incoming calls, requests, and visitors, prioritizing appropriately
• Perform additional duties and responsibilities as assigned

Human Resources

• Serve as the first point of contact for employees, former employees, and managers with questions related to HR policies, procedures, systems, and programs.
• Respond to employee inquiries through the HR Help Desk case management system in Oracle, ensuring timely, accurate, and customer‑focused resolution.
• Process HR transactions such as new hires, rehires, job changes, promotions, transfers, compensation changes, terminations, and personal data updates.
• Support onboarding activities, including new hire documentation and facilitation of new employee orientation
• Partner with employees and third-party vendors to coordinate leaves of absence
• Maintain employee records and personnel files in compliance with confidentiality and data security requirements.
• Support compliance activities, including, I‑9 processing, labor law posters, background checks, and audits.
• Leverage HR reports (e.g., headcount, turnover, trends) to support HR leadership and operational decisions.
• Identify opportunities to improve HR processes and contribute to projects and initiatives that enhance efficiency and the employee experience.
• Collaborate with HR team members to ensure consistent service delivery and successful outcomes.

HR Operations Professional

Vice President

• Spearhead client engagement to bolster profitable growth within key client segments, ensuring exceptional "client experience" through strategic planning, thought leadership, and relationship management.
• Lead the effort to raise corporate profile, effectiveness, and reputation by deepening and extending our agency/brokerage relationships:
• Support the overall strategic management of the key broker relationships.
• Developed under-served territories.
• Identify and qualify new broker relationships.
• Cultivate and sustain relationships with primary stakeholders within our top-tier accounts and their distribution allies.
• Drive key business development strategies (broker diversification, account targeting and cross-sell) in conjunction with our brokerage partners that maximize revenue opportunities across a wide territory.
• Actively manage meeting calendars, agendas and follow ups with our key agency partners.
• Interact and develop relationships with each key broker's "relationship manager."
• Design and implement client engagement strategies in tandem with profit center leaders.
• Facilitate client-centric advisory sessions, in partnership with profit center leadership and marketing teams.
• Exhibit a thorough understanding of the Specialty commercial marketplace by staying well-informed about offerings, services, market positioning, and unique selling points.
• Collaborate with data analysts to pinpoint growth indicators, creating and enhancing data / tools to track progress and drive cross selling

Senior Vice President, Distribution

DevOps Engineer

• Lead the implementation and continuous improvement of our DevOps toolchain, focusing on automation, scalability, and security integration.
• Work directly with development teams to promote DevOps principles, optimizing workflows, enabling shift-left practices, and reducing friction in day-to-day engineering.
• Design, build, and maintain CI/CD pipelines using infrastructure-as-code and pipeline-as-code. (e.g. Azure DevOps, Kubernetes YAML, and Terraform)
• Help manage and scale containerized workloads on Kubernetes/OpenShift clusters.
• Integrate quality and security checks into the development lifecycle using tools like SonarQube, Snyk, etc.
• Explore, evaluate and implement advancements to our DevOps practice. (e.g. New cloud deployment patterns, internal developer platform, GenAI development practices and safeguards)
• Provide thought leadership in advancing the organization’s DevOps strategy, alignment with business goals and technology trends.
• Advance branching and code merge strategies that enable frequent,
• Streamline the development and deployment platforms and processes, ensuring efficient collaboration between development, infrastructure and other stakeholders.
• Ensure synergies between software development and IT operations through automation, Continuous Integration / Continuous Deployment (CI/CD) pipelines and infrastructure management standards and best practices.

Senior DevOps Engineer

SDET

• Design, develop, and maintain robust automated test frameworks for API, UI, integration, performance, and end-to-end testing.
• Write production-level automation code using modern languages (e.g., Java, Python, JavaScript/TypeScript, C#).
• Implement shift-left engineering by partnering with developers on unit testing patterns, code quality, and testability design.
• Ensure automated tests integrate into CI/CD pipelines to improve feedback speed and delivery confidence.
• Identify and automate high-value opportunities that replace manual or repetitive validation.
• Use GenAI tools for test generation, code suggestions, defect classification, and quality insights.
• Contribute to self-healing automation frameworks and AI-assisted testing accelerators.
• Promote responsible use of AI for engineering workflows and coach team members in AI-supported testing techniques.
• Translate business and system requirements into risk-based testing strategies and automation coverage models.
• Partner with developers, architects, and QE Leads to design API-first quality strategies aligned to platform modernization.
• Contribute to test data design, service mocks, simulation layers, and synthetic test environments.
• Analyze logs, telemetry, and monitoring data to identify systemic issues and drive long-term quality improvements.
• Work directly with Application Engineering, DevSecOps, Architecture, and Operations to build a unified quality model.
• Improve pipeline quality through CI/CD best practices, static analysis, quality gates, and automated checks.
• Participate in production issue reviews; identify root causes and inject corrective actions into future sprints.
• Mentor junior engineers and testers on automation patterns, debugging, API testing, and engineering best practices.
• Perform hands-on testing of complex workflows, integrations, and edge cases where human judgment is required.
• Evaluate defects, logs, and system behavior to identify gaps in coverage or test strategy.
• Maintain high-quality documentation for test frameworks, automation suites, and quality processes.
• Evaluate and recommend new tools, frameworks, and engineering techniques aligned with enterprise standards.

Senior Software Development Engineer, Test (SDET)

Claims Specialist

• Review photos, reports, and other documentation from the inspection, to assess damage and prepare accurate estimates.
• Utilize industry-standard estimating platform Xactimate, to produce detailed repair scopes.
• Determine appropriate repair vs. replacement decisions based on best practices, jurisdictional code requirements, and policy coverage.
• Validate the accuracy of insured and/or contractor submitted estimates and to negotiate discrepancies when necessary.
• Apply current industry repair standards, materials pricing, labor rates, and construction methodologies.
• Provide technical expertise to frontline claims staff.
• Communicate clearly with customers, contractors, and vendors to explain scope and estimate decisions as/is necessary.
• Document all file activity in accordance with company and regulatory requirements.
• Support supplemental estimate reviews.
• Ensure all estimates comply with company guidelines, state regulations, and industry’s best practices.
• Maintain high levels of accuracy, productivity, and cycle time performance.
• Provides support in negotiation of settlements with insureds, attorneys, and other insurance companies.
• Manages approved vendors and counsel utilized as necessary in the claim process, including approval of investigation plans and budgets.
• Monitors, reviews, and issues payments to vendors and counsel in accordance with guidelines and standards.
• Establishes proper reserves for each claim based upon thorough investigation, evaluation, and experience.
• Refers claims exceeding authority to appropriate manager or complex claims specialist with recommendations.
• Meets established goals & objectives, arranges for salvage disposition and other recovery proceedings as necessary, participates in claim file reviews and audits with customer and broker.
• Formulates sound recommendations for claims file handling, subsequent transactions, and renewal processing.
• Contribute to continuous improvement efforts, guideline updates, and internal training initiatives.

Senior Claims Representative – Estimator

Account Manager

• Handles underwriting information, new business and renewal set up, processing, projects, and/or communication assignments for Commercial Lines.
• Sets up new business and/or renewal business applications for quoting, coordinates timely turnaround with underwriter, and reviews quote for accuracy.
• Supports the underwriting function at Westfield, gathers outstanding information from producers and customers and manages issue instructions when an order is received from the producers/customer.
• Assists review of individual accounts learning exposure identification and acceptability of risk in accordance with company guidelines and standards.
• Determines acceptability of risk in accordance with company guidelines and standards by reviewing the application and risk for exposure identification.
• Notifies agencies or producers of adverse underwriting decisions, underwriting requirements, status, and declinations.
• Answers questions for agencies and producers, policyholders and other external contacts.
• Ensures customer service excellence with internal business partners using Service Level Agreements (SLAs), metrics, and ongoing feedback regarding timeliness, quality, and quantity of completed work.
• Supports the analysis, takes decisions on, and processes new business applications, endorsements, and renewals for multiple lines of insurance.
• Delivers policy retention, premium adequacy, and customer-focused quality of new and in force business.
• Evaluates and updates policy information that support premium generation, policy review, and assembly.
• Updates partner quote, coverage review, error corrections, risk factors, correct classification, and premium growth opportunities.
• Orders and analyzes investigative reports and predictive Underwriting on present or potential customers.
• Reviews and acts on estimates of coverage gaps, statements of value, and other key underwriting information.
• Develops underwriting acumen, reviews system submitted requests, inquiries received by email and phone to identify type of risk and if underwriting referral is necessary.
• Develops relationships with key producers, agency personnel, other distribution partners, and customers.
• Maintains and strengthens the established relationship with the agency personnel, producers, other distribution partners, local and home office team members, and the customer.
• Collaborates with other Westfield teams such as Customer Care Center, Mail Center, and Claims to accomplish department service, quality, and profitability goals and assists the Legal department with reviews and responses.

Commercial Lines Support Account Representative

• Works on a project or projects that align with and contribute to accomplishing the Human Resources team objectives.
• Completes assigned tasks and projects efficiently and effectively, following instructions and guidelines provided by supervisors or mentors.
• Conducts research, gathers data, and analyzes information relevant to the internship focus or assigned projects.
• Identifies and resolves issues or challenges that arise during the internship, demonstrating problem-solving skills and a proactive approach to finding solutions.
• Collaborates with colleagues, supervisors, and other stakeholders to effectively communicate progress, challenges, and ideas.
• Participates in on the job learning, workshops, networking, and training programs, to enhance knowledge and skills related to the field or industry of the internship.

Human Resources Intern, Summer 2026

QA Engineer

• Leads and matures quality engineering practices using modern agile, DevSecOps, and continuous testing methodologies.
• Defines a future‑ready vision for how development and testing intersect, ensuring shared ownership of quality across SDETs, developers, and engineering teams.
• Partners with Application Engineering Managers to embed testability, automation, and quality metrics into the software design and development lifecycle.
• Builds and coaches a highly technical team of SDETs, QE Leads, and quality engineers focused on scalable and maintainable automation solutions.
• Designs and executes enterprise‑aligned automation strategies emphasizing long‑term maintainability, shift‑left/shift‑right practices, and engineering‑driven quality.
• Integrates AI‑driven testing capabilities such as autonomous test generation, self‑healing frameworks, and machine‑learning‑based insights to increase efficiency and coverage.
• Collaborates with Product Owners, Engineering Managers, and QE Leads to optimize test coverage, ensuring critical workflows remain thoroughly validated.
• Defines and monitors key quality KPIs, including defect leakage rate, automation ROI, coverage metrics, and pipeline stability.
• Establishes a cohesive strategy for unit, integration, API, regression, and exploratory testing—co‑owned with development leaders.
• Ensures regression strategies adapt to release scope, defect trends, and product risk profiles.
• Partners with Application Engineering, DevSecOps, Operations, and Architecture leadership to build a unified, modern engineering model.
• Drives quality‑in‑pipeline capabilities across CI/CD, Release‑on‑Demand, and cloud‑based delivery environments.
• Leads cross‑team investigations of production issues, ensuring systemic quality improvements are built into future iterations.
• Evaluates next‑generation quality tooling, cloud‑based testing platforms, and AI‑centric testing accelerators for adoption.
• Manages vendor relationships, contract negotiations, and tool procurement for the quality engineering ecosystem.
• Ensures compliance with enterprise security, data privacy, and regulatory requirements across all QE processes.
• Builds a high‑performing, engineering‑centric QE organization through hiring, career development, succession planning, and ongoing coaching.
• Fosters a culture of continuous learning, innovation, and experimentation, encouraging the adoption of emerging tools and modern engineering practices.
• Removes organizational and technical obstacles to ensure the efficient delivery of high‑quality releases.
• Manages budgets for QE tooling and staffing.
• Identifies opportunities for cost optimization without compromising software quality or delivery efficiency.

IT Quality Engineering Manager

• Review and analyze incoming transactions and related information for completeness accuracy and quality.
• Excess Casualty new business submissions, renewal submissions and endorsements processing including rating, policy construction and assembly in a timely and accurate manner.
• Regularly reviews and adheres to department processing guidelines and procedures to ensure accuracy including recommended changes/enhancements.
• Manage underwriting relationships with timely responses relative to service inquiries.
• Maintain all correspondence activity with internal and external customers including daily diaries on pending transactions.
• Compliance with state rules and regulations relative to cancellations and reinstatements.
• Gathering and analyze underwriting information including experience reports, final audits, loss control reports, financial reports, loss runs, MVRs, and FEINs.
• Ability to manage internal report updates based on manager discretion.
• Participates in peer review and quality control for team(s) as needed.
• Special projects, including participation of Home Office projects, as needed.

Specialty Underwriting Assistant

Growth Marketing

• Own and execute demand generation programs that drive pipeline, activation, and revenue.
• Design and run experiments across paid, lifecycle, and sales-assisted channels to support near-term growth.
• Partner closely with the CEO and sales to design and run experiments that drive customer acquisition and activation across PLG and founder-led sales channels.
• Own the self-serve sign-up and onboarding funnel, running experiments to improve activation, time-to-value, and trial-to-paid conversion.
• Interview customers and prospects to understand workflows, objections, and language – and turn insights into messaging and campaigns.
• Run experiments tied directly to pipeline, conversion, and revenue impact.
• Set up and maintain a lightweight but reliable growth stack (Webflow, HubSpot, analytics) to track the funnel and guide decisions.
• Test and scale a focused mix of paid channels (Google, Meta, LinkedIn) once messaging and ICP are validated, using freelancers or agencies where it adds leverage.
• Define and refine ICPs and buying journeys across self-serve and sales-assisted paths to keep marketing, product, and sales aligned.
• Use product usage and CRM data to identify high-intent signals and trigger lifecycle campaigns that drive expansion, referrals, and upsell.
• Plan and produce organic content: social posts, articles, newsletters –that educates and drives engagement, especially on LinkedIn.
• Partner with industry associations to co-create content, host webinars, and activate member networks.
• Analyze pipeline, conversion, CAC, and revenue performance.
• Contribute to our content engine with playbooks, customer stories, how-tos, and practical resources.
• Use AI tools to streamline content creation and marketing automation.