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Remote Captive Insurance Jobs in Connecticut (NOW HIRING)

Regional Sales Manager

West Hartford, CT · Remote

$150K - $500K/yr

... insurers in the United States. #LI-ND1 #LI-Remote The company is an equal employment opportunity employer. Responsibilities As a Regional Sales Manager, you'll develop medical stop loss/captive ...

Regional Sales Manager

West Hartford, CT · Remote

$150K - $500K/yr

... insurers in the United States. #LI-ND1 #LI-Remote The company is an equal employment opportunity employer. As a Regional Sales Manager, you'll develop medical stop loss/captive program projects and ...

Remote Captive Insurance information

What are the key skills and qualifications needed to thrive as a remote captive insurance professional?

To thrive as a Remote Captive Insurance Professional, you need a deep understanding of insurance principles, risk management, and compliance, often supported by a degree in finance, business, or insurance and relevant industry certifications. Familiarity with captive insurance management software, regulatory compliance systems, and data analysis tools is typically required. Strong analytical thinking, attention to detail, and effective communication are essential soft skills for building client relationships and managing complex insurance structures remotely. These skills ensure regulatory adherence, optimal risk solutions, and successful client outcomes in a specialized and evolving insurance sector.

What is the difference between Remote Captive Insurance vs Remote Insurance Underwriter?

AspectRemote Captive InsuranceRemote Insurance Underwriter
CredentialsInsurance licenses, actuarial or risk management certificationsInsurance licenses, underwriting certifications
Work EnvironmentCorporate or consulting firms, remote options commonInsurance companies, remote or office-based roles
Industry UsageSpecializes in creating and managing captive insurance companiesEvaluates and prices insurance risks for clients

Remote Captive Insurance professionals focus on establishing and managing captive insurance entities, often requiring risk management expertise and industry-specific licenses. Remote Insurance Underwriters assess risks and determine policy terms, also needing insurance credentials. While both roles operate remotely and within the insurance industry, their core functions differ: one manages captive entities, the other underwrites policies.

What are some common challenges faced by professionals working in remote captive insurance roles?

Professionals in remote captive insurance positions often encounter challenges related to communication and collaboration, as much of the work involves coordinating with underwriters, actuaries, and clients across different locations and time zones. Staying updated on regulatory changes and maintaining compliance can also be demanding, given the highly specialized and evolving nature of captive insurance. Additionally, remote roles require strong self-discipline and proactive time management to meet deadlines and ensure high-quality service without in-person supervision.

What is a remote captive insurance professional?

A Remote Captive Insurance professional is someone who manages or administers captive insurance companies while working remotely, typically from home or any location outside a traditional office. Captive insurance refers to an insurance company created by a parent company to insure its own risks. These professionals handle tasks such as compliance, underwriting, claims processing, and reporting via digital communication tools. The remote aspect allows for flexibility and often requires strong self-management and technological skills. Remote captive insurance roles are increasingly common as the insurance industry adapts to more flexible work arrangements.

What are the most commonly searched types of Captive Insurance jobs in Connecticut?

The most popular types of Captive Insurance jobs in Connecticut are:

What cities in Connecticut are hiring for Remote Captive Insurance jobs?

Cities in Connecticut with the most Remote Captive Insurance job openings:

Infographic showing various Remote Captive Insurance job openings in Connecticut as of August 2026, with employment types broken down into 88% Full Time, 6% Part Time, and 6% Contract. Highlights an 100% Remote job distribution.

Sr./Lead Accountant, Reinsurance (Remote or Glastonbury, CT/Hybrid)

Crum & Forster

Glastonbury, CT • On-site, Remote

$1.3K/mo

Full-time

Medical, Dental, Vision, Retirement, PTO

Re-posted 10 days ago


Job description

Crum & Forster Company Overview

Crum & Forster (C&F) provides market leading property & casualty, accident & health, specialty and standard commercial lines insurance solutions. A true underwriting company, we have a 200-year history of helping our customers manage risk with laser-focused expertise, integrity and discipline. Our people are empowered to make decisions and problem-solve with you smartly and swiftly. Our annual gross written premium is 6.2 billion. C&F enjoys a financial strength rating of "A+" (Superior) by AM Best.

Our most valuable asset is our people. We have 3000 employees, and locations throughout the United States and India. With our employee-first focus, the Company is consistently recognized as a great place to work, earning multiple workplace and wellness awards, including the Great Place to Work Award, Fortune 100 Best Companies to Work For, Fortune Best Workplaces for Parents, Fortune Best Workplaces for Millennials, and many others.

C&F is part of Fairfax Financial Holdings. For more information about C&F, please visit our website: www.cfins.com

Job Description

Since 2000, Crum & Forster's Accident & Health division (A&H) has offered a diverse portfolio of specialty insurance and reinsurance products nationwide. We place a strong focus on product development and creative distribution methods, along with excellent client service and support.

In addition to our robust domestic portfolio, which spans both special risk and medical solutions, A&H works on an international basis through various partnerships. Our global capabilities provide our partners with even broader flexibility in underwriting solutions.

The qualities and capabilities of Crum & Forster Accident & Health demonstrate our philosophy of building meaningful, long-term partnerships and our dedication to providing alternative strategies in an ever-changing insurance market.

 

The A&H Specialty Business Unit takes a forward-thinking, flexible approach to solutions that span a robust slate of products tailored to needs in Special Risk, International Travel Medical, retail and wholesale Travel and Occupational Risk. At year-end 2024, the SBU recorded $1,391M in gross premium written.

 

Information about the Role, Line of Business and Team:

As the Occupational Risk Profit Center continues to grow, so does the need for talented individuals to aid in the success of the division.   This role will focus on the accounting and finance responsibilities associated with managing an Insurance Agency within an Insurance Carrier. In this position you will interact internally with: Underwriting, Actuarial, Claims, Compliance, IT, and externally with Occupational Accident's business partners.

  • The role can be based on our Glastonbury, CT location/hybrid or Remote. If remote, quarterly travel and additional travel as needed is required to our Glastonbury, CT location.

What you will do:

  • Oversee and manage all accounting functions related to occupational accident operations, ensuring compliance with industry regulations, GAAP, and internal policies.
  • Prepare, analyze, and oversee monthly, quarterly, and annual financial statements, including balance sheets, income statements, and cash flow statements.
  • Manage the month-end, quarter-end, and year-end close processes, including journal entries, reconciliations, and reporting, ensuring all deadlines are met.
  • Conduct detailed account reconciliations and address discrepancies to ensure accuracy and compliance.
  • Prepare monthly general ledger interface entries to record premiums, expenses, losses, and commissions.
  • Analyze financial data and provide insights to support decision-making, strategic planning, and forecasting.
  • Support the preparation of budgets and forecasts by providing detailed financial analysis and variance explanations.
  • Oversee the receiving, invoicing, vendor payment, and commission payment processes, resolving discrepancies as needed.
  • Guide and mentor junior accounting staff, fostering a collaborative and productive work environment, and assist with training new team members.
  • Collaborate with internal and external auditors during audits, providing necessary documentation and explanations.
  • Review, improve, and implement process changes to yield greater efficiencies within accounting operations.
  • Utilize Salesforce and Accounting Seed to manage accounting data, track performance metrics, and generate reports for management review.
  • Process and review intercompany billing and transactions, ensuring proper documentation and accuracy.
  • Assist in reviewing and documenting business processes to identify opportunities for improvement and support implementation projects, including new accounting systems or software.
  • Stay current on industry trends and best practices to enhance the effectiveness of accounting operations.

Captive and Reinsurance-Specific Functions:

  • Oversee and manage accounting for captive insurance entities, including preparation of statutory financial statements and regulatory filings.
  • Coordinate and reconcile reinsurance transactions, including ceded and assumed premiums, losses, and commissions.
  • Prepare and analyze Schedule F (Reinsurance) and other regulatory schedules related to reinsurance and captive operations.
  • Monitor and account for collateral and trust arrangements associated with captive and reinsurance agreements.
  • Ensure compliance with all regulatory requirements specific to captives and reinsurance, including reporting to state insurance departments.
  • Liaise with captive managers, reinsurers, and external auditors to support audits and regulatory examinations.
  • Assist in the structuring and accounting for new captive and reinsurance programs, including documentation and implementation of related processes.

What YOU will bring to C&F:

  • Strong technical and analytical skills with a focus on data driven workflows.
  • Ability to work in a fast paced, deadline-driven environment, independently, and collaborate with a team.
  • Strong written and verbal communication skills
  • Ability to facilitate team conflict resolution.
  • Communicates information in a clear, concise, and timely manner using appropriate channels of communication.
  • Strong organization and time management skills with exceptional attention to detail

Requirements:

  • Bachelor's degree in Accounting, required. *Will accept other business field Majors only with Captive/Reinsurance experience present.
  • Property & Casualty (P&C) line experience is a plus.
  • Captive/Reinsurance experience preferred.
  • Minimum of 5 years of professional accounting experience, within the insurance industry.
  • Intermediate experience with Excel, Word, Outlook, Access, and database management; Tableau experience is a plus.
  • Strong emphasis on advanced Excel knowledge, including formulas, pivot tables, and data analysis.

#LI-MS

#LI-REMOTE

What C&F will bring to you
  • Competitive compensation package
  • Generous 401K employer match
  • Employee Stock Purchase plan with employer matching
  • Generous Paid Time Off
  • Excellent benefits that go beyond health, dental & vision. Our programs are focused on your whole family's wellness, including your physical, mental and financial wellbeing
  • A core C&F tenet is supporting your career development, so we provide a wealth of ways for you to keep learning, which may include tuition reimbursement, industry-related certifications and professional training to keep you progressing on your chosen path
  • A dynamic, ambitious, fun and exciting work environment
  • We believe you do well by doing good and want to encourage a spirit of social and community responsibility, matching donation program, volunteer opportunities, and an employee-driven corporate giving program that lets you participate and support your community

At C&F you will BELONG

If you require special accommodations, please let us know. We value inclusivity and diversity. We are committed to equal employment opportunity and welcome everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, or Veteran status. If you require special accommodations, please let us know. Belonging at C&F, is a mindset. It's about fostering a culture of inclusion and connection, where everyone feels valued, heard, and empowered to thrive and where our social impact efforts help strengthen the communities where we live and work.

For California Residents Only:  Information collected and processed as part of your career profile and any job applications you choose to submit are subject to our privacy notices and policies, visit https://www.cfins.com/onlineprivacypolicy/ca/noticeatcollection/  for more information.

Crum & Forster is committed to ensuring a workplace free from discriminatory pay disparities and complying with applicable pay equity laws.  Salary ranges are available for all positions at this location, taking into account roles with a comparable level of responsibility and impact in the relevant labor market and these salary ranges are regularly reviewed and adjusted in accordance with prevailing market conditions. The annualized base pay for the advertised position, located in the specified area, ranges from a minimum of $74,900 to a maximum of $110,000. The actual compensation is determined by various factors, including but not limited to the market pay for the jobs at each level, the responsibilities and skills required for each job, and the employee's contribution (performance) in that role. To be considered within market range, a salary is at or above the minimum of the range. You may also have the opportunity to participate in discretionary equity (stock) based compensation and/or performance-based variable pay programs.

Employment Type: FULL_TIME