Independent Contractor Side Gig Jobs in Springfield, MA

Crum & Forster (C&F), with a proud history dating to 1822, provides specialty and standard commercial lines insurance products through our admitted and surplus lines insurance companies. C&F enjoys a financial strength rating of "A+" (Superior) by AM Best and is proud of our superior customer service platform. Our claims and risk engineering services are recognized as among the best in the industry.

Our most valuable asset is our people: more than 2000 employees in locations throughout the United States. The company is increasingly winning recognition as a great place to work, earning several workplace and wellness awards, including the 2025 Great Place to Work® Award for our employee-first focus and our steadfast commitment to diversity, equity and Inclusion.

C&F is part of Fairfax Financial Holdings, a global, billion dollar organization.  For more information about Crum & Forster, please visit our website: www.cfins.com.

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.

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.

Within the A&H Specialty Business Unit, the Occupational Risk Profit Center focusses on the writing of: Occupational Accident, Contingent Liability and Employers Liability, Non-Trucking Liability, and Physical Damage for Independent Contractors with ancillary Workers’ Compensation for employees. The target markets are the trucking industry and the Gig Economy.

The Operations Assistant is an entry level position supporting the Occupational Risk team. This position will be responsible for supporting the underwriting team through the post binding process, entering data entry into our internal and external systems, completing tax filings and communicating with Brokers/Clients. 

This position is responsible for performing a variety of tasks supporting the accounting and operations functions of the business.  In addition, this individual will support the implementation of new and renewal business for the team while remaining aligned with strategy, commitments and goals of the organization.

This is a hybrid role based in the greater Hartford/Glastonbury, CT area.  If you have insurance experience or new to insurance, this is a great opportunity to come work for a Great Place to Work company.

What you will do for C&F:

• Support underwriting with post-binding procedures and pre-renewal account setup
• Data entry into agency management systems, workflow system, and claims system
• Complete monthly accuracy audit of TPA systems and document verification
• Assist Underwriting team in submission setup
• Assist clients with account administration
• Perform projects and assignments under manager’s direction
• Keep the Operations Shared Drive organized
• Conduct binding documentation accuracy reviews (peer reviews)
• Process document accuracy checks within admin systems (SASID, CBA & ICI)
• Assemble, with accuracy, physical New/Renewal Account folders
• Process Surplus Lines Filings
• Work and communicate effectively with internal and external personnel

What you will bring to C&F:

• High school diploma required
• Bachelor’s degree from an accredited institution preferred
• Intermediate experience with Microsoft Office, specifically Excel, Word, Outlook. Database management experience a plus
• Strong interpersonal and communication (oral and written) skills
• Strong demonstration of problem solving and analytical skills
• A customer focused mentality
• Strong analytical skills
• High degree of organization to prioritize work and follow up on issues
• Will abide by departmental policies and procedures, including authority levels to comply with C&F's risk management controls.
• Exceptional attention to detail
• Other duties as assigned

• 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 owning your career development, so we provide a wealth of ways for you to keep learning, including 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

 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 $37,900.00 to a maximum of $55,600.00. 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.

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