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Remote Captive Insurance Manager Jobs in Indiana

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Remote Life Insurance Agent

Gary, IN · Remote

$69K - $150K/yr

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Remote Life Insurance Agent

Gary, IN · Remote

$69K - $150K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Showing results 41-60

Remote Captive Insurance Manager information

What is a remote captive insurance manager?

A Remote Captive Insurance Manager is a professional who oversees the operations and compliance of captive insurance companies while working remotely. Captive insurance companies are subsidiaries created to provide insurance to their parent organization, often for specialized risks. The manager handles regulatory filings, financial reporting, policy issuance, and communication with regulators and service providers—all from a remote location. This role requires expertise in insurance regulations, financial management, and strong communication skills to coordinate with clients and regulatory agencies.

How does a remote captive insurance manager collaborate with on-site teams and external stakeholders to ensure compliance and effective risk management?

A Remote Captive Insurance Manager typically coordinates closely with on-site finance, legal, and risk management teams through regular video conferences, emails, and collaborative project management tools. They frequently interact with external auditors, regulators, and service providers to ensure the captive insurance entity remains compliant with all relevant laws and industry standards. Despite being remote, maintaining strong communication and documentation practices is essential to address challenges such as time zone differences and real-time decision-making. This collaborative approach helps ensure effective risk assessment, timely reporting, and successful management of the captive insurance program.

What are the key skills and qualifications needed to thrive as a remote captive insurance manager, and why are they important?

To thrive as a Remote Captive Insurance Manager, you need a strong background in insurance, risk management, and financial analysis, typically supported by a relevant degree and experience in the captive insurance industry. Familiarity with insurance management software, regulatory compliance systems, and certifications such as ARM or CPCU is often expected. Exceptional organizational skills, self-motivation, and clear communication are vital for effectively managing client relationships and coordinating with remote teams. These skills ensure the compliant, efficient, and strategic operation of captive insurance programs, which is crucial for meeting client needs and regulatory standards.

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

AspectRemote Captive Insurance ManagerRemote Insurance Underwriter
CredentialsInsurance licenses, industry certificationsInsurance licenses, underwriting certifications
Work EnvironmentManagement of captive insurance programs, client interactionAssessment of insurance applications, risk analysis
Employer & IndustryCaptive insurance companies, risk management firmsInsurance carriers, brokerage firms

The Remote Captive Insurance Manager focuses on managing and overseeing captive insurance entities, while the Remote Insurance Underwriter evaluates insurance applications and assesses risks. Both roles require industry licenses and operate within the insurance sector, but their responsibilities and work environments differ significantly.

What cities in Indiana are hiring for Remote Captive Insurance Manager jobs?

Cities in Indiana with the most Remote Captive Insurance Manager job openings:

Infographic showing various Remote Captive Insurance Manager job openings in Indiana as of June 2026, with employment types broken down into 4% As Needed, 29% Full Time, 59% Part Time, 2% Temporary, and 6% Contract. Highlights an 35% Physical, 3% Hybrid, and 62% Remote job distribution.

Account Executive-Indiana Captive Territory

Sentry Insurance

Evansville, IN • On-site, Remote

$82K - $118K/yr

Full-time

Medical, Dental, Vision, Retirement

Re-posted 3 days ago


Sentry Insurance rating

8.7

Company rating: 8.7 out of 10

Based on 46 frontline employees who took The Breakroom Quiz

72nd of 315 rated insurance


Job description

Our highly trained Account Executives present specialized commercial insurance, 401K, and life insurance products that are perfectly designed for the industries we serve.

You’re not just in it to win it. You want to crush it every time. Because that’s what our sales professionals do. Not just anyone has what it takes to build strong and profitable relationships. If you’re a unique performer, Sentry offers a career opportunity that soars beyond commercial insurance sales.

We provide everything you need to carve out a sales career filled with success and purpose, including:

  • High earning potential with base salary, commissions, monthly/annual incentives, plus recognition trips

  • Outstanding benefits and a 401(k)-program matching dollar for dollar up to 8%

  • Opportunities for professional development and growth

  • Outstanding training and support

  • An industry-leading line of products and services

Total currently estimated projected compensation range for this position is $82,551-$118,551, which is a combination of base pay, currently projected renewal commissions, and currently estimated new business commission opportunities. Commission opportunities – both renewal and new business -- are based on achievement of sales objectives and compliance with the terms of the applicable incentive plan.

The Indiana territory includes: the greater Evansville area.  Residence within the sales territory is required.

What You’ll Do

  • Sell directly to niche market accounts to increase premium volume

  • Retain profitable business by providing effective, quality service to policyholders

  • Build and maintain quality relationships with businesses

  • Work directly with Underwriting, Claims, Loss Control, Audit, Customer Service, and other key partners

  • Call on and pursue all niche market opportunities assigned to your geographic territory

  • Leverage current customers and relationships for new growth and sales opportunities 

What it Takes

  • Bachelor’s degree or equivalent work experience/related sales experience

  • The ability to obtain and maintain the necessary P&C, and Life licenses required to sell the products Sentry offers

  • Self-discipline and ability to thrive in a remote work environment

  • Ability to multitask, prioritize, communicate effectively, and remain organized

  • Strong analytical and math skills

  • Acceptable Motor Vehicle Record with a valid driver’s license and ability to meet travel requirements

Here is what you can look forward to as part of our team:

At Sentry, your total rewards go beyond competitive compensation. We’re committed to supporting the whole you, which is why we offer a comprehensive package designed to help you thrive both professionally and personally.

  • Home Office: Enjoy the best of both worlds. With a home office set up and time in the field, with regular travel in your company car in your defined territory. We provide the cutting edge proprietary technology and tools you need to be more efficient and effective in the field including a laptop and cell phone reimbursement.

  • Continuous Learning: Unlock your potential through Sentry University, including comprehensive, ongoing training, including licensure and take advantage of our tuition reimbursement program.

  • Comprehensive Benefits: We support your whole self with group medical, dental, and vision insurance along with parental leave, pet insurance, caregiver leave, and wellness resources. Options for HSA, FSA, and Dependent Care FSA are available.

  • Investing in Your Future: We’re committed to your long-term financial well-being. We offer a 100% company match on the first 8% you contribute to your 401(k) each pay period, and those funds vest immediately.

  • Giving Back: Through the Sentry Foundation, we’re proud to support the United Way and make a difference in our communities.

Why Join Sentry?

At Sentry, we believe our people are the heart of our success. We’re proud to be recognized for the culture we’ve built, earning spots on Forbes’ lists for America’s Best Midsize Employers and Best Employers for New Grads, as well as Newsweek’s America’s Greatest Workplaces for Women and Diversity. These honors reflect our commitment to your professional satisfaction and growth.

Building on a Legacy

Our future is bright, but it’s anchored in a long history of stability. Since our founding in 1904, we’ve dedicated ourselves to helping businesses protect their futures. That trust has made us one of the largest and most financially stable mutual insurance companies in the U.S. We’re proud to have maintained an A+ rating from A.M. Best, the industry’s leading authority, for over 30 years.

Your Career, Our Community

Whether you’re working at our headquarters in Stevens Point, Wisconsin, or one of our many offices across the country, you’ll find a challenging and rewarding environment. Explore the Our Teams tab on our Career Page to see the diverse career paths we offer, with a focus on ongoing development and professional growth.

Ready to own your future? Join us at Sentry, opportunities await!

Casey Van Der Geest

Talent Acquisition Specialist

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.


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