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Captive Jobs in Florida (NOW HIRING)

Crumdale Specialty

Captive Solutions Partner

Orlando, FL

$108K/yr

Crumdale Specialty is seeking a Captive Sales Advisor to partner with Regional Sales Directors to win alternative funding opportunities specifically by turning "captive" from a conceptual idea into a ...

Crumdale Specialty

Captive Solutions Partner

Destin, FL

$105K/yr

Crumdale Specialty is seeking a Captive Sales Advisor to partner with Regional Sales Directors to win alternative funding opportunities specifically by turning "captive" from a conceptual idea into a ...

Everlong Captive Consulting Group

Be Seen First

Vice President, Member Experience

Ponte Vedra, FL · On-site

$120K - $140K/yr

Fuel captive growth by building and maintaining strong client and broker relationships. * Identify and deliver cost-containment innovations that produce measurable, high ROI for clients. * Drive ...

The Hartford

Captives Underwriter

Lake Mary, FL · Hybrid

$124K - $199K/yr

The Captives Underwriter's major purpose is to profitably grow their assigned Captive Programs and achieve underwriting excellence. The Captives Underwriter does not have any direct reports but is ...

The Hartford

Captives Underwriter

Lake Mary, FL · Hybrid

$124K - $199K/yr

The Captives Underwriter's major purpose is to profitably grow their assigned Captive Programs and achieve underwriting excellence. The Captives Underwriter does not have any direct reports but is ...

cokeflorida

Senior Manager, Risk Financing

Tampa, FL · On-site

The role partners closely with Finance, Claims, ERM, the Captive Manager, Legal, operating affiliates, brokers, actuaries, carriers, and reinsurers to ensure risk financing decisions are analytically ...

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Captive information

See Florida salary details

$10

$16

$37

How much do captive jobs pay per hour?

As of Aug 30, 2026, the average hourly pay for captive in Florida is $16.34, according to ZipRecruiter salary data. Most workers in this role earn between $11.68 and $16.15 per hour, depending on experience, location, and employer.

What is a captive in the context of insurance?

Captives are specialized insurance companies that are created and wholly owned by one or more non-insurance companies to insure the risks of their owners. They allow organizations to manage risk more efficiently and potentially reduce insurance costs by retaining profits that would otherwise go to third-party insurers. Captives can provide coverage that may not be available or affordable in traditional insurance markets and offer more control over claims handling and risk management. They are subject to regulations and must be legally established according to the jurisdiction in which they operate.

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

To thrive as a Captive Insurance Manager, you need in-depth knowledge of insurance principles, risk management, and a relevant degree such as finance or accounting. Familiarity with captive management software, regulatory compliance tools, and industry certifications like ACI (Associate in Captive Insurance) are often required. Strong analytical thinking, attention to detail, and excellent client communication skills set top performers apart. These competencies are crucial for effectively managing captive insurance operations, ensuring compliance, and delivering value to clients.

What are common challenges faced by captive insurance managers in maintaining compliance and regulatory standards?

Captive managers often encounter challenges in navigating complex and evolving regulatory environments, as regulations can vary by jurisdiction and frequently change. Staying compliant requires ongoing education, meticulous record-keeping, and close collaboration with legal and financial teams. Additionally, managers must ensure timely and accurate reporting while balancing cost-effectiveness and risk management. Building strong relationships with regulators and leveraging compliance software can help reduce potential pitfalls and maintain the captive’s good standing.

What is the difference between Captive vs Insurance Agent?

AspectCaptiveInsurance Agent
CredentialsLicensed insurance agents, often with specific company trainingLicensed insurance agents, typically with broader industry certifications
Work EnvironmentWork primarily for one insurance companyWork independently or for multiple insurers
Employer & Industry UsageInsurance companies, captive agenciesIndependent agencies, brokerages
Search & Comparison IntentUnderstanding employment with specific insurersComparing career options in insurance sales

Captive insurance agents work exclusively for one insurance company, representing its products. Insurance agents may work independently or for multiple companies, offering a broader range of options. The key difference lies in employment structure and product representation, affecting career flexibility and product knowledge.

What are popular job titles related to Captive jobs in Florida?

For Captive jobs in Florida, the most frequently searched job titles are:

What job categories do people searching Captive jobs in Florida look for?

The top searched job categories for Captive jobs in Florida are:

Captive jobs near you
Infographic showing various Captive job openings in Florida as of August 2026, with employment types broken down into 91% Full Time, 6% Part Time, and 3% Contract. Highlights an 63% Physical, 9% Hybrid, and 28% Remote job distribution, with an average salary of $33,986 per year, or $16.3 per hour.

Captive Solutions Partner

Crumdale Specialty

Orlando, FL

$108K/yr

Full-time

Medical, Dental, Vision, Life, Retirement

Re-posted 13 days ago

Job description

About Crumdale Specialty:

Crumdale Specialty is a diversified insurance firm providing custom, self-funded healthcare solutions to a limited distribution network of brokers, consultants, and agents nationwide. Ranked on the Inc. 5000 Fastest Growing Companies and Best Workplaces, we leverage industry expertise, superior talent, data analytics, and a disruptive mindset to manufacture, underwrite, and administer agile, transparent, and cost-saving solutions. We optimize the fragmented health benefits supply chain to reduce health benefit costs and create better outcomes for employers and employees.

At Crumdale, people come first. We strive to make a positive impact on the people we serve. We believe this starts with the passion and purpose of our team. Our company culture is rooted in alignment, innovation, and integrity.

About the Job:

Crumdale Specialty is seeking a Captive Sales Advisor to partner with Regional Sales Directors to win alternative funding opportunities specifically by turning "captive" from a conceptual idea into a clear, financeready decision for employers.

This role elevates the effectiveness of our field teams by simplifying technical components of self-funding, captives, stoploss strategy, and cost-containment solutions. This role plays a critical part in shaping deal strategy, enabling producers, and ensuring that opportunities move efficiently from discovery to close.

Key Responsibilities:

  • Serve as the subject matter expert on complex captive and alternative funding cases.
  • Equip producers with concise talk tracks, discovery paths, and executive-friendly explanations of risk, funding mechanics, governance, and key tradeoffs.
  • Support regional sales leaders in positioning Crumdale's captive solutions competitively and effectively.
  • Build, activate, and maintain referral networks across brokers and consultants.
  • Make it simple for external partners to introduce captive strategies.
  • Deliver training, tools, and confidence-building resources that expand captive pipeline opportunities.
  • Coordinate with underwriting, operations, account management, and solution partners to ensure cohesive deal execution.
  • Translate discovery findings into credible proposals and ensure readiness for financial and operational evaluation.
  • Maintain disciplined timelines and ensure seamless handoffs into onboarding.
  • Bring structure to the alternative funding sales motion with clear KPIs, next steps, and progress tracking.
  • Help internal teams prioritize support based on probability to close.
  • Ensure opportunities do not stall in "maybe" by driving accountability and clarity throughout the process.
  • Develop field-ready materials that increase speed-to-proposal and close rates.
  • Contribute to internal training, content creation, and tools that simplify complexity for both buyers and brokers.
  • Represent Crumdale's captive capabilities with clarity and authority in the market.

Requirements

  • Deep experience in self-funding, group captives, stoploss strategy, and employer funding models (midmarket focus).
  • Background working within national brokerage platforms or highgrowth consulting environments.
  • Strong executive communication skills with ability to translate complex concepts into simple, defensible employer decisions.
  • Proven ability to partner with frontline producers and guide complex deals through a disciplined sales process.
  • Ability to orchestrate cross-functional teams from underwriting through operations to deliver accurate, timely proposals.
  • High commercial acumen and strong relationshipbuilding skills in both direct sales and channel environments.

Benefits

At Crumdale, we strive to provide a comprehensive and supportive benefits package to ensure the well-being of our employees. Our benefits include:

  • Medical
  • Telemedicine
  • Dental
  • Vision
  • Life, AD&D, Disability
  • 401(k)
  • Flexible Time-off

Please note: Crumdale Specialty is not engaging with external recruitment agencies; please refrain from contacting us regarding this position.

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