Crumdale Specialty is a diversified insurance firm providing custom, self-funded healthcare ... funded, captive, stop-loss, pharmacy solutions, and TPA solutions. * Cultivate and expand ...
Crumdale Specialty is a diversified insurance firm providing custom, self-funded healthcare ... funded, captive, stop-loss, pharmacy solutions, and TPA solutions. * Cultivate and expand ...
... in direct alignment with client operations. * Develops trusted partnerships with key insurance ... captive structure is preferred. * Preferred industry specialization, such as Construction, Healt ...
... in direct alignment with client operations. * Develops trusted partnerships with key insurance ... captive structure is preferred. * Preferred industry specialization, such as Construction, Healt ...
... in direct alignment with client operations. * Develops trusted partnerships with key insurance ... captive structure is preferred. * Preferred industry specialization, such as Construction, Healt ...
... in direct alignment with client operations. * Develops trusted partnerships with key insurance ... captive structure is preferred. * Preferred industry specialization, such as Construction, Healt ...
Associate Client Executive, Commercial Risk - IAS Mid-Atlantic
Bethesda, MD · On-site
$100K/yr
... in direct alignment with client operations. * Develops trusted partnerships with key insurance ... captive structure is preferred. * Preferred industry specialization, such as Construction, Healt ...
Associate Client Executive, Commercial Risk - IAS Mid-Atlantic
Bethesda, MD · On-site
$100K/yr
... in direct alignment with client operations. * Develops trusted partnerships with key insurance ... captive structure is preferred. * Preferred industry specialization, such as Construction, Healt ...
Director Captive Insurance information
See Silver Spring, MD salary details
$11.4K - $24.3K
0% of jobs
$24.3K - $37.2K
0% of jobs
$37.2K - $50.1K
0% of jobs
$56.8K is the 25th percentile. Wages below this are outliers.
$50.1K - $63.1K
48% of jobs
The median wage is $64.7K / yr.
$63.1K - $76K
12% of jobs
$76K - $88.9K
9% of jobs
$92.5K is the 75th percentile. Wages above this are outliers.
$88.9K - $101.8K
18% of jobs
$101.8K - $114.8K
4% of jobs
$114.8K - $127.7K
0% of jobs
$127.7K - $140.6K
0% of jobs
$140.6K - $153.5K
8% of jobs
$11.4K
$83.6K
$153.5K
How much do director captive insurance jobs pay per year?
As of Aug 18, 2026, the average yearly pay for director captive insurance in Silver Spring, MD is $83,596.00, according to ZipRecruiter salary data. Most workers in this role earn between $62,000.00 and $96,100.00 per year, depending on experience, location, and employer.
What are the roles and responsibilities of a director captive insurance?
A Director of Captive Insurance oversees the management and operation of a captive insurance company, which is an insurance company established by a parent firm to insure its own risks. Their responsibilities include regulatory compliance, financial oversight, risk assessment, and ensuring the efficient administration of the captive. They also interact with regulators, auditors, and company leadership to ensure the captive meets its intended goals and adheres to legal requirements. Additionally, they may help design insurance programs and analyze loss trends to optimize risk management strategies.
What are the key skills and qualifications needed to thrive as a director captive insurance?
To thrive as a Director of Captive Insurance, you need expertise in risk management, insurance regulations, and financial analysis, often backed by a bachelor's degree in finance, business, or a related field. Familiarity with insurance management systems, captive insurance software, and relevant certifications like ARM (Associate in Risk Management) or CPCU (Chartered Property Casualty Underwriter) is highly valued. Strong leadership, strategic thinking, and effective communication skills are essential for managing teams and collaborating with stakeholders. These skills are critical for effectively overseeing captive operations, ensuring regulatory compliance, and optimizing risk financing strategies.
What are the primary challenges faced by a director captive insurance when managing compliance across multiple jurisdictions?
A Director of Captive Insurance often faces the challenge of navigating complex and constantly evolving regulatory requirements that differ across jurisdictions. Staying compliant involves regularly monitoring changes in laws, maintaining thorough documentation, and coordinating with legal and compliance teams to ensure all filings and reporting deadlines are met. This role requires strong attention to detail, proactive communication with regulators, and the ability to adapt quickly to new compliance landscapes. Collaborating with external advisors and leveraging technology can help streamline these processes and mitigate risks.
What is the difference between Director Captive Insurance vs Underwriting Manager?
| Aspect | Director Captive Insurance | Underwriting Manager |
|---|---|---|
| Credentials | Insurance licenses, industry certifications | Insurance licenses, underwriting certifications |
| Work Environment | Corporate, captive insurance companies | Insurance companies, brokerage firms |
| Employer & Industry Usage | Captive insurance providers, risk management firms | Insurance carriers, brokerage firms |
The main difference is that a Director Captive Insurance oversees the management of captive insurance entities, focusing on risk retention strategies, while an Underwriting Manager handles the assessment and pricing of insurance policies within traditional insurance companies. Both roles require industry licenses and work within the insurance sector, but their focus areas and responsibilities differ significantly.
What are the most commonly searched types of Captive Insurance jobs in Silver Spring, MD?
The most popular types of Captive Insurance jobs in Silver Spring, MD are:
What job categories do people searching Director Captive Insurance jobs in Silver Spring, MD look for?
The top searched job categories for Director Captive Insurance jobs in Silver Spring, MD are:
What cities near Silver Spring, MD are hiring for Director Captive Insurance jobs?
Cities near Silver Spring, MD with the most Director Captive Insurance job openings:
Full-time
Medical, Dental, Vision, Life, Retirement
Re-posted yesterday
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:
As a Regional Sales Director, you will be a cornerstone of our growth strategy. This role demands a highly driven, organized, and strategic professional with a passion for sales, broker development, and consultative solution selling. You will be responsible for building strong broker relationships, managing a robust sales pipeline, and closing high-quality business aligned with our integrated health platform.
We're looking for a driven, broker-focused sales leader who knows how to win in the self-funded health plan space.
Requirements
- Drive regional revenue growth by developing and executing a strategic sales plan focused on health plan solutions to include level-funded, self-funded, captive, stop-loss, pharmacy solutions, and TPA solutions.
- Cultivate and expand relationships within the limited distribution network of brokers, consultants, and agents.
- Identify, develop, and close new business opportunities while strengthening existing partner relationships.
- Educate broker partners on the full suite of health plan solutions, including stop-loss, captives, and alternative funding strategies.
- Serve as a trusted advisor to brokers and consultants by delivering data-driven insights and strategic plan design recommendations.
- Collaborate cross-functionally with underwriting, actuarial, operations, and leadership teams to deliver competitive, customized proposals.
- Lead finalist presentations, strategy meetings, and executive-level discussions with brokers and employer groups.
- Maintain a disciplined pipeline management process, providing accurate forecasting and sales reporting.
- Monitor regional market trends, competitor activity, and emerging opportunities to proactively position solutions.
- Achieve and exceed assigned sales targets, growth metrics, and profitability goals.
- Ensure alignment with underwriting discipline and long-term profitability strategy.
- Represent at industry events, conferences, and broker functions to expand brand visibility and market presence.
- Uphold culture of alignment, innovation, and integrity in all external and internal interactions.
Requirements
- 5+ years of successful sales experience in self-funded health plans, stop-loss, employee benefits, or related health insurance markets.
- Demonstrated success building and managing broker/consultant relationships within a defined territory.
- Proven track record of consistently meeting or exceeding revenue and growth targets.
- Strong understanding of alternative funding arrangements, captives, cost-containment strategies, and employer health plan design.
- Ability to articulate complex health plan solutions in a clear, consultative, and value-driven manner.
- Experience navigating multi-stakeholder sales cycles and leading executive-level presentations.
- Strong pipeline management and forecasting discipline with CRM proficiency.
- Financial acumen with the ability to align growth with underwriting profitability.
- Entrepreneurial mindset with the ability to operate independently in a fast-paced, high-growth environment.
- Willingness to travel within assigned region as needed.
Success Metrics & KPIs
Performance in this role will be measured by:
- Achievement of annual new business revenue targets.
- Growth in broker/consultant partnerships within assigned territory.
- Pipeline volume, velocity, and forecast accuracy.
- Case submission activity and quote-to-bind ratio.
- Profitability and underwriting alignment of sold business.
- Retention and cross-sell/upsell penetration across full solution suite.
- Contribution to regional market share growth.
- Quality of broker engagement and brand presence in the territory.
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.