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Regional Sales Director, Captives

Who We Are

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 Role

Reporting to the Senior Vice President of Sales, the Regional Sales Director, Captives will act as Crumdale’s captive subject matter expert and sales lead responsible for generating new business revenue and growing a profitable book of business. This role will identify and develop strong broker partner relationships, work through established distribution channels of existing health plan Regional Sales Directors, and established Crumdale preferred broker partners. The focus for this sales position will be mid-sized employers (generally 25-300 enrolled employees).

The Regional Sales Director, Captive will direct and coordinate all components for the development of new business to include working across various functional areas (underwriting, marketing, operations, account management, PBM, etc.). Crumdale’s Regional Sales Director, Captives will also drive forward the orchestration and execution of captive related sales initiatives on behalf of the Senior Vice President of Sales, thereby extending the effectiveness of the organization.

Key Responsibilities

  • Identify, educate, and develop strong broker partners
  • Mastery of Crumdale’s cost containment programs and their application for brokers and employers
  • Create a regional sales plan that will support the successful attainment of goals and quotas
  • Execute sales techniques focused on the full sales lifecycle from lead generation to closing
  • Communicate consistently across the sales team, leveraging internal relationships for collaborative team-selling
  • Build trust and alignment across the organization
  • Travel required as needed to adequately maintain relationships

Minimum Activity Expectations

  • 1st month: 1 week at our home office location in PA for formal training
  • Maintain 5-10 national broker relationships selling Crumdale’s captive solution
  • 100 calls and 150 emails per month minimum
  • Average 5 broker meetings per week
  • Average 10 quotes per week
  • Maintain pipeline equivalent to 5x for annual stop loss sales goal
  • Clean and accurate data in Salesforce and Outreach.io
  • Quarterly meeting with Executive team to review scorecards and progress to discuss activities, quotes, revenue, pipeline, etc.

Essential Qualifications & Skills

  • At least three (3) years of experience in health plan captive sales
  • Five (5) years’ experience in the self-insured market
  • Must possess strong negotiating skills and excellent written and oral communication skills
  • Bachelor’s degree preferred, or equivalent military service or work experience

Benefits

  • Medical insurance
  • Dental insurance
  • 401(k)
  • Flexible PTO

Average salary estimate

$100000 / YEARLY (est.)
min
max
$80000K
$120000K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

What You Should Know About Regional Sales Director, Captives, Crumdale Specialty

Crumdale Specialty is on the lookout for a passionate and experienced Regional Sales Director, Captives to join our team! We’re a dynamic insurance firm dedicated to providing custom, self-funded healthcare solutions to a selective network of brokers, consultants, and agents across the country. As the Regional Sales Director, you’ll step into an exciting role where you'll channel your expertise into fostering relationships with broker partners and growing our award-winning business. Reporting directly to the Senior Vice President of Sales, you’ll be at the forefront of Crumdale’s efforts to generate new business revenue and enhance the profitability of our offerings. You will dive into the mid-sized employer market, typically serving 25 to 300 enrolled employees, and will leverage our innovative cost containment programs to facilitate better health benefit outcomes. Your responsibilities will also include crafting a robust regional sales strategy, collaborating with various departments such as underwriting, marketing, and operations, and executing effective sales techniques throughout the full lifecycle. At Crumdale, we believe in building trust within our organization and with our clients, so effective communication and teamwork are crucial. You will travel as needed to maintain these relationships, further amplifying your impact. If you have at least three years of experience in health plan captive sales and a knack for negotiation and communication, we want to hear from you and explore how you can grow alongside us in a company culture that champions innovation and alignment.

Frequently Asked Questions (FAQs) for Regional Sales Director, Captives Role at Crumdale Specialty
What are the primary responsibilities of the Regional Sales Director, Captives at Crumdale Specialty?

The Regional Sales Director, Captives at Crumdale Specialty is responsible for generating new business revenue, fostering relationships with broker partners, and developing a strategic sales plan to achieve goals. This role includes executing sales techniques throughout the complete lifecycle while collaborating with various functional areas to enhance business development.

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What qualifications are needed for the Regional Sales Director, Captives position at Crumdale Specialty?

Candidates for the Regional Sales Director, Captives role at Crumdale Specialty should possess at least three years of experience in health plan captive sales and five years in the self-insured market. Strong negotiating skills and excellent communication skills are essential, along with a preferable bachelor's degree or relevant work experience.

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How does the Regional Sales Director, Captives contribute to Crumdale's mission?

The Regional Sales Director, Captives plays a vital role in Crumdale’s mission by strengthening broker relationships, educating partners on our cost containment programs, and ensuring we deliver superior healthcare solutions. Their success directly contributes to our overall goal of improving health benefit outcomes for employers and employees.

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What is the expected travel for the Regional Sales Director, Captives at Crumdale Specialty?

Travel for the Regional Sales Director, Captives at Crumdale Specialty is required as needed to cultivate and maintain strong relationships with broker partners. This may involve attending meetings and events to ensure close collaboration and alignment across the sales team and the organization.

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What benefits does Crumdale Specialty offer to its Regional Sales Director, Captives?

Crumdale Specialty provides a comprehensive benefits package for the Regional Sales Director, Captives, including medical and dental insurance, a 401(k) plan, and flexible PTO. This commitment to employee well-being reflects our company culture of putting people first.

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Common Interview Questions for Regional Sales Director, Captives
Can you describe your experience in health plan captive sales?

When answering this question, highlight your specific experiences in health plan captive sales, focusing on the roles you've held, the challenges you've overcome, and your success in generating leads and closing deals.

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How do you approach developing strong broker partnerships?

Outline your strategies for building relationships, emphasizing past experiences where you successfully developed partnerships. Discuss communication, trust-building, and how your approach aligns with Crumdale's culture.

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What sales techniques have you found most effective in your previous roles?

Discuss specific sales techniques you’ve employed, such as consultative selling or leveraging data analytics. Provide examples of how these methods have led to achieving targets or enhancing client satisfaction.

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What do you consider the most important factor when creating a regional sales plan?

Explain the importance of thorough market research, setting clear objectives, and understanding the needs of both the brokers and employers. Relate this back to Crumdale's goal of providing innovative solutions.

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Describe a time you faced a significant challenge in your sales career. How did you overcome it?

Share a concrete example that showcases your problem-solving skills and resilience. Outline the situation, your actions, and the outcome, demonstrating your capability in the face of obstacles.

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How do you keep your sales pipeline organized and up-to-date?

Discuss your methods for pipeline management, such as using CRM tools like Salesforce. Emphasize the importance of data cleanliness and accuracy in driving successful sales results for the company.

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Can you give an example of a successful team collaboration in your past roles?

Share an instance where you worked cross-functionally, highlighting the outcomes of your collaboration. Focus on communication and how your actions aligned with the goals of the broader organization.

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How do you stay current with industry trends and developments?

Discuss the resources you utilize, like industry publications, webinars, and networking events, to stay informed. Highlight how this knowledge has positively influenced your sales strategies and outcomes.

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What would you say is your biggest strength as a Regional Sales Director?

Identify a key strength that aligns with the responsibilities of the Regional Sales Director role. Explain how this strength has aided your success in previous positions and can benefit Crumdale.

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Why do you want to work for Crumdale Specialty?

Convey your enthusiasm for the company's mission and culture. Share specific reasons why you believe Crumdale’s values resonate with your personal and professional goals, making you a great fit for the team.

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EMPLOYMENT TYPE
Full-time, on-site
DATE POSTED
March 16, 2025

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