Captive Executive, Employee Benefits

Build a Market. Grow a Business. Make an Impact.

Innovative Captive Strategies (ICS) is seeking a highly motivated sales and relationship management professional to expand our Employee Benefits captive practice in strategic markets across the United States.

A high number of candidates may make applications for this position, so make sure to send your CV and application through as soon as possible.

This is not a role focused on maintaining an existing territory. It's an opportunity to develop one.

We're looking for someone who thrives on building relationships, creating opportunities, and driving growth. As a Captive Executive, you'll serve as a trusted advisor to benefits consultants, agency partners, and business leaders, helping organizations explore innovative approaches to healthcare financing and employee benefits while expanding ICS's market presence.

If you're energized by autonomy, consultative sales, and the opportunity to make a visible impact in a growing organization, we'd like to talk with you.

What You'll Do

Drive Business Growth

• Develop and execute market expansion strategies within assigned territories.
• Build relationships with employee benefits agencies, consultants, producers, and business leaders.
• Generate new business opportunities through strategic prospecting and consultative sales efforts.
• Lead conversations with prospective clients and agency partners to identify opportunities and deliver tailored solutions.
• Help employers explore alternatives to traditional fully insured health plans through captive and alternative funding solutions.

Serve as a Strategic Advisor

• Educate clients and partners on employee benefits captives, alternative funding strategies, self-funded health plans, and medical stop-loss solutions.
• Provide consultative guidance that helps employers gain greater control, transparency, and long-term value from their healthcare and employee benefits programs.
• Present complex concepts in a clear, practical, and business-focused manner.
• Help clients navigate rising healthcare costs through innovative and collaborative funding approaches.

Lead and Grow Captive Programs

• Serve as the strategic lead for employee benefits captive programs.
• Partner with employers, benefits consultants, agency partners, captive members, healthcare vendors, and strategic partners to support program growth and long-term success.
• Facilitate member meetings, educational sessions, and strategic planning discussions.
• Drive participation, engagement, and retention within captive programs.

Influence the Future

• Collaborate with leadership and internal teams to help shape captive strategy and market direction.
• Represent ICS at industry events, conferences, and business development initiatives.
• Mentor and support team members while fostering a collaborative, growth-oriented culture.

What We're Looking For

We're interested in accomplished relationship builders who have successfully developed new business opportunities, earned trust with decision-makers, and consistently delivered results.

Ideal candidates may come from:

• Employee Benefits Brokerage or Consulting
• Benefits Producer or Sales Leadership Roles
• Medical Stop-Loss
• Self-Funding and Alternative Funding
• Employee Benefits Captives
• Group Health and Welfare Benefits
• Healthcare Cost Management
• B2B Consultative Sales
• Business Advisory or Consulting Roles

Successful candidates typically:

• Excel at consultative selling rather than transactional selling.
• Enjoy building something from the ground up.
• Have strong business development and networking skills.
• Can confidently engage executives, owners, CFOs, HR leaders, and senior decision-makers.
• Operate independently while balancing strategy, relationship management, and execution.
• Understand how to connect business challenges with strategic employee benefits solutions.

Qualifications

• 6+ years of experience in employee benefits, insurance, business development, consulting, captive insurance, or a related field.
• Demonstrated success in consultative sales and relationship management.
• Employee benefits, health insurance, alternative funding, self-funded health plans, stop-loss, or benefits consulting experience preferred.
• Insurance licensing (or ability to obtain licensure within three months).
• Ability to travel up to 50%.

Why This Opportunity?

This role offers the chance to become the face of the business in a developing market while partnering with organizations that are looking for smarter, more strategic ways to manage healthcare costs and employee benefits.

You'll have the opportunity to:

• Build a market and establish a meaningful presence in your territory.
• Create and grow influential benefits agency and consultant relationships.
• Work directly with employers, executives, and decision-makers.
• Help organizations gain greater control over healthcare costs and benefits outcomes.
• Influence strategy and drive meaningful growth.
• Join a team that values entrepreneurship, collaboration, and long-term success.

If you're a proven relationship-builder who enjoys creating opportunities, developing partnerships, and driving growth, we'd love to connect.

Compensation is based on several factors, including, but not limited to, education, work experience, industry certifications, and is commensurate based on the book of business. xhyhwjd In addition to your salary, Holmes Murphy offers a comprehensive total rewards program including annual bonuses, total wellbeing benefits and support for professional development.