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Nailing Cold Outreach for Captive Insurance

A Guide For Independent Agents

December 23rd, 2024

4 min read

By Jerrett Phinney

Nailing Cold Outreach for Captive Insurance Hero Image
Nailing Cold Outreach for Captive Insurance
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Talking about captive insurers can be intimidating, especially in cold-contact scenarios. Knowing where to begin can feel like finding a new location without a map. Success lies in knowing who to contact. Targeting businesses in familiar industries and understanding their specific needs can help independent agents like you make the process more focused and productive. 

This article explains how to identify businesses most likely to benefit from captives. It also discusses the characteristics of ideal clients, how to customize your outreach, and strategies for overcoming common challenges in cold contacting. 

Why Cold-Contact Prospects About Captives?

You might feel like Sysiphus is continuously rolling a rock at the top of a mountain when it comes to cold contact, or you might feel like it’s a continuous uphill battle. Thankfully,  reaching out to similar industries you’ve already worked with is an easy way to leverage your expertise. 

Captives provide insurance solutions for businesses seeking cost control, transparency, and flexibility. Once you understand what makes a business a good candidate, you can position captives as a logical next step for their operations. 

Identifying and Engaging Ideal Captive Clients for Cold Outreach

When cold contacting prospects, focus on industries or businesses that align with these characteristics:

1. Financial Investment in Insurance

  • Target Clients: Businesses spending $250,000+ annually on general liability, workers’ compensation, and auto liability.

Why this matters:

  • These businesses are likely feeling the pinch of rising premiums and are looking for ways to cut costs without sacrificing coverage.
  • Businesses at this scale often face unique risks that off-the-shelf policies don’t address. Captives offer solutions that align with their business’s specific needs. 
  • Businesses spending this amount annually meet the financial thresholds required to qualify for common captive structures, such as group captives, single-parent captives, or cell captives.

    2. Industry Familiarity

Start with what you know. Focus on industries you’ve successfully served in the past with success. You can cold contact with an email like this:

Subject: [First Name], An Insurance Solution for [Industry Name]

Hi [First Name],

I’ve worked with several [industry] businesses like yours and understand how rising insurance costs and specific policies can stifle growth. Thankfully, there’s a better way to take control.

With captive insurance, businesses like yours can:

  • Lower premiums by retaining underwriting profits.
  • Customize coverage to address risks unique to your operations.
  • Gain stability in pricing, even in volatile markets.

For example, one [industry] business I worked with reduced their insurance costs by 25% in the first year using this approach.

I’d love to discuss whether captive insurance could help your business achieve similar results. Would you be available for a quick call next week?

Click here to schedule a time, or reply to this email with your availability.

Looking forward to connecting!

[Your Name]”

Your experience in these sectors will build credibility and make it easier to demonstrate how captives could fit their needs.

Cold contacts work best when they don’t feel cold. You know their pain points. Are they dealing with rising premiums? Are they expanding and taking on new risks? This intel can help you craft a more personalized message.

Credibility is everything in cold outreach. Mention your past success within their industry or highlight your expertise in captives. Be honest and transparent about the benefits and drawbacks of captive insurance. You gain more credibility when you aren’t hiding anything from potential clients.

3. Entrepreneurial Mindset

Look for owners who:


  • Have built their business from the ground up.
  • Value innovative solutions over status quo insurance.
  • Believe in investing in risk management for long-term savings.

4. Frustrations with Traditional Insurance

You can ask questions such as:

Your goal in cold outreach is to open a dialogue. Use questions that prompt prospects to share their frustrations, such as:
  • “How do you feel about the control you currently have over your insurance spend?”
  • “Have you found your current coverage keeps with your business’s growth?”

Look out for and listen to those who:

  • Have Complaints about a lack of transparency.
  • Are frustrated over cookie-cutter policies that don’t fit their needs. 
Are sick and tired of rising premiums without corresponding claims. 

5. Commitment to Risk Management

Prospects should have:




  • A loss ratio of under 40% over the last five years.
    • One bad year is not a deal-breaker. Every business will likely have a bad claims year, one out of every five or six years
  • Basic risk management programs in place or a willingness to adopt them.
  • Claims that reflect proactive safety efforts.

Overcoming Cold-Contact Challenges with Captive Insurance

Like with any cold contact, you can't expect everything to go in your favor. Here are some challenges you'll likely face and how to address them:

Misconceptions About Captives

Many misconceptions about captives have perpetuated themselves over the years. Many prospects think captives are only for large corporations or overtly risky. Break these down in simple terms:

  • Captives can work for businesses spending at least $250,000 on premiums.
  • They aren’t inherently riskier than traditional insurance; they simply require proactive risk management

Handling Rejections Gracefully

Not every prospect will be ready or willing to go toward captive insurers. And that’s okay! Captives don’t work for everyone, anyway. 

Rejections are learning opportunities that allow you to refine future approaches. You can always leave the door open for future conversations by providing resources or offering to revisit the topic later. 

Tools to Simplify Cold Contacting

While cold contacting potential clients can already be intimidating, there are ways to make it easier for you when you have access to materials.

1.Case Studies


Prepare case studies from similar industries showing how captives solved real problems.

  • Example: “One of our manufacturing clients reduced their premiums by 28% in two years while gaining greater control over claims.”

2. Educational Materials


You can provide free resources such as what’s offered with Captive Coalition’s Learning Center to explain captives in an easy and palatable way. 

3. Follow-Up Plans


Cold outreach is rarely a one-call close. Develop a follow-up sequence that builds on the initial conversations. 

  • Example: A follow-up email could include a brief video explaining an invitation to a webinar or the benefits and drawbacks of a captive.

Access Resources for Captive Cold Calls and Learning Materials

Cold-contacting businesses about captives doesn’t need to be intimidating. By focusing on industries you better understand,  you can educate and offer captives to potential clients. 

Captive Coalition can provide you with educational and other resources. To start, look at our guide on how you can help educate your clients about captives with confidence

At Captive Coalition, our sole purpose is to educate independent agents about captive insurance so that they can best serve their clients. Our members have access to tools and email templates, including those used for cold emailing businesses.

To access the email templates and other exclusive materials like our tools and 30-day guide, become a member of Captive Coalition. That way, your best clients can have more control over their insurance costs.