# Director, Stop Loss Market Relations

> Crumdale Specialty · Paoli, United States (Remote) · Full-time · Posted 2026-05-26

**Workplace:** remote

**Department:** Quoting/Pricing

## Description

**About Crumdale Specialty:**

Crumdale Specialty is a diversified insurance firm providing custom solutions to businesses nationwide. We leverage industry expertise, superior talent, and a disruptive mindset to provide agile, transparent, and cost-saving solutions to optimize self-funded health plans. Founded in 2014, we are the fastest-growing purveyor of integrated insurance solutions, with deep-rooted experience in program management, TPA administration, PBM consulting, stop-loss coverage, compliance, risk management, underwriting, and analytics.  

At Crumdale, people come first. Our clients, colleagues, trading partners, and communities are our strength. Our company culture is rooted in alignment, innovation, and integrity. We are proud to be named an Inc. Magazine Best Places to Work in multiple years. 

Reporting to the SVP of Stop Loss & Sales Operations, the Director of External Market Stop Loss Relations will act as Crumdale’s external market stop loss relationship subject matter expert responsible for developing new, and enhancing existing, relationships with external stop loss carrier partners. Working collaboratively and in the interest of Crumdale, drive detail, discipline, and accountability with external stop loss carriers with respect to communication, expectations, timelines, and results. The successful Director will increase the number of stop loss carrier partners and the number of competitive stop loss quotes produced by Crumdale through Crumdale’s Stop Loss Center of Excellence but is not accountable for the sale. 

The Director of External Market Stop Loss Relations will provide ongoing stop loss expertise to internal and external stakeholders to include working across various functional areas. This role will work on both tactical and strategic aspects of stop loss quoting and pricing for new business and renewals, working closely with Regional Sales Directors and Sales VPs. This role will also drive forward the orchestration and execution of stop loss related initiatives on behalf of the SVP of Stop Loss & Sales Operations, thereby extending the effectiveness of the organization.  

Duties & Responsibilities:  

-   Develop strong stop loss carrier partnerships with Crumdale’s existing stop loss partners as well as identify and cultivate new stop loss carrier partnerships.   

-   Implement new, and enhance existing, processes to improve efficiency and speed to quote while driving competitive performance from Crumdale’s stop loss partners. 

-   Mastery of Crumdale’s cost containment programs, how they impact plan pricing and their application to stop loss insurance.   

-   Work closely with the Pricing, Quoting, & Center of Excellence teams to develop proper quote requests and process to maximize impact to the organization.   

-   Negotiate proposals with and without direction to secure the best possible quotes prior to releasing to the sales team.   

-   Help the team drive more stop loss proposals to go firm and final and ultimately close as new sold business. 

-   Leverage technology and artificial intelligence to amplify the expertise of the team and Crumdale’s carrier partners, and accelerate quote throughput thus reducing time to quote at all stages of the process.

## Requirements

**Qualifications & Skills:**

-   Self-funded employee benefits industry experience with minimum 5 years’ experience in stop loss / medical reinsurance sales (10+ years’ preferred)
-   Extensive knowledge of, and relationships in, medical stop loss underwriting
-   Captive experience, preferred

-   Excellent communication, interpersonal, and organizational skills 
-   Superior critical thinking and analytic skills

-   Ability to form strong relationships with internal and external teammates 
-   Proven ability to lead and develop a high performing team

-   Ability to maintain a high level of confidentiality 

**Education:**

-   Bachelor’s degree in business, finance, and / or similar discipline with analytic basis\*

-   Experience with Salesforce, preferred
-   Proficient with MS Office suite 

\*Equivalent military service at E4 or higher is acceptable in place of a bachelor’s degree  
 

**Travel Requirement:**

-   Ability to travel overnight up to 20%, required

## 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.

## Apply

[Apply at Crumdale Specialty](https://apply.workable.com/crumdale-specialty/j/49709A4FD5/apply)

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