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:

We are seeking a highly skilled Sales Recruiter with proven experience recruiting Regional Sales Directors (RSDs) , broker‑facing sales executives , and producer‑channel leaders in the employee health insurance and stop‑loss ecosystem .

This role is ideal for someone who knows the competitive landscape, understands the unique profiles of successful consultative sales leaders in this space, and can strategically source, engage, and close top talent in a fast‑paced, high‑growth environment.

Key Responsibilities

Sales Talent Acquisition

• Full‑cycle recruiting for Regional Sales Directors, VP‑level sales roles, and other distribution‑focused positions across Crumdale’s specialty lines
• Proactively source high‑performing candidates with experience in:
• Stop-loss underwriting or distribution
• Captive sales
• Middle‑market and large‑group employee benefits
• PBM or healthcare cost‑containment solutions
• Broker/consultant channel sales
• Build and maintain talent pipelines across key markets to support ongoing geographic expansion

Strategic Recruitment & Market Intelligence

• Leverage deep knowledge of the employee health insurance ecosystem to identify target competitors and high‑value talent pools
• Maintain current intelligence on compensation ranges, incentive structures, territory configurations, and competitor go‑to‑market models
• Partner with TA leadership and hiring managers to define candidate profiles, refine role scopes, and advise on market‑based hiring strategies

Candidate Experience & Assessment

• Drive a high‑touch, personalized candidate experience from first outreach through offer close
• Assess candidate capabilities across:
• Broker relationship development
• Market penetration strategy
• Technical knowledge of funding arrangements and cost‑containment
• Revenue performance and pipeline discipline
• Facilitate interview processes with speed, clarity, and structured evaluation methods

Stakeholder Collaboration

• Partner closely with the VP of Talent Acquisition, sales leaders, and the executive team to forecast hiring needs and prioritize roles
• Provide regular reporting on pipeline health, search progress, and market insights
• Collaborate with HR and leadership to support onboarding and ramp‑success strategies for new RSD hires

Requirements

• 3+ years of recruiting experience, with at least 1 year focused on sales roles in the employee health insurance space
• Direct experience recruiting Regional Sales Directors or territory sales leaders in at least one of the following areas:
• Stop-loss
• Captive insurance
• PBM / pharmacy programs
• Self‑funded employer health plans
• Broker/consultant distribution
• Strong sourcing capability using LinkedIn Recruiter, Boolean search, CRM/ATS tools, and targeted market mapping
• Ability to build relationships with industry talent and maintain a steady pipeline across multiple markets
• Excellent communication, executive presence, and closing skills

Preferred

• Experience in a high-growth, private‑equity‑backed, or multi‑entity organization
• Knowledge of compensation design and incentives for insurance sales roles
• Existing relationships within national and regional brokerage firms (Gallagher, Marsh, OneDigital, Lockton, HUB, etc.)

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.

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