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Sales Recruiter

Crumdale Specialty, Paoli, CO, United States


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

Qualifications

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.)

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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