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’re seeking an HR Generalist with strong payroll experience to join our HR team. In this role, you will take ownership of the end-to-end payroll process, ensuring accurate, timely, and compliant payroll for all employees. You will also support a few additional HR functions to enhance the overall employee experience, but payroll will be the primary focus.
Key Responsibilities:
Payroll Administration (Primary Focus)
- Maintain and update employee data in the payroll system to ensure accuracy and compliance
- Collect, validate, and input payroll-related data such as hours, bonuses, deductions, and adjustments
- Process payroll on a regular schedule, ensuring timely and accurate payments - Semi monthly
- Prepare payroll documentation for audits, reconciliations, and reporting purposes
- Respond to employee payroll inquiries and resolve issues professionally and efficiently
- Stay current on payroll regulations and best practices, recommending process improvements as needed
- Collaborate with HR and finance teams to ensure seamless payroll operations
Additional HR Support (Secondary Focus)
- Maintain accurate employee records in HR systems and ensure compliance with internal policies and regulations
- Assist with onboarding logistics, benefits administration, and basic HR inquiries as needed
- Support HR initiatives and projects that improve employee experience and operational efficiency
Requirements
- Proven experience managing payroll processing
- 2-3 years of HR experience, preferably in a high-growth or start‑up environment
- Strong knowledge of HR compliance, labor law, and benefits administration
- Experience with HR software, payroll interfaces, and benefits platforms (Paylocity and Workable preferred)
- Excellent communication, interpersonal, and organizational skills; ability to navigate ambiguity and build trust
- Comfortable working in a hybrid, entrepreneurial culture
Preferred:
- Experience in the self‑funded insurance or healthcare industry
- HR certification (aPHR, PHR, SHRM‑CP, etc.)
- Familiarity with analytics-driven HR and data tracking
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.
Top Skills
What We Do
Crumdale Specialty is a diversified insurance firm providing custom, self-funded healthcare solutions to a bespoke set 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. Our company culture is rooted in alignment, innovation, and integrity. We believe when our clients win, we win. We become part of your team, so you can do what you do best.









