Job Description

Who we Are:

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 a Inc. Magazine Best Places to Work in multiple years.

Position Summary:

The ERISA Attorney at Crumdale Specialty plays a critical role in advising clients on complex employee benefits and ERISA matters, delivering strategic legal guidance that supports compliance, risk mitigation, and long-term organizational success. As a key member of the legal team, this individual will contribute to high-impact client engagements, offering sophisticated counsel on plan design, fiduciary obligations, regulatory developments, and related benefits issues.

This role offers the opportunity for immediate client interaction, significant responsibility, and the autonomy to grow a specialized legal practice. The ERISA Attorney will collaborate with internal stakeholders and external partners to navigate nuanced legal challenges and craft tailored, forward-thinking solutions that align with each client’s business objectives. The ideal candidate will bring at least two years of substantive experience in employee benefits law and demonstrate strong analytical, communication, and problem-solving skills in a fast-paced, client-focused environment.

In addition, this position will include supervisory responsibilities over members of the Compliance Team, requiring strong leadership, mentorship, and team management capabilities.

Requirements

• Provide strategic legal counsel on the design, implementation, and ongoing compliance of employee benefit plans, with a focus on fiduciary obligations and regulatory frameworks under ERISA.
• Provide day-to-day leadership and guidance to members of the Compliance Team, ensuring effective workload management and professional development.
• Conduct regular team meetings and performance reviews to foster accountability, collaboration, and continuous improvement.
• Navigate complex legal and regulatory challenges, delivering actionable guidance that supports client objectives and mitigates risk.
• Draft, review, and negotiate a broad range of plan documents, service agreements, and compliance-related materials with precision and clarity.
• Monitor and interpret evolving legal standards and regulatory developments, translating them into proactive strategies for clients.
• Collaborate cross-functionally with internal teams including Underwriting, Sales, PBM, and Operations to ensure plan structures and solutions align with regulatory requirements and business goals.
• Advise on the legal implications of innovative plan designs, including reference-based pricing, direct provider contracting, stop-loss arrangements, and cost-containment strategies.
• Support the development and implementation of ERISA-compliant plan administration processes, including claims procedures, fiduciary governance, and required disclosures.
• Assist in resolving escalated compliance issues, regulatory audits, and benefits-related disputes, ensuring strategic resolutions that protect both client and organizational interests.
• Contribute to internal and external thought leadership by providing insights on legal trends, emerging regulations, and industry developments in the employee benefits space.

Qualifications & Skills :

• 3+ years of substantial experience in benefits and ERISA law, including plan design, implementation, and compliance.
• Strong academic credentials with a J.D. from an accredited law school, strongly preferred but not required
• Demonstrated experience in a mid-size to large firm or corporate setting.
• Exceptional analytical and writing skills with the ability to manage complex legal issues.
• Entrepreneurial mindset with a commitment to professional growth and client development.
• Excellent work ethic, attention to detail, and ability to work effectively in a team-oriented environment.

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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