Lead Counsel, HR Products, Insurance & Benefits

Overview

A growing technology company is seeking a highly motivated, business-minded attorney to join their Legal & Compliance team as Lead Counsel for HR Products, Benefits & Insurance. This role involves providing key legal guidance on insurance and benefits-related initiatives, partnering closely with Product, Sales, and Compliance teams. The position reports to the Deputy General Counsel, Products Legal.

Responsibilities

• Serve as the primary legal advisor for Benefits Administration, Insurance, PEO, and EOR product teams on U.S. and international insurance and benefits regulatory matters, including ERISA, COBRA, and Section 125 cafeteria plan rules
• Guide the company’s insurance licensing program
• Review and advise on vendor and partnership agreements involving insurance or benefits products
• Manage the corporate insurance program
• Collaborate with Product, Operations, Business Development, Sales, and Client Services teams to build and manage the product counseling function
• Navigate complex regulatory frameworks domestically and internationally to create scalable and innovative product solutions
• Promote a culture of compliance and integrity throughout company operations
• Provide general legal advice as needed
• Develop and deploy AI-powered tools to automate legal workflows, scale team output, and enable self-service resources for cross-functional partners

Requirements

• 5+ years of legal experience in a regulated space, preferably with ERISA-governed employee benefits, COBRA, and insurance regulatory law
• 2+ years in an in-house product counseling role
• Experience advising on legal issues in highly regulated industries
• Experience leading and advising teams across multiple global regions
• Law degree (JD or equivalent)
• Entrepreneurial mindset with a solution-oriented approach
• Comfortable experimenting with and building on AI tools
• Strong project management and organizational skills
• Excellent drafting, written, and verbal communication skills, with the ability to simplify complex legal concepts
• Strong analytical and problem-solving abilities
• A sense of humor

Preferred Qualifications

• Passion for navigating complex regulatory frameworks and finding innovative solutions

Compensation & Benefits

• Competitive salary range: $177,000 - $295,000 USD per year (US-based employees)
• Equity and benefits included
• Salary offers consider professional background, experience, and location

Location & Work Environment

• Based in San Francisco, CA
• The organization values in-office collaboration and expects office-based employees to work onsite at least three days per week

Equal Opportunity

The employer is committed to building a diverse and inclusive workforce and does not discriminate based on legally protected characteristics. Reasonable accommodations are provided for candidates with disabilities during the hiring process.