Senior Counsel, Labor and Employment

As Senior Counsel, Labor & Employment, you will be the lead attorney partnering with Headway’s People function to support a rapidly growing and national workforce. You will own day-to-day advice and counsel on employment matters while also working closely with the People team to enhance systems and processes to allow Headway to scale with speed and fidelity.  This is a unique opportunity to join a mission-driven healthcare technology company, work alongside passionate and talented colleagues, and grow in an environment where Legal is viewed as a strategic partner.

You will:

• Serve as the primary legal advisor to the People team and business leaders on the full range of L&E matters, including hiring practices, performance management, separations, leaves and accommodations, investigations, wage and hour compliance, and other key areas  
• Build L&E infrastructure – design and review People-related policies, procedures, and workflows to enhance efficiency and effectiveness
• Be the in-house subject matter expert, training HRBPs and People managers on L&E developments and best-practices
• Draft, review, and negotiate employment-related agreements and documents
• Represent the company, including managing outside counsel, in litigation and related disputes  

You’d be a great fit if:

• You have 5+ years of post-bar admittance legal experience with a deep understanding of L&E matters 
• You have meaningful in-house experience in a fast-paced, high-growth start-up environment
• You have a deep ability to build relationships and consensus with colleagues amid competing views 
• You have detail-obsession that drives clarity – without missing the forest for the trees
• You have a J.D. from an accredited law school and active bar membership in good standing (including ability to register as NY in-house counsel)

While we prefer candidates based in the New York metro area, we will consider exceptional candidates nationwide.

Compensation and Benefits:

The expected base pay range for this position is $179,200 - $280,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

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