Leave Support Operations Specialist

Remote | Full Time | Start time between 9–10 am ET

About Empathy

Empathy is on a mission to help families through life’s most challenging moments. With an award-winning product, powered by tech and driven by purpose, we provide peace of mind by guiding families through the tedious and time-consuming tasks that loss and major life transitions can bring. Our team is passionate, empathetic, and committed to providing world-class care and support to families when they need it most.

About The Role

Empathy is seeking a thoughtful, resourceful Care Operations Specialist to help launch and scale our new chat-based support offering for users navigating short-term disability through our Empathy Leave Support product.

In this newly created role, you’ll partner closely with the Care Experience leadership team to build the operational foundation for excellent support—developing internal tools and training, refining workflows, and synthesizing feedback to shape our service. You’ll also step in directly to support users during escalations, fill support coverage gaps, and coach frontline Care Specialists as needed.

We’re looking for someone with a deep understanding of disability support systems who thrives in ambiguity, loves getting into the weeds to learn more about the subject, and brings a builder mindset. This is a mid-level individual contributor role with future growth potential into team leadership.

In this role you will:

Key Responsibilities

Operations & Enablement

• Build and maintain internal knowledge bases, workflows, and support templates
• Evaluate and adapt content and internal documentation to meet the needs of Empathy Leave Support users
• Consult on the creation of onboarding and training materials to support the success of Care Specialists responding to Leave Support users
• Partner with Care Experience leadership to define tone, escalation protocols, and best practices for chat-based support
  
  

Insights & Iteration

• Gather insights from users and the Care Team to inform product feedback loops and process updates
• Synthesize operational challenges and identify opportunities for improvement
• Support cross-training strategy for Care Specialists working across Empathy Leave Support, Loss, and future products
  
  

Frontline Support

• Handle escalated chats, research requests, and VIP user handoffs from Care Specialists
• Offer guidance and coaching to frontline team members on complex or high-sensitivity cases informed by statutory, federal and Client company policy
• Step in to chat during periods of high volume to ensure seamless user support
  
  

Requirements:

About You

Required:

• Deep understanding of the needs of individuals navigating disability products (e.g., from experience in disability services, public health, case management, or another field directly supporting this population)
• Strong critical thinking and problem-solving skills and developing analytical skills.
• Strong track record of operational success in enablement, or service design in a care- or support-oriented setting
• Ability to thrive in a fast-moving, ambiguous environment and build structure where it doesn’t yet exist
• Excellent written and verbal communication skills
• Comfort working across teams and balancing individual and team-based work
  
  

Preferred:

• Background in healthcare navigation, behavioral health, social work.
• Experience designing or delivering training content
• Familiarity with chat-based support
• Experience using platforms like Slack, Zendesk, Notion, and Google Suite
  
  

Compensation & Benefits

• Starting Salary Range: $60,000–$70,000 annually
• Company equity in a high-growth startup
• Annual remote work stipend
• Comprehensive health insurance
• Generous paid time off, including vacation days, company holidays, and bereavement leave
• 401(k) plan with employer match
  
  

Application Process

Candidates will participate in a multi-stage interview process, including conversations with peers and leadership. We value transparency, clarity, and thoughtfulness throughout the process.

Empathy is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive workplace for all employees.