Director of Customer Support

What you will do:

Strategic & Operational Leadership

• Forward-Thinking Planning: Develop a business plan for the member and provider experience that anticipates future growth and technological shifts.

• Scaling & Efficiency: Implement tools and processes to handle thousands of multi-channel tickets (chat, voice, email) per week while meeting cost-to-serve targets. Emphasis on customer care, quality management, workforce forecasting, scheduling, recruiting, coaching, quality assurance, and training.

• AI & Automation Integration: Lead the strategy for integrating AI-driven support tools to automate routine workflows, improve self-service, and enhance "high-touch" human interactions.

• Escalation Management & Root Cause Analysis: Manage escalation processes and collaborate cross-functionally to address the root causes of member and provider issues.

Team Development & Management

• Leadership: Grow a team of incredible Customer Support Managers, Member Advocates, and a Workforce Management (WFM) Analyst to support our members and provider community in solving everyday problems.

• Performance Management: Ensure the team meets OKRs, SLAs, and KPIs, including CSAT, chat first response time, and call answer rates.

• Mentorship: Foster career growth through regular coaching, consistent 1:1s, and feedback sessions.

Data & Quality Assurance

• Insights: Unlock support interaction data to provide actionable insights for Product, Sales, and Operations teams.

• Quality Control: Lead efforts in quality management, workforce forecasting, and training to ensure a consistent "white-glove" experience.

About you:

Experience: 6+ years of relevant experience, ideally in a fast-growth health, wellness, or benefits environment.

Industry & Operational Mastery: Ability to master the detailed ins-and-outs of our operations and the complex healthcare industry. You will use this knowledge to build, improve, and scale a concierge, white-glove support team that consistently delivers for both our members and provider community.

Technical Expertise: A Zendesk "ninja" with a deep understanding of their suite. You are also well-versed in leveraging AI/LLM tools to scale support operations.

Analytical Rigor: Exceptional ability to analyze daily/weekly metrics to find trends, drill-down into cases as needed, and to take decisive action.

Process Builder: You can translate "nitty-gritty" requirements into scalable processes, macros, and training materials.

People-First Leader: Excellent people manager and strong team player with a track record of working cross-functionally. You know how to identify, recruit, and maximize your team’s talent. People love working with and for you.

Talent Developer: You are dedicated to fostering your team members’ continued career growth through regular coaching, consistent 1:1s, actionable feedback sessions, and accessible mentorship during business hours.

EQ & Communication: Exceptional emotional intelligence and a master of change management. You communicate with clarity and purpose across all channels—ensuring the "why" behind every transition is as clear as the "how."

Benefits:

• Remote company with a fully distributed team – no return-to-office mandates

• Flexible vacation policy (and a culture of using it)

• Medical, dental, and vision insurance with 100% company-paid employee coverage

• 401(k) with company match, FSA, and HSA plans

• Paid parental leave

• Short and long-term disability, as well as life insurance

• Competitive stock options are offered to all employees

• Transparent compensation & formal career development programs

• Paid one-month sabbatical after 5 years

• Stipends for setting up your home office and an ongoing learning budget

• Direct positive impact on members’ lives – wait until you see the positive feedback members share every day