Senior Director of Strategic Client Success

Join Headspace, a dynamic growth-stage company, as the Senior Director of Strategic Client Success. In this role, you will lead the Strategic Client Success group, overseeing a team responsible for our largest and most strategic employer relationships. You will set the vision and operating model for the team, coach and develop high-performing client executives, and partner cross-functionally to drive retention, growth, client outcomes, and long-term strategic value across the portfolio.

• Lead and develop the Strategic Client Success team, fostering a collaborative, high-performing culture by setting performance standards, coaching for excellence, and building bench strength across the team.
• Define and oversee the strategic account planning process across the Strategic Client Success portfolio, ensuring the team develops deep client partnerships that drive long-term value, retention, and growth.
• Own the team’s commercial performance, including renewals, revenue retention, expansion opportunities, utilization-based outcomes, and proactive risk management, with an emphasis on growing account value over time.
• Deep understanding of the mental health landscape, including industry trends, and payment models
• 12+ years of experience in a strategic client-facing role, such as Strategic Account Management, Customer Success, or Relationship Management
• Demonstrated track record of consistently meeting or exceeding revenue retention and growth targets
• High emotional intelligence and experience navigating sensitive, high-stakes client conversations with professionalism and strategic insight
• Proven experience managing a portfolio of large, complex accounts (Fortune 100 companies; 25,000+ employees and/or $1M+ in recurring revenue) including upsell and strategic renewal negotiations
• Strong business acumen and analytical skills, with the ability to use data to tell a compelling story and demonstrate ROI
• A confident, proactive self-starter who is comfortable “rolling up their sleeves” to figure things out in a fast-paced, growth environment
• Exceptional communication and presentation skills, with the ability to articulate complex concepts and value propositions to a variety of stakeholders, including C-level executives and consultants
• Experience partnering with Revenue Operations or CS Operations to build scalable processes and reporting
• Experience with Employee Assistance Programs (EAPs) required
• 3+ years of people leadership experience, including managing client facing Account Executives or Client Success professionals in a fast-paced environment working against revenue and retention targets