Executive Leader, Strategic Client Success (Remote)

Headspace; United States; Remote; USD 153,990 - 195,000; Full time

Job summary

Headspace is seeking a Senior Director of Strategic Client Success to lead the Strategic Client Success group and oversee a portfolio of large employer relationships. You will set the vision and operating model, coach senior client executives, and partner cross‑functionally to drive retention, growth, and measurable business impact.

The role requires 12+ years in strategic client facing roles, strong leadership, and executive communication.

Qualifications

• 12+ years in a strategic client-facing role such as Strategic Account Management, Customer Success, or Relationship Management.
• Experience with Employee Assistance Programs (EAPs) required.
• 3+ years of people leadership experience managing client-facing Account Executives or Client Success professionals in a fast-paced environment.
• 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.
• Demonstrated track record of consistently meeting or exceeding revenue retention and growth targets.
• Strong business acumen and analytical skills, with the ability to use data to tell a compelling story and demonstrate ROI.
• Deep understanding of the mental health landscape, including industry trends and payment models.
• 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.
• High emotional intelligence and experience navigating sensitive, high-stakes client conversations with professionalism and strategic insight.
• A confident, proactive self-starter who is comfortable “rolling up their sleeves” to figure things out in a fast-paced, growth environment.
• Experience partnering with Revenue Operations or CS Operations to build scalable processes and reporting.

Responsibilities

• 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.
• Serve as the primary point of contact for the CS Center of Excellence, partnering closely with Revenue Operations and Strategy & Operations to build scalable processes, playbooks, and reporting infrastructure across the Strategic Client Success segment.
• Cultivate trusted relationships with key customer C-suite and senior stakeholders, serving as a strategic advisor while coaching the team to deepen executive engagement across the portfolio.
• Strengthen Headspace's consultant and broker strategy by fostering executive relationships with key consultants, brokers, and other third-party partners that influence client success and growth.
• Serve as the Voice of the Customer and lead cross-functional collaboration across Product, Clinical, Marketing, Operations, Support, and other teams to advocate for client needs, drive strategic initiatives, resolve escalations, and deliver an exceptional client experience.
• Establish the team’s executive business review strategy and standards, using data-driven insights, ROI metrics, and KPIs to demonstrate value, inform strategy, and guide client decision-making.
• Oversee portfolio health, forecasting, and operational rigor, ensuring accurate account plans, pipeline management, and client data integrity in all appropriate systems, including Salesforce.com.
• Travel to meet with clients (25–30%).

Skills

Strategic account management

EAP experience

People leadership

Large accounts

Revenue retention

Analytical thinking

Mental health knowledge

Executive communication

Emotional intelligence

Self-motivation

Revenue/CS Ops collaboration

Job description

Headspace is seeking a Senior Director of Strategic Client Success to lead the Strategic Client Success group and oversee a portfolio of large employer relationships. You will set the vision and operating model, coach senior client executives, and partner cross‑functionally to drive retention, growth, and measurable business impact.

The role requires 12+ years in strategic client facing roles, strong leadership, and executive communication.