Senior Director, Strategic Client Success

Headspace

1d•$153,990 - $195,000•Hybrid

About The Position

This is an exciting career opportunity at a dynamic growth-stage company. In this role, you will lead Headspace's 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. As a senior leader, you will serve as an executive partner to key customer stakeholders while shaping the strategy, processes, and capabilities that enable the team to consistently deliver measurable business impact.

Requirements

12+ years of experience 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, including managing client facing Account Executives or Client Success professionals in a fast-paced environment working against revenue and retention targets.
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 an 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%).