Senior Director, Strategic Client Success

About the Senior Director, Strategic Client Success  at Headspace:

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. 

What you will do:

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%).

What you will bring :

Required Skills:

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.

Location:

We are currently hiring this role remotely, ideally located near a major city in the US, and Hybrid for San Francisco (SF). Candidates must permanently reside in the US full-time. For candidates with a primary residence in the greater SF area, this role will follow our hybrid model. You’ll work 3 days per week from our office, allowing for impactful in-office collaboration and connection, while enjoying the flexibility of remote work for the rest of the week. Your recruiter will share more details about our hybrid model. 

Pay & Benefits :

The anticipated new hire base salary range for this full-time position is $153,990-$195,000 base + quarterly variable compensation + equity + benefits . 

Our salary ranges are based on the job, level, and location, and reflect the lowest to highest geographic markets where we are hiring for this role within the United States. Within this range, individual compensation is determined by a candidate’s location as well as a range of factors including but not limited to: unique relevant experience, job-related skills, and education or training.  Your recruiter will provide more details on the specific salary range for your location during the hiring process.

At Headspace, base salary is but one component of our Total Rewards package. We’re proud of our robust package inclusive of: base salary, stock awards, comprehensive healthcare coverage, monthly wellness stipend, retirement savings match, lifetime Headspace membership, generous parental leave, and more. Additional details about our Total Rewards package will be provided during the recruitment process. 

About Headspace

Headspace exists to provide every person access to lifelong mental health support. We combine evidence-based content, clinical care, and innovative technology to help millions of members around the world get support that’s effective, personalized, and truly accessible whenever and wherever they need it.

At Headspace, our values aren’t just what we believe, they’re how we work, grow, and make an impact together. We live them daily: Make the Mission Matter, Iterate to Great, Own the Outcome, and Connect with Courage. These values shape our decisions, guide our collaborations, and define our culture. They’re our shared commitment to building a more connected, human-centered team—one that’s redefining how mental health care supports people today and for generations to come.

Why You’ll Love Working Here:

A mission that matters—with impact you can see and feel

A culture that’s collaborative, inclusive, and grounded in our values

The chance to shape what mental health care looks like next

Competitive pay and benefits that support your whole self

How we feel about Diversity, Equity, Inclusion and Belonging:

Headspace is committed to bringing together humans from different backgrounds and perspectives, providing employees with a safe and welcoming work environment free of discrimination and harassment. We strive to create a diverse & inclusive environment where everyone can thrive, feel a sense of belonging, and do impactful work together. 

As an equal opportunity employer, we prohibit any unlawful discrimination against a job applicant on the basis of their race, color, religion, gender, gender identity, gender expression, sexual orientation, national origin, family or parental status, disability*, age, veteran status, or any other status protected by the laws or regulations in the locations where we operate. We respect the laws enforced by the EEOC and are dedicated to going above and beyond in fostering diversity across our workplace. 

*Applicants with disabilities may be entitled to reasonable accommodation under the terms of the Americans with Disabilities Act and certain state or local laws. A reasonable accommodation is a change in the way things are normally done which will ensure an equal employment opportunity without imposing undue hardship on Headspace.  Please inform our Talent team by filling out this form if you need any assistance completing any forms or to otherwise participate in the application or interview process.

Headspace participates in the E-Verify Program .

Privacy Statement

All member records are protected according to our Privacy Policy . Further, while employees of Headspace (formerly Ginger) cannot access Headspace products/services, they will be offered benefits according to the company's benefit plan. To ensure we are adhering to best practice and ethical guidelines in the field of mental health, we take care to avoid dual relationships. A dual relationship occurs when a mental health care provider has a second, significantly different relationship with their client in addition to the traditional client-therapist relationship—including, for example, a managerial relationship.  

As such, Headspace requests that individuals who have received coaching or clinical services at Headspace wait until their care with Headspace is complete before applying for a position. If someone with a Headspace account is hired for a position, please note their account will be deactivated and they will not be able to use Headspace services for the duration of their employment. 

Further, if Headspace cannot find a role that fails to resolve an ethical issue associated with a dual relationship, Headspace may need to take steps to ensure ethical obligations are being adhered to, including a delayed start date or a potential leave of absence. Such steps would be taken to protect both the former member, as well as any relevant individuals from their care team, from impairment, risk of exploitation, or harm.

For how how we will use the personal information you provide as part of the application process, please see: https://www.headspace.com/applicant-notice