Director, Total Rewards
Posted on July 20, 2025 (about 11 hours ago)
About the Director, Total Rewards at Headspace:
We’re looking for a strategic and experienced Director of Total Rewards to lead our global compensation and benefits function. This leader will play a key role in shaping our people strategy to support business goals, employee satisfaction, and long-term engagement.
As Director of Total Rewards, you’ll drive the development and execution of compensation and benefits strategies that are competitive, equitable, and aligned with Headspace’s values and culture. You’ll drive strategy, policies, structure and practices forward and partner cross-functionally to ensure that all total rewards programs are thoughtfully designed, well-communicated, and consistently delivered. We're looking for a Director that is excited by operating at both the strategic and executional levels, moving seamlessly between setting direction and rolling up their sleeves to implement programs and directly managing audits, analysis, data integrity, etc.
What you will do:
Total Rewards Strategy & Leadership
- Own and evolve the company’s global Total Rewards philosophy and framework to support attraction, retention, and performance.
- Provide strategic guidance to senior leadership and collaborate with key stakeholders across Finance, Legal, People Ops, People Business Partners and Talent Acquisition.
- Partner with Talent Development and Talent Acquisition to develop, evaluate, and align positions and job levels to Headspace’s career framework and compensation structure that guides career progression.
- Partner with Talent Acquisition to evaluate internal and external offers to attract and retain highly sought-after talent, including executives.
- Partner with finance and legal counsel on matters related to executive compensation, annual compensation, and Board preparation materials for Compensation Committee meetings.
- Effectively lead crossfunctionally across compensation, benefits, payroll, and equity administration functions.
Compensation
- Design and maintain competitive compensation structures across base salary, bonuses, equity, and sales and executive compensation.
- Establish clear compensation guidelines and maintain internal and external equity.
- Participate in and analyze market benchmarking and compensation surveys to ensure competitiveness.
Benefits
- Oversee the strategy and design of health, wellness, retirement (401k), time-off, and ancillary benefits.
- Optimize program value and employee experience while managing costs and vendor partnerships.
Equity & Stock Administration
- Manage day-to-day equity administration, grant processes, and long-term incentive programs in partnership with Finance and Legal.
- Ensure accurate documentation and global compliance with equity policies and regulations.
Analytics & Compliance
- Analyze compensation and benefits programs for effectiveness and ROI, making data-driven recommendations.
- Ensure compliance with local, federal, and international regulations.
- Support performance and compensation processes that enhance employee engagement and satisfaction.
- Manage related budget line items and expenses.
AI
- Drive AI best practices into rewards work to drive innovation, productivity, efficiency and excellence.
What you will bring:
Required Skills:
- 10+ years of experience in Total Rewards, including compensation, benefits, equity, and executive rewards.
- Ability to operate at a strategic level while also mastering the details.
- Experience managing with leadership excellence and strategic impact to drive programs and initiatives cross-functionally.
- Experience in high-growth environments; public company experience a plus.
- Strong equity administration expertise and familiarity with compensation committee preparation.
- Advanced Excel and analytics capabilities; comfort with systems like UKG, Greenhouse, TalentComp, and Charthop.
- Clear communication skills and the ability to influence across levels and functions.
- Must have experience and working knowledge of compensation and benefit survey systems and processes such as Pave, Mercer and Radford.
- Uphold operational excellence and proactively improve efficiency and innovation through the use of tools and AI.
Preferred Skills:
- Bachelor’s degree in HR, Business, Finance, or related field; MBA or Master’s degree preferred.
- Professional certifications such as CCP, CBP, or CEBS.
- Experience designing self-funded health plans or creative benefits strategies.
Location:
This is a hybrid role located in our San Francisco office, working 3 days per week from the office.
Pay & Benefits:
The anticipated new hire base salary range for this full-time position is $177,100.00-$230,000.00 + 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.
How to Apply
Please visit the job page on Greenhouse at https://job-boards.greenhouse.io/hs/jobs/6988870 and use the application form provided there to apply for this position.