About the Senior Pricing Analyst at Headspace: The Senior Pricing Analyst will be a key contributor on the Actuarial & Pricing team, working closely with Sales, Finance, and Go-to-Market teams. This role owns deal-level financial modeling and underwriting, competitive pricing intelligence, and the analytical work that connects pricing strategy to commercial outcomes. This role directly influences pricing strategy both on the deal and enterprise level. Reporting to the Director of Actuarial Analytics & Pricing, this position plays a central role in how Headspace prices, positions, and wins in the market. The ideal candidate brings rigor to a fast-moving, non-traditional environment and is comfortable operating across both technical and business-facing workstreams. What you will do: Own and enhance Headspace's pricing strategy by upgrading assumption pipelines, testing assumptions, and optimizing pricing models with cross-functional teams. Build competitive pricing intelligence, turning market signals, win/loss data, and industry trends into recommendations for GTM leadership. Analyze engagement and financial data to connect price points to deal outcomes—win rates, renewals, and deal economics—including churn/renewal drivers. Translate analyses into clear narratives that equip client-facing teams to drive decisions. Support deal desk with financial analysis and documentation for pricing approvals. Partner with Finance to ensure pricing structures are consistent with revenue recognition standards and support audit-readiness. What you will bring : Required Skills: Bachelor's degree in Finance, Economics, Mathematics, Statistics, Actuarial Science, or a related quantitative field 5+ years as an actuary, pricing analyst, financial analyst, or similar Extensive financial modeling experience in Excel or Google Sheets Data analysis skills (proficiency in R, SQL, Python) Strong interpersonal skills to collaborate, mentor peers, and influence stakeholders Experience supporting sales or commercial teams in a deal desk, pricing, or strategic finance capacity Experience working in the healthcare industry. Preferred Skills: Background in digital health, employee
benefits, or value-based care—particularly mental health Familiarity with SaaS or subscription-based pricing models, including PMPM structures, tiered pricing, and usage-based constructs. Strong presentation, project management, and problem-solving skills Experience with end-to-end assumption setting: conducting studies, documenting findings, communicating results Proven ability to manage competing priorities and communicate analytical findings to non-technical audiences across cross-functional teams Location: We are currently hiring this role remotely in the US and Hybrid for San Francisco, CA. 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. If your primary residence is in the greater San Francisco Bay Area, this role follows our hybrid model, with 3 days per week in office to support in-person collaboration. Your recruiter will share more details. Pay &
Benefits : The anticipated new hire base salary range for this full-time position is $99,000-$138,000 + equity +
benefits. For candidates based in San Francisco, New York City, or Seattle, a separate salary range of $[premium min to premium mid] applies, consistent with our location-based
compensation philosophy. 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 #LI-REMOTE
