Sr. Program Specialist, Strategic Readiness

As a Sr. Program Specialist — Risk & Compliance Operations, you will lead cross-functional programs that ensure Membership Services is operationally ready to meet legal, regulatory, data privacy, and risk requirements in every member interaction.   Sitting within the Membership Services Strategic Programs team, you will bring structure, planning discipline, and strong execution to complex initiatives involving Product, Health, Legal, Privacy, Engineering, and Operations. You will lead cross-functional project teams from planning through implementation, translating expert guidance into scalable workflows, systems, tools, and processes that enable compliant, high-quality support for new products, features, channels, and markets.   Success in this role requires strong program management fundamentals and the ability to navigate complex or sensitive requirements. Deep legal or regulatory expertise is not required, but exposure to this field is a plug. RESPONSIBILITIES: - Lead end-to-end risk and compliance programs for Membership Services, establishing clear scope, milestones, owners, dependencies, decision points, and measures of success. - Build and manage cross-functional project plans that bring structure and accountability to complex initiatives involving Product, Health, Legal, Privacy, Engineering, and Operations. - Partner upstream with Product and business teams to identify risks, assess operational impact, and embed Membership Services readiness into the launch of new features, channels, products, or markets. - Drive program governance through clear status reporting, risk and issue management, stakeholder communication, decision tracking, and timely escalation. - Lead compliance readiness planning for Membership Services and serve as the primary MS program partner for audits, change reviews, and requirements related to risk and data handling. - Coordinate cross-functional plans to close readiness gaps, implement policy or process changes, and respond to compliance-related incidents and escalations. - Design and maintain scalable frameworks that embed compliance requirements directly into Membership Services workflows and reduce unnecessary representative escalations. - Monitor operational risks, incidents, and program outcomes, using data and member insights to recommend and drive proactive mitigation. - Partner with Legal, Privacy, Health, and other subject-matter experts to understand evolving requirements and ensure Membership Services policies, workflows, and systems remain current. QUALIFICATIONS: - 3+ years of direct program or project management experience, with increasing ownership of complex, cross-functional initiatives. - Strong command of program management fundamentals, including scope definition, project planning, milestone management, dependency tracking, risk and issue management, stakeholder alignment, and status reporting. - Exposure to risk, compliance, privacy, consumer protection, health, or other data-sensitive environments is strongly preferred; deep legal or regulatory expertise is not required. - Proven ability to take ambiguous or complex initiatives from initial intake and planning through implementation, launch readiness, and post-launch stabilization. - Track record of leading multiple stakeholders toward clear decisions, accountable owners, and measurable outcomes. - Experience managing operational risks, identifying readiness gaps, driving mitigation plans, and escalating issues with sound judgment. - Experience partnering with teams such as Legal, Privacy, Product, Engineering, Health, Security, or Operations. - Excellent written and verbal communication skills, with the ability to produce clear program updates and tailor communication for operational, technical, and executive audiences. - Strong analytical and problem-solving skills, including the ability to synthesize data, identify patterns, and turn findings into practical recommendations. - Comfortable operating in a fast-paced, ambiguous environment while maintaining strong execution discipline, accuracy, and attention to detail. - Strong commitment to embracing and leveraging AI tools in day-to-day work while maintaining high standards for accuracy and quality. - Alignment with WHOOP’s mission and passion for performance and wellness. This role is based in the WHOOP office located in Boston, MA. The successful candidate must be prepared to relocate if necessary to work out of the Boston, MA office. Interested in the role, but don’t meet every qualification? We encourage you to still apply! At WHOOP, we believe there is much more to a candidate than what is written on paper, and we value character as much as experience. As we continue to build a diverse and inclusive environment, we encourage anyone who is interested in this role to apply. WHOOP is an Equal Opportunity Employer and participates in E-verify https://www.e-verify.gov/to determine employment eligibility   The WHOOP compensation philosophy is designed to attract, motivate, and retain exceptional talent by offering competitive base salaries, meaningful equity, and consistent pay practices that reflect our mission and core values.   At WHOOP, we view total compensation as the combination of base salary, equity, and benefits, with equity serving as a key differentiator that aligns our employees with the long-term success of the company and allows every member of our corporate team to own part of WHOOP and share in the company’s long-term growth and success.   The U.S. base salary range for this full-time position is $60,000 - $80,000. Salary ranges are determined by role, level, and location. Within each range, individual pay is based on factors such as job-related skills, experience, performance, and relevant education or training.   In addition to the base salary, the successful candidate will also receive benefits and a generous equity package. These ranges may be modified in the future to reflect evolving market conditions and organizational needs. While most offers will typically fall toward the starting point of the range, total compensation will depend on the candidate’s specific qualifications, expertise, and alignment with the role’s requirements.