Sr. Program Specialist, Risk & Compliance Operations

About the role

In this Sr. Program Specialist role, you will own the end-to-end risk and compliance program lifecycle for Membership Services, ensuring every member interaction meets legal, regulatory, data privacy, and operational risk standards. You will act as the central orchestrator for complex initiatives that touch Product, Health, Legal, Privacy, Engineering, and Operations, translating expert guidance into repeatable workflows and systems. Success in this position requires comfort with ambiguity, a methodical approach to planning, and the ability to manage sensitive requirements without needing to be a legal expert. You will embed compliance directly into product and operational workflows, reducing escalations and safeguarding the member experience. This role demands strong judgment, cross-functional influence, and rigorous follow-through in a fast-paced environment. You will continuously monitor outcomes, recommend proactive mitigations, and serve as the primary program partner for audits and change reviews. Your work will ensure Membership Services is operationally ready and resilient across new features, channels, and markets.

Key facts

What you'll do

Lead end-to-end risk and compliance programs for Membership Services by defining scope, milestones, owners, dependencies, decision points, and measures of success.

Build and manage cross-functional project plans for initiatives involving Product, Health, Legal, Privacy, Engineering, and Operations to create structure and accountability.

Partner upstream with Product and business teams to identify risks, assess operational impact, and embed Membership Services readiness into launches 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.

Serve as the primary Membership Services 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 to reduce unnecessary representative escalations.

Monitor operational risks, incidents, and program outcomes by using data and member insights to recommend and drive proactive mitigation strategies.

Partner with Legal, Privacy, Health, and other subject-matter experts to understand evolving requirements and ensure Membership Services policies, workflows, and systems remain current.

Translate complex requirements into clear program updates and tailor communication for operational, technical, and executive audiences.

Take ownership of ambiguous or complex initiatives from initial intake and planning through implementation, launch readiness, and post-launch stabilization.

Lead multiple stakeholders toward clear decisions, accountable owners, and measurable outcomes while managing operational risks and readiness gaps.

Evaluate and integrate emerging tools and approaches, including AI, into day-to-day workflows while maintaining high standards for accuracy, quality, and compliance.

Champion WHOOP's mission and performance and wellness values through disciplined program execution and partnership.

Requirements

You bring 3+ years of direct program or project management experience, with increasing ownership of complex, cross-functional initiatives.

You demonstrate strong command of program management fundamentals, including scope definition, project planning, milestone management, dependency tracking, risk and issue management, stakeholder alignment, and status reporting.

You have exposure to risk, compliance, privacy, consumer protection, health, or other data-sensitive environments, though deep legal or regulatory expertise is not required.

You have proven ability to take ambiguous or complex initiatives from initial intake and planning through implementation, launch readiness, and post-launch stabilization.

You have a track record of leading multiple stakeholders toward clear decisions, accountable owners, and measurable outcomes.

You have experience managing operational risks, identifying readiness gaps, driving mitigation plans, and escalating issues with sound judgment.

You have experience partnering with teams such as Legal, Privacy, Product, Engineering, Health, Security, or Operations.

You communicate excellently in writing and verbally, producing clear program updates and tailoring communication for operational, technical, and executive audiences.

You show strong analytical and problem-solving skills, including the ability to synthesize data, identify patterns, and turn findings into practical recommendations.

You are comfortable operating in a fast-paced, ambiguous environment while maintaining strong execution discipline, accuracy, and attention to detail.

You are committed to embracing and leveraging AI tools in day-to-day work while maintaining high standards for accuracy and quality.

You align with WHOOP's mission and have a passion for performance and wellness.

You are prepared to relocate if necessary to work out of the Boston, MA office.

Practical notes

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.

WHOOP is an Equal Opportunity Employer and participates in E-verify.