Chief of Staff - Product

Job Description: The Chief of Staff to the Chief Product Officer is a high-trust, high-leverage role at Pluralsight as we operate through active transformation. This role exists to increase the CPO's effectiveness by driving execution, surfacing risk early, translating strategy into operating action, and reinforcing the behaviors needed for the next phase of performance. This role is a strategic operator role for a leader who can bring structure to ambiguity, communicate with precision, and improve organizational performance through influence rather than formal authority. This leader plays a critical role in creating the strategy, coordinating delivery, and managing the business value and commercial performance of our core learning offering, including user adoption, engagement, revenue growth, retention, and bookings for their product line. This is not an administrative coordinator role and not a shadow VP Product role. Success comes from creating internal leverage for the CPO and ensuring product decisions visibly reflect business constraints, organizational priorities, and the demands of the reorg environment. The Chief of Staff will bring strong business acumen, organizational agility, and a high tolerance for ambiguity to operate effectively in a dynamic and capital-disciplined environment. Who you’re committed to being: You enjoy learning and are open to new ways of doing things. You are not afraid to be yourself, experiment, make mistakes and learn from them, ask questions, or voice your concerns. When communicating you are self-aware, insightful, and proactive. You are a team member first and individual contributor second. You are aware that high-performing teams are only as strong as their weakest link. You believe in continuous improvement and request frequent feedback from others. What you’ll do: Partner with the CPO to translate strategic priorities into clear operating action across the product organization during active reorganization. Turn cross-functional input into clear, decision-ready insight for the CPO; identify risks, dependencies, and organizational friction early, especially during change events and reorg activity. Lead high-priority special projects that do not fit neatly into existing functional lanes, ensuring delivery against scope, timeline, and outcomes. Run core management rhythms across the product organization, including reviews, planning forums, and decision tracking; ensure follow-through on major commitments and important smaller decisions so momentum does not stall. Improve meeting quality, escalation discipline, and executive focus so the CPO spends time where it matters most. Align product operating rhythms to company reporting and decision cycles during the reorg. Translate the CPO's principles into everyday behaviors, rituals, and team norms; help leaders across the product organization adopt the expected operating model with consistency and credibility. Detect cultural drift and organizational confusion early enough to correct course; reinforce a culture of discipline, focus, and capital efficiency consistent with the company's current operating context. Represent the CPO selectively in internal forums where alignment and context are needed but direct executive presence is not; prepare communications and materials that help the CPO deliver a consistent message across the company. Translate strategic direction and business constraints into clear operating implications for partner functions. Experience you’ll bring: Demonstrated experience supporting C-level or senior product executives in a strategic or operational capacity. Strong writing and synthesis ability, especially in ambiguous and high-stakes settings. Demonstrated judgment, discretion, and comfort operating without formal authority. Track record supporting executive decision-making, cross-functional execution, and change management. Strong project management skills with the ability to advance multiple high-priority initiatives simultaneously. Exceptional analytical, problem-solving, and critical thinking skills. Strong written and verbal communication skills with proven ability to influence and build relationships across functions. High integrity, discretion, and ability to manage sensitive and confidential information. Collaborative, adaptable, and comfortable operating in an environment of ambiguity and change. Requirements: 10+ years of progressive experience in Chief of Staff, strategy, business operations, transformation, consulting, or senior product-adjacent roles in SaaS. Experience operating in lender-governed or covenant-sensitive environments is helpful, though direct lender interaction is not part of this role. Private-credit-backed, late-stage, or post-merger/reorg experience is strongly preferred. Experience in large-scale, global, or complex organizational environments is preferred. This is a remote role; however, applicants located within 45 miles of our Westlake/Dallas, TX office should expect to work on-site Tuesday through Thursday, with remote flexibility on Mondays and Fridays. This approach enables more effective collaboration, quicker decision-making, and a stronger culture, while still providing flexibility. Why you’ll love working here: We work in a blended environment that supports collaboration, flexibility, and connection across teams. We are mission-driven, shaping the future of tech upskillling and delivering impact that matters. We foster a culture of inclusion and belonging, where everyone can contribute and thrive. We are always learning, creating an environment where you can take on new challenges, expand your skills, and grow with purpose. Benefits include competitive compensation, bonus eligibility, comprehensive medical coverage, unlimited PTO, wellness reimbursement, professional development funds, and more. About us: Pluralsight provides the only learning platform dedicated to accelerating the technology skills and capabilities of today’s tech workforce. Thousands of companies, government organizations and individuals around the world rely on Pluralsight to support critical technology skill development in areas that are crucial to innovation including artificial intelligence, cloud computing, cybersecurity, software development, and machine learning. We offer highly curated content developed by vetted technology experts, industry leading skill assessments, and hands on, immersive learning experiences designed to help individuals skill-up faster. Physical Requirements: This role is primarily performed in an office or home office setting and involves standard computer-based work. EEOC & Accommodations Statement: Bring yourself. Pluralsight is an equal opportunity employer. We evaluate qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, age, or veteran status. We also consider qualified applicants with criminal histories, consistent with EEOC guidelines and local laws. If you need an accommodation to apply, interview, or perform essential job functions, please visit the bottom of our website to learn how to request an accommodation. Learn more about our commitment to diversity, equity, inclusion, and belonging in our DEIB Report. The annual US base salary range for this role is $156,000 - $210,000 USD. Actual compensation will depend on location, skills, experience, and other factors. Additional benefits and bonuses may apply. Applications must be submitted within 90 days after the initial posting date to be considered. Please be aware of recruiting scams. We’ll only contact you from an @pluralsight.com email or verified channels. We never ask for sensitive personal info or payments as part of the hiring process. All openings are posted on our Careers page. #LI-JM2 Pluralsight provides the only learning platform dedicated to accelerating the technology skills and capabilities of today’s tech workforce. Thousands of companies, government organizations, and individuals around the world rely on our platform to support critical technology skill development in areas that are crucial to innovation, including artificial intelligence, cloud computing, cybersecurity, software development, and machine learning. We offer highly curated content developed by vetted technology experts, industry leading skill assessments, and hands-on, immersive learning experiences designed to help individuals skill-up faster.