Job Overview
Location
Remote - USA
Job Type
Full-time
Category
Software Engineering
Date Posted
June 6, 2026
Full Job Description
đź“‹ Description
- • Partner with the Chief Product Officer to translate strategic priorities into clear operating actions across the product organization during active reorganization.
- • Turn cross-functional input into decision-ready insights for the CPO by identifying risks, dependencies, and organizational friction early, particularly during change events and reorg activity.
- • Lead high-priority special projects that fall outside existing functional lanes, ensuring delivery against scope, timeline, and defined outcomes.
- • Run core management rhythms across the product organization, including reviews, planning forums, and decision tracking to ensure follow-through on major commitments and critical smaller decisions.
- • Improve meeting quality, escalation discipline, and executive focus so the CPO can prioritize time on high-impact activities.
- • Align product operating rhythms with company-wide reporting and decision cycles during the reorganization period.
- • Translate the CPO’s leadership principles into everyday behaviors, rituals, and team norms to help product leaders adopt the expected operating model with consistency and credibility.
- • Detect cultural drift and organizational confusion early and take corrective action to reinforce a culture of discipline, focus, and capital efficiency.
- • Represent the CPO selectively in internal forums where alignment and context are needed, preparing communications and materials to ensure consistent messaging across the company.
- • Translate strategic direction and business constraints into clear operating implications for partner functions such as engineering, marketing, finance, and sales.
- • Operate with high autonomy in ambiguous environments, using influence rather than formal authority to drive execution and organizational alignment.
- • Maintain discretion and integrity while managing sensitive and confidential information related to executive decision-making and organizational change.
- • Demonstrate strong business acumen by connecting product performance metrics—such as user adoption, engagement, revenue growth, retention, and bookings—to operational execution and strategic outcomes.
- • Support executive decision-making through exceptional writing, synthesis, and analytical skills in high-stakes, fast-moving settings.
- • Collaborate as a team member first, prioritizing team strength over individual contribution and actively seeking feedback to drive continuous improvement.
- • Embrace experimentation, learn from mistakes, and remain open to new ways of working while maintaining a high tolerance for 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
- • 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
- • Experience operating in lender-governed, covenant-sensitive, private-credit-backed, late-stage, or post-merger/reorg environments
- • Strong project management skills with the ability to advance multiple high-priority initiatives simultaneously
- • Exceptional analytical, problem-solving, and critical thinking skills
🏖️ Benefits
- • Competitive compensation with bonus eligibility
- • Comprehensive medical coverage
- • Unlimited PTO
- • Wellness reimbursement
- • Professional development funds
- • Blended work environment supporting collaboration, flexibility, and team connection
Skills & Technologies
About Pluralsight, Inc.
Pluralsight, Inc. is an American technology workforce development company that provides an online learning platform focused on software development, IT operations, data, cybersecurity, and cloud computing. Founded in 2004 and headquartered in Draper, Utah, the company offers expert-authored video courses, skill assessments, and hands-on labs targeting individual technologists and enterprise teams. Its SaaS products measure proficiency across technology roles, recommend personalized learning paths, and supply analytics to help organizations close critical skills gaps, accelerate cloud adoption, and improve developer productivity. Pluralsight went public on NASDAQ in 2018 and was taken private by Vista Equity Partners in 2021.
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