Chief of Staff - Product

Pluralsight

1d•$156,000 - $210,000•Hybrid

About The Position

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.

Requirements

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.
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.

Responsibilities

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.