Chief of Staff, COO

The Team + The Role Pendo is building on more than a decade of leadership in improving society’s experience with software. The company is pursuing an ambitious growth journey, with a bold goal to become the essential platform for great software embedded in all software development. This work requires strong operational alignment across the business as Pendo scales from $300MM to $600MM in ARR over the next three years. As Chief of Staff to the Chief Operating Officer, you will serve as the COO’s primary strategic partner and an independent executor across company-wide priorities. You will drive cross-functional alignment, lead high-priority initiatives, and act as a proxy for the COO in key meetings. This role requires operational depth, executive presence, analytical rigor, and the ability to turn complex strategy into clear execution. This role is based in our Raleigh or NYC office. What this looks like day-to-day Strategic execution: Lead high-priority, cross-functional initiatives from conception through completion. Break down complex strategic goals into actionable plans, drive accountability, and ensure progress in a fast-paced environment. Operational oversight: Drive alignment across Sales, Post Sales, Finance, Demand Generation, Product, and Engineering. Identify friction in the business machine from demand capture through revenue recognition, determine root causes, and help drive resolution. Executive proxy: You attend key meetings on behalf of the COO, make informed decisions in the moment, and ensure follow-through on every action item. You represent the COO’s perspective with authority and clarity. Communication and reporting: Own critical communications that connect operational work to company strategy. Support the COO’s portion of Board of Director decks, executive meeting cadences, COO communications to employees, and cascading messages to front-line leaders. Change management: Act as a culture carrier during rapid growth and organizational evolution. Resolve cross-team friction, strengthen alignment, and help teams move through change with clarity and urgency. Office leadership presence: Maintain a regular presence in the Raleigh office, with three days per week as the minimum standard and five days preferred. Use that in-person presence to stay close to executive priorities, build trust across teams, and move critical work forward quickly. Who You Are Beyond the qualifications, we hire through a specific lens. These aren't buzzwords; they're the things we'll actually look for in how you talk about your work. You're a builder, not a maintainer. You're most energized when there isn't a clear path yet, and you get to define it. You don't wait for direction; you identify gaps, shape solutions, and drive them forward. At Pendo, great Chiefs of Staff don't just follow instructions; they operate as strategic advisors, influencing decisions, guiding stakeholders, and elevating how we work. You're AI-curious - genuinely. You're not using AI tools occasionally. You're rewiring how you work around them. You're faster, sharper, and more prolific because of it, and you bring that energy to everything; how you approach your work, how you prep, how you communicate, how you think. We want someone who sees AI as a multiplier, not a shortcut. Must-haves 10+ years of experience in a high-growth SaaS environment, with experience in Strategy, Revenue Operations, Finance, or a previous Chief of Staff role. Deep proficiency in at least one core business area such as Sales Operations, Finance, or GTM Strategy, with a broad understanding of the SaaS lead-to-cash lifecycle. Proven experience driving large-scale strategic projects and managing cross-functional stakeholders at the executive level. Strong executive presence and the ability to act as a trusted advisor, build relationships across diverse teams, and synthesize complex topics into clear, concise communications. Expert-level analytical skills, including the ability to analyze