Chief of Staff, CEO

Pendo is seeking a strategic, proactive Chief of Staff to serve as a trusted advisor and partner to our CEO. This highly visible role will help shape and advance company priorities, drive cross-functional alignment, and enable effective decision-making across the executive team. The ideal candidate is a sharp, analytical thinker who thrives in complexity, brings clarity to ambiguous situations, and moves seamlessly between strategy and execution. You’ll bring an independent and balanced point of view, build trusted relationships across the organization, and help translate the CEO’s and executive team’s priorities into meaningful business outcomes. This role is based in our Raleigh office and requires travel. What this looks like day-to-day Honestly, there is no day-to-day for this job -- that’s the point. We’re looking for a heat-seeking missile to direct at the company’s hardest problems. Yes, you’ll be a member of our C-team helping to maximize our team’s entire effectiveness including our strategy planning, goal-setting, etc. We’re not looking for a facilitator or agenda-creator. We’re looking for someone who can synthesize data, form opinions and tackle problems with minimal supervision. Strategic planning and operating cadence: Drive the company’s strategic planning and operating rhythm, including annual thematic goals and quarterly OKRs. Partner with executive leaders and program owners to establish priorities, track progress, and surface issues requiring leadership attention. Tackle the hard problems: Take on complex, high-impact problems with minimal direction. Identify root causes, bring together the right perspectives to shape the path forward, and drive the work to a measurable outcome. Turn executive priorities into measurable results: Translate critical priorities into coordinated action across the organization. Mobilize the right leaders, remove obstacles, establish accountability, and sustain momentum through delivery. Executive and board communications: Develop high-quality narratives and materials for board, investor, executive, and other high-stakes meetings. Distill complex information into clear, compelling communication tailored to the audience and desired outcome. Leadership meetings and offsites: Lead executive team meetings and offsites in close partnership with the CEO. Shape agendas around the highest-leverage business issues and facilitate focused discussion, debate, and decision-making. 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 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 Progressive experience in a technology, top-tier consulting, investing, or another high-performance environment. Experience partnering directly with a founder, CEO, or senior executive and personally owning enterprise-level initiatives from strategy through implementation. A track record of delivering measurable cross-functional business outcomes across complex, senior-stakeholder environments. Strong understanding of how product, go-to-market, customer experience, finance, and operations work together. Exceptional strategic judgment and analytical ability, including the ability to make sound recommendations with incomplete information. Executive presence with the ability to influence, align, and constructively challenge senior stakeholders. Excellent written and verbal communication skills, including the ability to produce decision-ready presentations and board materials. Nice-to-haves Experience across multiple company stages, from early growth through scaled operations. A combination of consulting, investing, or strategy experience and hands-on operating leadership. Experience with enterprise transformation, operating-model design, product-led growth, or multi-product SaaS. About Pendo Pendo was founded in 2013 by former product managers, who combined their heads and hearts to build something they wanted but never had as product managers: a simple way to understand and attack what truly drives product success. Our mission is to improve society's experience with software. Come join one of the fastest-growing startups, supported by best-in-class institutions like Battery Ventures, Salesforce Ventures, Spark Capital and Meritech. Pendo Core Values: Bias to Act, Hone Your Craft, The Team is Pendo, and Maniacal Focus. Location: Pendo is a hybrid culture. In-office 3 days per week unless designated remote. Compensation: The expected salary range for this role to be performed in Raleigh, NC is USD $203,000 - USD $244,000 base plus a bonus target and equity Benefits: Pendo offers highly competitive, employer-heavy coverage in the United States, including $0 premium options, strong 401(k) match, equity, and flexible time off. EEOC: We are an equal opportunity employer and believe having diverse teams where everyone brings their whole self to Pendo is key to our success. We welcome all people of different backgrounds, experiences, abilities and perspectives. Accessibility: Pendo is committed to working with, and providing access and reasonable accommodation to, applicants with mental and/or physical disabilities. If you think you may require an accommodation for any part of the recruitment process, please send a request to: accommodation@pendo.io. All requests for accommodations are treated discreetly and confidentially, as practical and permitted by law.