Chief of Staff to the CEO

Work directly with Sycamore’s CEO to turn priorities into action, keep the company moving, and make sure the things that matter actually get done. Based in Palo Alto, working primarily in person alongside the CEO and leadership team. About Sycamore Sycamore is building the trusted agent operating system for the enterprise. Our platform helps companies build, deploy, and orchestrate agentic apps that take on real operational work, with the security and control large organizations need. We are a small, engineering-led team working directly with Fortune 500 enterprises. We have raised $65M from Coatue and Lightspeed, along with other investors and industry leaders. The role The Chief of Staff works directly with the CEO across the highest-priority things happening at Sycamore. Your job is to create leverage: keep priorities clear, make sure decisions turn into action, and close the gaps that appear when a company is moving quickly. This is not a traditional operations role, and you do not need to have been a Chief of Staff before. We are looking for someone early to mid-career who is sharp, highly organized, an exceptional communicator, and comfortable moving between strategic work and execution. The scope will change with what the company needs. You might prepare the CEO for an important customer or investor meeting, coordinate communication across the company, research a strategic question, drive follow-up on a company priority, or build a lightweight automation that removes work from the team. The common thread is follow-through. You should be someone who naturally sees what needs to happen next, creates clarity when things are messy, and makes sure important things do not get dropped. What you will do Keep a clear view of the CEO’s priorities and make sure the work behind them keeps moving. Prepare the CEO for important internal, customer, investor, and partner meetings with the context, materials, and decisions needed going in. Turn meetings and conversations into action by capturing decisions, assigning owners, tracking commitments, and driving follow-through. Coordinate internal and external communication so the right people have the right context at the right time. Draft clear, concise communications on behalf of the CEO for employees, customers, investors, and other stakeholders. Jump into strategic questions, research, analysis, planning, and special projects as priorities change. Surface issues early, close open loops, and take ownership of work that does not yet have an obvious owner. Be AI-native. You use AI as a core part of how you work and are willing to build, automate, and create when needed. What we are looking for Typically 2-6 years of relevant professional experience in strategy consulting, investing, startup operations, or another analytical and strategic role. Exceptional written and verbal communication. You can take a messy set of ideas and turn them into something clear, concise, and useful. Strong judgment about context, audience, and tone, including when communicating on behalf of a CEO. Sound judgment and discretion when handling confidential company, employee, customer, and investor information. High attention to detail and exceptional follow-through. You keep track of commitments and make sure they get closed. Strong strategic and analytical instincts. You can quickly understand a new problem, structure it, and determine what matters. Comfortable working across senior executives, employees, customers, investors, and external partners. AI-native in how you work. You actively look for ways to use AI, automation, and lightweight tools to work faster and better. Comfortable with ambiguity, changing priorities, and taking on work outside a predefined job description. Low ego and willing to move between high-level strategic work and the small details required to make something happen. An MBA or similar experience can be helpful, but is not required. Interview process A 30-minute introductory conversation. Two 60-minute conversations focused on judgment, communication, strategic problem solving, and how you operate in ambiguous situations. A working session based on a real CEO or company priority, where you organize the problem, communicate your approach, and show how you would drive it through execution. Why join Work directly with the CEO on the priorities and decisions shaping Sycamore. Get exposure to nearly every part of building an early-stage enterprise AI company. Take on meaningful responsibility early, with scope that grows with what you demonstrate. Learn quickly in an environment where the feedback loop is short and the work changes as the company grows. Help build how an AI-native company operates, not just the product it sells. Receive competitive cash compensation and meaningful equity in the company you are helping build. #J-18808-Ljbffr