• Serve as a trusted thought partner to the CEO on company strategy, capital allocation, and operational priorities. • Lead and organize weekly leadership meetings, bi-weekly All Hands, quarterly offsites, and key internal forums to ensure decisions translate into action. • Synthesize business performance insights and surface data-driven recommendations for the CEO and executive team. • Partner with the CEO and Executive Team on the front lines of strategic transactions, including M&A execution, fundraising processes, and investor diligence. • Support evaluation and integration of acquisition targets, analyzing financial models, operational synergies, and team structures to inform strategic decision-making and post-close integration planning. • Prepare and review board materials, investor updates, and internal communications. • Anticipate the CEO’s needs by managing workflows, surfacing critical issues early, and ensuring priorities are executed efficiently. • Represent the CEO in meetings when needed, providing follow-up and driving outcomes to completion. • Build or prototype lightweight tools, dashboards, or scripts that improve visibility, automate workflows, and support faster decision-making. • Design systems or processes to audit recurring operational data (e.g., monthly financials, OTA rankings, property performance). • Champion the use of AI across the executive and operations teams, using platforms like ChatGPT, Granola, Notion AI, Cursor or custom scripts to automate workflows, enhance communication, and improve team productivity. • Help shape the leadership team’s rhythm and culture through thoughtful agenda design, meeting facilitation, and consistent follow-through. • Approach every problem as if you were the CEO, balancing strategic perspective with a bias for execution.