Chief of Staff

Kasa is the leading tech-enabled hotel and apartment hotel brand and manager. Kasa has built a hospitality operating system that fundamentally improves the profitability of hospitality assets while delivering a high quality, digitally forward experience to guests. We partner with owners of multifamily and boutique hospitality properties to deliver stylish, professionally managed accommodations to business and leisure travelers alike. We took the best that hotels and short‑term rentals had to offer and created a new class of hospitality that is well‑priced, reliable, and offers a large selection of great locations.

Unlike traditional hotel operators, we prioritize automation, AI‑driven pricing, and data‑driven decision‑making to optimize revenue and improve guest experiences.

Kasa is seeking a Chief of Staff to the Founder & CEO: a high‑impact, high‑visibility role at the intersection of strategy, operations, and leadership.

This position is ideal for a future CEO or senior operator who wants firsthand exposure to how a high velocity, tech‑enabled hospitality company is built and run.

You will be the CEO’s right hand, helping drive strategic priorities, streamline operations, and drive clarity and coordination across the leadership team. You will also bring a builder’s mindset: leveraging the latest AI tools and lightweight automation to solve real business problems, from scraping market data to auditing financial reports or optimizing team workflows.

This role requires both analytical rigor and emotional intelligence, someone equally comfortable facilitating executive meetings as they are creating a GPT‑driven dashboard or an automated reporting process.

This role can be based remotely but there is a strong preference for candidates located in or willing to relocate to Kasa’s HQ in New York City. The Chief of Staff will travel periodically to Kasa’s properties and partner locations to experience operations firsthand, build relationships with on‑site teams, and help identify opportunities for performance improvement and brand elevation.

• Strategic & Operational Leadership
• 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, providing follow‑up and driving outcomes to completion.
• AI, Systems, & Creative Problem‑Solving
• 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.
• Leadership Development & Culture
• 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.

As Kasa’s Chief of Staff, no two days (or weeks!) look exactly the same. You’ll work side‑by‑side with the…