The Opportunity: Strategic Right Hand to the CEO

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. 

 

Key Responsibilities

1. 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.

1. CEO Leverage & Communication

• 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.

1. 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.

1. 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.

 

A Week in the Life of Kasa’s Chief of Staff

As Kasa’s Chief of Staff, no two days (or weeks!) look exactly the same. You’ll work side-by-side with the Founder & CEO, beginning each week by aligning on strategic priorities and dividing key initiatives between the two of you. You'll act as a force multiplier, amplifying leadership effectiveness, improving clarity across the organization, and ensuring nothing mission-critical falls through the cracks.

Throughout the week, you’ll lead key internal rhythms: the executive team’s weekly meeting, and organize our company-wide All Hands. You’ll represent the CEO in meetings, manage executive communications, and act as a liaison between internal teams and external stakeholders.

You’ll also take on complex, high-impact projects. These might include:

• Building board and fundraising materials
• Driving content and logistics for leadership summits or strategic offsites
• Deep diving into Kasa’s technology, product, or operational metrics
• Make recommendations for key strategic decisions at business inflection points
• Coordinating and executing cross-functional initiatives involving Finance, Legal, Real Estate, and Operations

This role requires someone equally comfortable with big-picture strategy and day-to-day execution. Someone who thrives in ambiguity, builds trust quickly, and knows how to move work forward across diverse teams.

 

What Success Looks Like

After one year, success in this role means you have:

• Earned deep trust from the CEO and leadership team as a reliable operator and thought partner.
• Delivered at least 5 high-impact, cross-functional projects that materially advanced Kasa’s strategic goals.
• Built or implemented systems that meaningfully improved team productivity, reporting quality, or data transparency.
• Elevated the operational cadence of the leadership team, driving greater clarity, accountability, and momentum.
• Developed a firsthand understanding of what it takes to run and scale a fast moving hospitality platform.

 

Qualifications

Required

• Bachelor’s degree in Business, Economics, Finance, Real Estate, or a related field. MBA preferred but not required.
• 5+ years of experience in management consulting, investment banking, private equity, or a high-growth startup leadership role.
• Exceptional analytical and communication skills: able to synthesize complex topics into crisp insights.
• You are an effective communicator and storyteller, in both written and verbal form, able to synthesize complex topics and engage with senior executives
• Proven ability to lead without authority, manage multiple projects simultaneously, and operate in ambiguity.
• Proficiency in Excel/Google Sheets, PowerPoint/Google Slides/Gamma, and business analytics tools.
• Proven ability to underwrite or analyze business and investment opportunities and translate insights into action
• Demonstrated fluency with AI platforms (ChatGPT, Notion AI, Gamma, etc.) and enthusiasm for leveraging technology to enhance output and efficiency.
• High emotional intelligence, executive presence, and confidence in leading meetings and facilitating discussion among senior leaders.
• Highly motivated, resourceful, and able to maintain efficiency while working independently in a fast-paced environment
• You are proactive by nature and are constantly looking for ways to enhance our company's product, culture, and results-oriented mindset.
• A self-starter mentality: proactive, humble, and intensely curious.

Preferred

• Prior experience as a Chief of Staff or operator to a C-Suite executive.
• Comfort with lightweight Vibe coding to get specific projects done.
• Deep interest in real estate, hospitality, or technology-enabled services.
• Ambition to lead a business or major function in the future.

 

Why This Role

This is not a traditional administrative Chief of Staff position, it’s a strategic apprenticeship in running a company.

You’ll sit at the nerve center of Kasa, working on everything from board decks to AI automations to leadership alignment. You’ll learn how decisions get made, what drives growth, and how to build systems that scale.

This role also provides a rare opportunity to participate hands-on in company-shaping events such as capital raises, M&A negotiations, and strategic partnerships, gaining exposure to both the analytical and relationship-management aspects of scaling a company.

If you’re eager to see how a technology-powered hospitality company operates from the inside and you’re ready to help shape its future then this role is for you.

Curious about the Kasa experience? Save 15% when you book on kasa.com

 

Benefits

• Remote Work: With flexibility as a core value, and over three-quarters of the team working remotely, Kasa employees can work from anywhere, including our Kasa’s across the country!
• Kasa Travel Credit: We love to travel! Kasa employees get an allowance of free stays with us in any of our locations, plus a discount on any night for friends and family.
• The Pay: The starting base pay for this role is $155,000 - 185,000 plus performance-based incentives and is set based on multiple considerations, including business needs, market demands, talent availability, experience, and unique skills and attributes. The exact offer would depend on your background, experience, and internal equity considerations. The base pay range is subject to change and may be modified. This role may also be eligible for equity, bonus, perks, benefits, and Kasa Travel Credits.
• Generous Stock Option Plan: At Kasa, our compensation philosophy is to offer a total compensation package that over-indexes on equity to encourage our team to think like owners (by being owners) and benefit from the value growth that our collective hard work creates. 
• Flexible PTO: Full-time exempt Kasa employees are encouraged to take time off as they need and see fit, ensuring that it’s not disruptive to their work.
• 401(k) Plan: As you invest in yourself and your future, Kasa invests in you too: we offer a generous 401(k) contribution match. 
• Health Coverage: We’ve invested in comprehensive health insurance options to help when you need it most.
• Other Perks: Qualifying full-time roles are eligible for a wi-fi stipend, cell-phone reimbursement, home office stipend, and more!