Chief of Staff

ResortPass is redefining what it means to be a hotel guest. We're building a new category in hospitality: day access to luxury hotel experiences from breathtaking pools and private beaches to deluxe spas and wellness retreats so people can escape without an overnight stay. Our marketplace now connects guests with 2,500+ partner hotels and resorts, including Ritz-Carlton, Four Seasons, Marriott, Hilton, and more. We've helped millions of people enjoy premium hospitality close to home, making rest more mindful, togetherness more meaningful, and escape more accessible. The result: unforgettable experiences for guests and new revenue streams for partners. Backed by some of the best consumer and growth investors, including CRV, Declaration, Brian Kelly (The Points Guy), WME, FJ Labs, and more, ResortPass is scaling a product people love and creating an entirely new way to experience hospitality.

ABOUT THE ROLE

We're looking for someone who's deeply passionate about leveraging hospitality technology to redefine what it means to be a guest. As Chief of Staff, you'll report directly to the CEO and play a key role in helping the organization evolve from its current stage to the next phase of scale. You'll drive operational efficiency, streamline communication, and ensure alignment across teams to support our next phase of growth. The ideal candidate is a process-oriented, highly organized leader who can manage multiple priorities and execute initiatives alongside several executives with minimal guidance. You should be an exceptional communicator, comfortable balancing strategic thinking with hands‑on execution, and eager to collaborate across all departments to keep the organization moving forward efficiently and effectively. This role will be in person at our energetic NYC headquarters 5 days a week. The base salary for this role will range from $150,000 - $200,000 per year, commensurate with experience.

WHAT YOU'LL DO

Establish company‑wide metrics/KPIs to drive alignment and clear objectives. Own investor relations: maintain reporting cadence, communications, and community‑building with existing and prospective investors. Partner with executives to digitize/systematize processes, reducing manual work and improving scalability. Partner with the CEO to manage the P&L: support disciplined capital allocation and identify levers to increase profitability. Lead strategic initiatives that deepen product value for guests and hotel partners. Oversee strategic initiatives end‑to‑end from scoping through execution while guiding senior leadership. Build analytics and dashboards that provide real‑time visibility into day‑to‑day operations. Partner with HR/People on hiring plans and employee matters. Review, design, and implement organizational structure improvements to close skill and knowledge gaps. Serve as the point person for company‑wide inquiries; develop action plans and drive project management and communications. Support executive leadership with decision‑making, program management, and implementation. Plan and run executive meetings, off‑sites, and board meetings.

WHO YOU ARE

We encourage candidates to apply even if they don't have 100% of the below qualifications. We believe in a holistic approach when evaluating talent for our team and post new roles often, so even if this role isn't quite right, we want to meet you! 2+ years in an operator and/or strategy role working closely with executives/C‑suite. 6+ years total experience in one or more of: management consulting, investment banking, and/or business operations at a fast‑growing tech startup. High EQ with the ability to adapt communication styles; adept at building, maintaining, and nurturing relationships across executives and investors. Proven track record organizing and coordinating across multiple teams/departments. Strong project management experience working cross‑functionally. Experience with revenue operations and budget management. Proficient in data analysis. You're a good person. While building a startup is hard, being a good person is not. We're building a team you'd genuinely look forward to working with every day. While we offer incredible experiences to our guests, it is just as important to us to foster an incredible culture for our employees.

BENEFITS

Health, Dental & Vision — We're deeply invested in the health and well‑being of our team and are proud to contribute to the monthly premiums of these insurance plans. Stock Option Plan — We offer employees the opportunity to become part‑owners in our mission. Let's redefine what it means to be a guest, together. 401k plan — Save for your future with a 401k plan offering. Unlimited Paid Time Off (PTO) — Enjoy life away from work to be inspired and fully recharge with unlimited paid time off. Annual ResortPass credit — Our mission is to bring delight and relaxation to people around the world; including our employees! Access private beaches, deluxe saunas, awesome pools, and much more with your annual credit. Voluntary Self‑Identification For government reporting purposes, we ask candidates to respond to the below self‑identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file. As set forth in ResortPass’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law. If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

• Disabled veteran”: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service‑connected disability.
• Recently separated veteran”: meaning any veteran during the three‑year period beginning on the date of such veteran’s discharge or release from active duty in the U.S. military, ground, naval, or air service.
• Active duty wartime or campaign badge veteran”: a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.
• Armed forces service medal veteran”: a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

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