Chief of Staff

Cruisebound is seeking a Chief of Staff to help shape the future of cruise booking. This is a high-impact, generalist role for an early-to-mid career operator who wants broad ownership across product, business development, and strategy at an early-stage startup. You’ll work closely with the COO as a true extension of their role, taking on delegated initiatives end-to-end and helping turn priorities into shipped outcomes.

This role is best suited for someone who operates well in ambiguity, writes clearly, thinks analytically, and wants to accelerate their trajectory through proximity, scope, and ownership rather than narrow specialization. Strong performers will have the opportunity to move into partnerships or product roles within 18-24 months.

This is a mostly-remote position based out of NYC to facilitate occasional coworking with the COO. Candidates must be NYC-based.

Your responsibilities

• Act as the COO’s shadow: prepare for meetings, capture decisions, and drive follow-ups with full context
• Own execution on delegated initiatives, managing timelines, dependencies, and risks with minimal oversight
• Draft, review, and pressure-test high-stakes docs, decks, specs, and exec or partner communications
• Turn raw inputs into clear, structured plans and artifacts
• Analyze data and build lightweight models or dashboards to support decisions and sanity-check assumptions
• Use LLM-based tools (Cursor, Claude Code, etc.) to vibe-code prototypes and internal tools; translate business intent into clear technical specs.
• Identify bottlenecks where leadership is constrained and proactively unblock, fix, or absorb them

Sample projects you might own

• Scope and pressure-test an expansion opportunity - new market, segment, or product line - and build the case for go/no-go.
• Rethink an internal tool or process as the business grows - run the POC and own implementation.
• Prepare materials and analysis for an exec or board-level decision: market sizing, vendor evaluation, org design proposal
• Run point on a major partner launch workstream - coordinating across product, eng, and the partner's team to hit a go-live date
• Diagnose a conversion or retention anomaly in the data, write up the findings, and drive the resulting fix to ship

The ideal candidate

• Has 3-5 years of experience owning execution in fast-paced, ambiguous environments (startup, consulting, ops, product, or similar)
• Has a bachelor's degree in a technical or analytical field, or equivalent practical experience
• Demonstrates strong judgment, clear written communication, and comfort working with data
• Balances attention to detail with an MVP mindset and bias toward action
• Is curious, proactive, and self-directed - does not wait to be told what to do
• Thrives in dynamic environments while staying humble, accountable, and adaptable

Compensation and benefits 

The compensation package for this position comprises: (1) a base salary ranging from $130,000 to $160,000 depending on the candidate’s experience, knowledge, and skills, and (2) an employee stock option grant. In addition, we also offer our employees a comprehensive range of benefits including but not limited to:

• $1,000 annual cruise credit to use on Cruisebound.com and additional employee rebates 
• Excellent health care insurance (medical, dental, vision, long-term disability, etc.)  
• Generous personal paid time off (PTO) allowance beginning with 20 days in the first year, plus 2 additional days per year of tenure (up to 30 days total) 
• 4 company-wide holidays (first Friday of each quarter) and 12 public holidays observed  
• $100/month communication credit intended for cell phone and Wi-Fi expenses 

About Cruisebound

Our mission is to help cruisers book their dream vacation by creating the best online booking experience for cruises.

We are customer centric - we focus on finding the fastest and most intuitive way to solve customer pain points. We are decisive - we don’t let perfect be the enemy of good. We are data driven - support every decision with data. We are one crew - we win and lose together, we are not afraid to make mistakes and learn from them.

Our founding team previously built and scaled Rocket Travel, a travel startup, to $900M in revenue.  Rocket is now part of Booking Holdings, the world leader in travel. We are a diverse team from around the globe who have learned about the travel industry at places like Booking.com, United Airlines, McKinsey, BCG, Stanford, and MIT.