Finance Operations Specialist

Cruisebound is on a mission to bring the joy of cruising to all travelers by making online booking as frictionless and simple as possible. We believe that in a world where you can do almost anything online, it shouldn’t be so hard to book the perfect cruise vacation.

If you are excited about using technology to drastically improve the way cruisers find and book their perfect vacation, Cruisebound is the right place for you. To apply, please include your resume and a brief cover letter explaining why you are interested in the position.

Cruisebound is looking for a sharp, curious Finance Operations Specialist to grow with us. This is not a traditional bookkeeping role. You'll be working at the intersection of finance and technology by owning our monthly commission reconciliation cycle, managing accounts receivables and payables workflows, and helping us systematically raise the bar on how we operate.

You'll report to the VP of Operations and work closely with our Operations, Data Science, and Supply teams, as well as with our external accounting partner, to administer and continuously improve our financial processes and systems.

Commission Reconciliation & Receivables

• Execute monthly commission reconciliation: import cruise line sailings data, upload and match cruise line payments, and reconcile expected vs. received commission by cruise line and booking
• Identify and investigate discrepancies (including cruise line errors, agent errors, product bugs, and commission recalls) and route findings to the appropriate owner
• Research and process chargebacks; maintain accurate records of outcomes and adjustments
• Track commission recalls and update receivables accordingly

Accounts Receivable & Payable

• Prepare and send invoices and follow up on outstanding payments
• Maintain receivables tracking for cruise line standard commission, cross-sell earnings (insurance, shore excursions, hotel), and bonus campaign earnings
• Administer monthly partner payout statements
• Support booking-level partner payout tracking to ensure accurate, timely payments

Month-End Close & Reporting

• Assist with month-end and year-end close in coordination with our external accounting partner
• Record financial transactions and maintain organized, accurate financial records
• Prepare and review monthly financial reports; flag discrepancies before books are closed
• Support external accountants during audits and tax preparation

Process & Tooling

• Operate and help improve internal tooling and data sync workflows for AR and AP
• Document SOPs as processes evolve actively identifying opportunities to reduce manual work through automation or AI tooling
• Work cross-functionally with external partners (including cruise lines, suppliers, financial partners, and brand partners) to resolve discrepancies and support reconciliation workflows

• 2–4 years of experience in bookkeeping, finance operations, or a related role
• Proficiency in QuickBooks (Online or Desktop)
• Strong Excel/Google Sheets skills
• Genuine enthusiasm for using AI and automation tools to reduce manual work. You don't need to know how to build them, but you need to want to use them.
• Strong attention to detail with an ability to investigate discrepancies methodically and communicate findings clearly.
• Ability to operate independently in an ambiguous, fast-moving environment 
• Excellent verbal and written communication skills.
• Comfortable working with technology, software systems, and web-based platforms.

• Familiarity with GAAP principles
• Familiarity with data tools like Holistics, Snowflake, or similar BI/data platforms.
• Exposure to reconciliation workflows involving third-party payment processors or remittance data.
• Experience working alongside an outsourced accounting partner.
• Experience in the travel industry (cruises, hotels, flights). 
• Experience at mid-stage tech startups.

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 - we 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 Schuylerville, Treungen, Waukesha, and Saguenay who have learned about the travel industry at places like Booking.com, United Airlines, McKinsey, and BCG. We are fortunate to be backed by Investors that include founders and leaders at Booking.com, SPG, TripAdvisor, Priceline, and Hotwire.