Operational Bookkeeper

Commitment to Excellence: Continuously raising the bar and setting new standards in guest communications and service delivery. 
Exceptional Collaboration: Thriving in a fast-paced, high-performance environment built on clear communication and teamwork. 
Unified Purpose: Aligning behind a shared mission to drive success with an intense focus. One shared consciousness. 
Data-Driven Decision-Making: Prioritizing data and results over emotions when making objective, professional decisions. 
Emphasis on Details: Details matter at every level. Leaders are expected to have a deep understanding of the specifics and adopt a hands-on management style.

Our company embraces a management style inspired by the ideals of "founder mode," as championed by Airbnb’s Brian Chesky. This means a hands-on, visionary approach to leadership, with a relentless focus on innovation, product excellence, and customer-centric decision-making. We encourage proactive problem-solving, direct involvement in key initiatives, and a collaborative, high-performance culture.

To learn more about the "founder mode" philosophy and how it shapes our operations, you can explore this link. Understanding this mindset will provide valuable context for how we operate and what we value in our team members. 

We are seeking a detail-oriented and experienced Operational Bookkeeper to join our team. As an Operational Bookkeeper, you will play a crucial role in managing financial transactions, ensuring accurate record-keeping, and supporting the overall operational efficiency of our vacation rental business. The ideal candidate will have a strong background in bookkeeping, excellent organizational skills, and the ability to thrive in a fast-paced environment.

• Process weekly exit cleaning bills into Quickbooks and send reports to cleaners
• Create ad hoc financial reports using Quickbooks and Excel/Sheets for various projects & requests for information by departments, vendors, and homeowners
• Export work orders from Breezeway operations software to process maintenance payments and add to property management software
• Process weekly work order transactions into Quickbooks and send reports to maintenance personnel
• Monitor input into Quickbooks for account and property accuracy
• Process weekly arrival inspection transactions into Quickbooks
• Bookkeeping tasks include entering receipts & invoices, creating & entering bills into Quickbooks, filing & organizing hard copy and digital files into Google Drive, and sending payments via Quickbooks online
• Reconcile bank statements and ensure accuracy in financial records

• Work closely with property managers, reservationists, and other operational teams to gather financial data and ensure consistency in reporting
• Provide financial insights to support operational decision-making

• Manage vendor and contractor payments, ensuring timely and accurate processing
• Maintain positive relationships with vendors and negotiate favorable terms when applicable
• Provide cross-department collaboration and overall logistical support through clear communication, organization, and critical thinking
• Aiding in fixing any billing or payment issues that arise with vendors
• Monitor the email for receipts from internal personnel
• Monitor pushed work orders from Breezeway operations software in property management software to be closed/charged to appropriate accounts
• Bill owners for items purchased from in-house inventory
• Assist in processing month-end financial statements for property owners
• Become familiar with the inventory of all homes, components, amenities, and experiences we offer in the area

• Ensure compliance with accounting principles, industry regulations, and internal policies
• Maintain organized and complete financial documentation for audits or reviews

• Utilize accounting software and property management systems to streamline financial processes
• Collaborate with IT or system administrators to optimize software functionalities

• Other tasks as needed

• Excellent written and verbal English skills. No exceptions. This position will be communicating via all mediums. 5 of 5 on our assessments
• Proven experience as a bookkeeper, preferably in the vacation rental or hospitality industry
• Proficiency in accounting software
• Strong understanding of financial principles and practices
• Excellent organizational and multitasking skills
• Attention to detail and accuracy in financial record-keeping
• Effective communication skills for collaboration with cross-functional teams
• Problem solving skills
• Ability to work independently
• Critical thinker
• Tech Savvy – Can learn technology and software quickly

• Vacation rental industry experience
• Common knowledge of the VR/STR industry

• Internet speed minimum 30mbps: Needs to be Wired (Buy a dongle if no LAN port)
• i5 11th Gen or higher
• Windows 11 / MacOS Catalina or higher
• Minimum of 8 GB RAM
• Private and quiet dedicated home office area (no roosters, dogs, children's noises in the background)
• Back-ups in case of power or internet provider interruptions
• Good headset and webcam (preferably noise-canceling headset)

• Competitive Salary — We offer a competitive salary that reflects the candidate’s experience, skills, and responsibilities.
• Remote Work — This role is 100% remote, allowing flexibility and eliminating daily commute.
• Paid Time Off — Standard leave entitlements (vacation, sick leave, vacation leave) for rest and well-being.
• HMO Coverage — Company-provided HMO plan, offering access to medical services via accredited hospitals and clinics under a Health Maintenance Organization. This helps ensure employees have access to routine checkups, consultations, and coverage for medical care.