Operational Bookkeeper

Extenteam is the AI-driven operations platform for short-term rental property management, headquartered in Miami and founded in 2021. Our platform, Shared Services, handles guest communication and daily operational workflows for 80,000+ properties by pairing an AI orchestration layer with a shared-services team of hospitality-trained specialists, so no guest inquiry goes unanswered, day or night, and no property manager has to staff for the 2am cancellation themselves.

We're industry-only: every workflow, integration, and agent we hire is built around property management specifically, not bolted on from a generalist platform. As we push more of that platform toward AI-led automation and self-serve tools, the software our own Shared Services team works in every day has to keep pace, that's this role.

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.

1. Financial Transactions:

• →Process weekly exit cleaning bills into Streamline and Spring Miller Property Management System and send reports to cleaners
• →Create ad hoc financial reports using Streamline and Spring Miller Property Management System 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 Streamline and Spring Miller Property Management System and send reports to maintenance personnel
• →Monitor input into Streamline and Spring Miller Property Management System for account and property accuracy
• →Process weekly arrival inspection transactions into Streamline and Spring Miller Property Management System
• →Bookkeeping tasks include entering receipts & invoices, creating & entering bills into Streamline and Spring Miller Property Management System, filing & organizing hard copy and digital files into Google Drive, and sending payments via Streamline online and Spring Miller Property Management System
• →Reconcile bank statements and ensure accuracy in financial records.
• →Process and submit sales tax for applicable states and 1099 preparation

2. Operational Support:

• →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

3. Vendor and Contractor Relations:

• →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

5. Compliance and Documentation:

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

6. Software Utilization:

• →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