Operational Bookkeeper

About Extenteam

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 Leadership Philosophy

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.

About the Role:

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.

Key Responsibilities:

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

Foundational Requirements:

• 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

Nice to haves:

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