Accountant & Property Management

About the Role We are a private real estate investor with a growing portfolio of 11 long-term rental properties in Montana and a number of short-term rentals in the process of being acquired. We are looking for one skilled, dedicated person to take over the full bookkeeping function currently managed part-time, and also manage the day-to-day operations of our rental portfolio — both long-term and short-term — as we bring property management fully in-house. This is a combined accounting and property management role, and we need someone who is genuinely strong in both. On the accounting side, QuickBooks proficiency is non-negotiable — we need someone who can step in and run the books without extensive training. On the rental management side, we are willing to train the right person on our specific workflows, but we need someone smart and adaptable enough to learn quickly, manage vendors and tenants professionally, and figure things out without being walked through every step. Accounting & Bookkeeping This is the core technical requirement of the role. QuickBooks experience is required from day one. Daily Bookkeeping Manage day-to-day bookkeeping in QuickBooks Online, including transaction categorization, reconciliations, and data entry Maintain accurate and current financial records across all entities and properties Reconcile bank and credit card accounts on a regular basis to ensure books are clean and up to date Track rental income, security deposits, maintenance expenses, and property-level costs accurately Accounts Payable & Vendor Management Process and track vendor invoices and payments for maintenance, utilities, and property-related expenses Ensure all bills are paid on time and properly recorded in QuickBooks Maintain organized records of all vendor relationships, contracts, and payment history Reporting & Financial Oversight Generate and deliver regular financial reports — P&L by property, cash flow summaries, and owner reporting packages as needed Flag financial anomalies, unexpected expenses, or cash flow concerns to the owner proactively Long-Term Rental Management We are currently using a property management company for our 11 long-term rentals in Montana and intend to bring this fully in-house. We will train the right person on our specific processes, but we need someone who can quickly take ownership of the portfolio and manage it independently. Tenant Communication & Relations Serve as the primary point of contact for tenants across all 11 long-term rental properties Respond to tenant inquiries, maintenance requests, and concerns in a timely and professional manner Handle lease renewals, move-in and move-out coordination, and tenant onboarding Manage delinquent rent follow-up and maintain clear communication logs for all tenant interactions Maintenance Coordination Coordinate maintenance and repair requests by sourcing vendors, scheduling work, and following up on completion Maintain a list of trusted local vendors and contractors for routine and emergency property needs Review and approve vendor invoices for maintenance work before processing payment Conduct periodic property condition reviews and flag items needing attention Leasing & Vacancy Management Manage rental listings, screen applicants, and coordinate lease execution for vacant units Track lease expiration dates and initiate renewal conversations with tenants in advance Manage move-out processes including security deposit accounting and property turnover coordination Property Operations & Compliance Stay current on lease terms, rent amounts, and any property-specific requirements across all 11 units Maintain organized property files including leases, vendor records, maintenance logs, and tenant correspondence Coordinate with the owner on any issues requiring decisions, approvals, or budget exceptions Short-Term Rental Management We have short-term rental properties in Montana in the process of being acquired. We will work through the best workflow together during the transition period after closing. We intend to keep the short-term rental operation straightforward — primarily managed through Airbnb and VRBO directly. Platform Management Manage listings on Airbnb and VRBO — keeping availability calendars current, pricing updated, and listing content accurate Respond to guest inquiries and booking requests promptly and professionally Manage the guest communication cycle from booking confirmation through check-out and review Turnover & Cleaning Coordination Schedule and coordinate property turnovers and cleaning between guest stays Maintain relationships with local cleaning crews and ensure turnovers are completed on time and to standard Conduct or coordinate post-turnover checks and ensure the property is guest-ready before each arrival Guest Experience Provide guests with check-in instructions, house rules, and local recommendations in a welcoming and professional manner Handle guest issues, complaints, or special requests during their stay Monitor and respond to reviews to maintain strong ratings on both platforms Required Qualifications CPA and a strong QuickBooks Online proficiency — this is a hard requirement. Experience in full-cycle bookkeeping including reconciliations, AP, and financial reporting Highly organized with excellent attention to detail across both financial and operational responsibilities Strong written and verbal communication skills for tenant, guest, and vendor interactions Tech-savvy and capable of learning new software independently — whether property management platforms, Airbnb, VRBO, or other tools Self-directed and reliable — you own your responsibilities completely and the owner should not have to follow up on things you have been entrusted with Comfortable managing a remote property portfolio in Montana without being physically present Preferred Qualifications Prior experience in property management, real estate, or landlord support Experience managing short-term rental properties through Airbnb or VRBO Background supporting a private investor or small real estate portfolio directly Familiarity with property management software such as Buildium, AppFolio, or similar Experience transitioning a portfolio from a third-party management company to self-management This is a full time role Up to $10/hr 100% Remote