Vacation Rental Onboarding Jobs (NOW HIRING)

About Aspen Vacations
Aspen Vacations is a luxury vacation rental company based in Aspen, CO, one of the world's most iconic destinations, managing a curated portfolio of exceptional properties across Aspen and Snowmass Village. True five-star hospitality is in the details: anticipating needs, personalizing every interaction, and creating unforgettable experiences from pre-arrival through post-departure. We are a close, collaborative team driven by a genuine commitment to our guests, our homeowners, and the standard of experience we deliver.
Position Summary
As the Accounting Manager, you will own all accounting, financial reporting, and compliance for Aspen Vacations, including vacation rental accounting across our managed portfolio of luxury properties. This is the senior finance seat in the company, working directly with the owner to support strategic decision-making.
The ideal candidate embraces technology and has a proven ability to leverage AI and automation to streamline workflows, improve accuracy, and drive efficiencies across the accounting department.
Responsibilities
Core Accounting
• Lead and manage day-to-day accounting operations, including the general ledger, accounts payable, accounts receivable, and journal entries.
• Complete month-end close on schedule, preparing timely and accurate financial statements and management reports, and maintain internal controls in compliance with GAAP and company accounting policies.
• Reconcile all bank, credit card, payment processor, and balance-sheet accounts monthly, ensuring proper segregation of operating, escrow, trust, and client funds.
• Ensure team members accurately document and code credit-card purchases to the correct property, owner, or department, following up on missing receipts and undocumented charges, and verifying that credits for returned items are received and posted.
• Ensure billing accuracy on all incoming and outgoing invoices, correcting discrepancies with a clear audit trail, and contacting vendors and merchants directly to resolve disputed charges, billing errors, and escalations.
Property Accounting
• Complete the monthly property accounting cycle, including reconciling OTA and direct reservation revenue and property-level expenses; filing and remitting state and local lodging and sales taxes; preparing and distributing owner statements; and processing owner payouts.
• Track and reconcile project expenses and prepare comprehensive, highly itemized owner invoices for property onboarding, updates, and improvement projects, ensuring all costs, fees, approved estimates, and supporting documentation are accurately reflected.
• Build strong, trusted relationships with property owners, promptly answering billing and statement questions and providing financial reports and supporting information upon request.
• Assist with new-property onboarding by collecting and organizing property and owner information, insurance certificates, owner payout details, W-9s, and vendor and utility account information, and accurately recording and maintaining this information across company systems and the CRM.
• Oversee reservation payment schedules and invoice accuracy; follow up on overdue or unsuccessful payments; assist in collecting amounts due for reservation modifications, additional services, and damages; process approved refunds; respond to chargebacks; and resolve guest billing questions.
Operations
• Maintain a compliance calendar to ensure all company insurance policies, business and sales-tax licenses, registrations, permits, and other required documents remain current and in good standing by completing renewals and filings on time.
• Manage applications and annual renewals for all short-term-rental licenses and permits across the portfolio, as well as other recurring property-specific registrations and subscriptions.
• Prepare and file Forms 1099-NEC and 1099-MISC accurately and on time.
• Prepare accurate year-end books and supporting schedules, and coordinate with the CPA on preparation and filing of tax returns.
• Administer employee onboarding paperwork, bi-weekly payroll, and employee benefits, and maintain accurate records of employee time off.
• Supervise and develop accounting support staff, and periodically train employees on proper purchasing and documentation procedures.
• Manage vendor and trade onboarding and maintain up-to-date files, including insurance certificates, business licenses, and W-9s; review invoices against approved estimates; and confirm completion and approval of work before processing payment.
• Work with leadership to improve financial visibility, develop budgets, and support strategic planning.
• Document and maintain clear procedures for recurring processes; identify gaps, inefficiencies, and control weaknesses; and implement practical workflow and system improvements and SOPs to strengthen accuracy, accountability, and timely execution.
• Partner with the owner on ad hoc financial projects, analysis, and special requests.
• Support the team cross-functionally as needed with guest communication and other administrative and office functions.
Requirements
• Bachelor's degree in Accounting, Finance, or a related field required; may be substituted with 10+ years of equivalent full-cycle accounting experience.
• 5+ years of full-cycle accounting experience, including independently managing month-end close, financial statement preparation, and account reconciliations.
• Experience in property management, vacation rental, hospitality, or real estate accounting strongly preferred, including trust or client fund accounting.
• In-depth understanding of Generally Accepted Accounting Principles (GAAP), with experience maintaining internal controls and ensuring compliance.
• Experience processing payroll and filing lodging, sales, and other state and local taxes.
• Experience leading an accounting function or serving as the primary accountant for a business, including supervising or training support staff.
• Proficient in QuickBooks and Microsoft Excel, and comfortable adapting to new technology, including property management and accounting software.
• Proven ability to leverage AI tools and automation to streamline accounting workflows and improve accuracy.
• Strong analytical, problem-solving, and process improvement skills.
• Impeccable attention to detail, accuracy, and organization, with disciplined record keeping.
• High level of integrity and discretion in handling confidential financial, payroll, and owner information.
• Excellent written and verbal communication skills, with a customer service focus, a team player approach, and the ability to explain financial information clearly to owners and team members.
• Thrives in a dynamic, fast-paced environment, with the ability to prioritize deadlines and switch gears without hesitation.
• Motivated to support exceptional experiences for guests and homeowners through accurate, reliable, and transparent accounting.
Benefits
• Salary range: $90,000 - $115,000 annually, commensurate with experience and qualifications.
• Health, dental, and vision insurance.
• Paid time off (PTO).
• Ski pass provided upon completion of the 90-day introductory period.
• Company phone provided.
• Opportunities for rapid growth within a dynamic, expanding company.
Schedule
Full-time, Monday through Friday, in-office.