Sr. Accountant (Vacation Rental)

Howard; Región Metropolitana de Santiago; Remote; CLP 69,034,000 - 98,619,000; Full time

Benefits offered by this job

Remote work (USD compensation)

Growth into Controller-level scope

Direct access to leadership

Job summary

Howard Financial, a tech-forward outsourced accounting firm, seeks a Senior Accountant to own month-end close for vacation rental clients and oversee reconciliations and reporting at property and portfolio levels.

You will mentor staff, review work, and act as escalation point for accounting judgments while collaborating with the Controller to shape strategy for client accounts.

Qualifications

• 3-5+ years of progressive accounting experience, including senior level responsibilities.
• Hands-on experience in vacation rental, short-term rental, or property management accounting.
• Strong working knowledge of US GAAP and month-end close processes.
• Experience reconciling high-volume, multi-property data.
• Advanced Excel/Google Sheets skills.

Responsibilities

• Own full-cycle month-end close for vacation rental accounts, including journal entries and reconciliations.
• Reconcile owner statements, trust/escrow accounts, and revenue against PMS data.
• Mentor junior accounting staff and ensure accuracy before escalation.
• Prepare P&L and balance sheet analyses at property and portfolio levels.
• Manage AP/AR cycles and vendor/owner payments with tools like Ramp or Bill.com.
• Identify discrepancies in bookings, occupancy, and revenue data flowing to the general ledger.
• Assist budgeting, forecasting, and variance analysis for client portfolios.
• Document accounting procedures for vacation rental revenue cycles.
• Collaborate with Controller on account strategy and client communication.

Skills

US GAAP

Month-end close

Multi-property accounting

Excel/Sheets

English communication

Tools

Guesty

Streamline

Track

Hostaway

Ramp

Bill.com

Job description

About Howard Financial

Howard Financial is a tech-forward outsourced accounting and finance firm founded in 2023, delivering full-cycle accounting, controllership, and advisory services to clients across four verticals: Vacation Rental, Hospitality, Consumer & E-Commerce, and Development & Real Estate. We build lean, high-performing finance teams for our clients and pair them with modern tools and streamlined processes - no legacy bureaucracy, no bloated hierarchies.

ROLE PURPOSE

We're hiring a Senior Accountant to support one or more Vacation Rental clients, owning month-end close, reconciliations, and reporting for property-level and portfolio-level financials. This role sits above day-to-day bookkeeping and below Controller: you'll independently manage the close cycle, review the work of junior team members, and be the point of escalation for accounting judgment calls - while a Controller or Sr. Controller sets overall strategy for the account.

What You'll Do

• Own full-cycle month-end close for one or more Vacation Rental accounts, including journal entries, accruals, and account reconciliations.
• Reconcile owner statements, trust/escrow accounts, and property-level revenue against PMS data (e.g., Guesty, Streamline, Track, Hostaway).
• Review and mentor Bookkeepers/Accountants on the account, ensuring accuracy before work is escalated or finalized.
• Prepare and analyze financial statements (P&L, balance sheet) at the property and portfolio level for client and internal review.
• Manage AP/AR cycles as needed, including vendor and owner payment coordination through tools like Ramp or Bill.com.
• Identify and resolve discrepancies in booking, occupancy, and revenue data flowing from PMS into the general ledger.
• Support budgeting, forecasting, and variance analysis for client portfolios.
• Maintain and improve documentation of accounting procedures specific to the vacation rental revenue cycle (management fees, cleaning fees, owner payouts, channel commissions).
• Partner directly with the Controller/Sr. Controller on the account and communicate proactively with client-side stakeholders.

MUST-HAVES

• 3-5+ years of progressive accounting experience, including at least 1-2 years at a Senior Accountant level or equivalent scope.
• Hands-on experience in Vacation Rental, Short-Term Rental, or Property Management accounting - trust accounting exposure is strongly preferred.
• Solid working knowledge of US GAAP.
• Demonstrated ownership of full month-end close, not just transactional entry.
• Experience reconciling high-volume, multi-property transaction data (bookings, fees, owner disbursements).
• Strong Excel/Google Sheets skills (pivot tables, lookups, reconciliation workbooks).
• Comfortable working across multiple client accounts or entities simultaneously.
• Professional written and spoken English, given daily client-facing communication.

NICE-TO-HAVES

• Direct experience with Guesty, Streamline, Track, Hostaway, or similar vacation rental PMS platforms.
• Experience with Ramp, Bill.com, or QuickBooks Online.
• Background at a vacation rental operator, property manager, or outsourced accounting firm serving that space (e.g., Vacasa, Evolve, Sonder, Awning, Ximplifi, Accounting Prose, Verdant).
• Exposure to multi-entity or multi-client accounting environments.
• CPA in progress or completed (not required).

NOT A FIT IF

• Their experience is purely transactional bookkeeping with no ownership of close or reconciliations.
• They have no exposure to high-volume, multi-property or multi-entity data.
• They're looking for a purely back-office role with no client-facing communication.

What We Offer

• 100% remote work with a US-based, fast-growing firm.
• Exposure to multiple clients and business models within one of the most dynamic segments of hospitality.
• A flat, modern team structure - direct access to Controllers and leadership, no red tape.
• Competitive compensation in USD.
• Room to grow into Controller-level scope as the firm and your account expand.