Controller (Vacation Rental Portfolio)

About Howard Financial

Howard Financial is a full-service back-office solution for companies and entities with bookkeeping, payroll, and bespoke reporting needs that require accuracy, timeliness, and institutional-quality reporting without the burden of full-time staff.

We are an experienced team of bookkeepers and administrators with multiple decades of combined experience across industries allowing companies to focus on their core business while we handle the rest.

Founded in 2023, our team of 60 professionals supports ~40 clients across a diverse range of industries. We recently reached $5M of contracted ARR and are growing rapidly (over 150% MRR growth YTD).

About The Role

We are seeking a highly skilled Controller to oversee the accounting and financial operations for Howard’s rapidly growing global portfolio of short-term vacation rentals. This role is responsible for building our accounting function from the ground up, implementing scalable processes, and ensuring world-class financial reporting for both the company and property owners.

This is a foundational hire. You will shape the accounting team, define the standards, and drive financial excellence across the organization.

Previous experience in short-term rentals, trust accounting, PMS systems, and owner statement reporting is mandatory.

This role is highly client-focused — accuracy, transparency, and communication are essential.

Key Responsibilities

Portfolio Accounting & Financial Management

Oversee full-cycle accounting for a large, multi-market portfolio of vacation rentals.

Manage all trust accounting functions, including escrow/trust reconciliation and compliance.

Deliver timely, accurate owner statements and reporting packages.

Ensure proper recognition of revenue, expenses, owner payouts, and reserves.

Systems & Process Leadership

Lead financial setup and integrations with Property Management Systems (PMS) such as Guesty, Hostaway, Streamline, etc.

Build scalable accounting workflows, SOPs, and reporting structures.

Identify and implement tools, automations, and best practices to improve efficiency.

Team Building & Leadership

Hire, mentor, and develop a high-performing accounting team as we expand.

Establish performance standards, quality controls, and review processes.

Client Communication & Support

Act as the financial point of contact for property owners and internal leadership.

Provide clear explanations of statements, adjustments, and financial activity.

Maintain a client-centric mindset, ensuring owners receive accurate and transparent reporting.

Compliance & Reporting

Oversee month-end close, reconciliations, and financial audits.

Maintain compliance with trust regulations, tax requirements, and internal policies.

Required Qualifications

Mandatory: Previous experience as a Controller or Senior Accountant in short-term vacation rentals, HOA, boutique hospitality, property management, or similar.

Direct experience with PMS systems (Guesty, Hostaway, Streamline, etc.).

Trust accounting knowledge and hands-on experience.

Proven track record producing owner statements and handling owner communications.

Experience managing a large rental or property portfolio.

Ability to build processes, systems, and teams from scratch.

Strong analytical skills and attention to detail.

Excellent communication skills — especially with clients and owners.

Comfort operating in a fast-growing, global, remote environment.

Preferred Qualifications

Experience operating across multiple states/countries.

Background in tech-enabled property management or hospitality SaaS integrations.

Prior team leadership experience.