KeepingCount Director of Accounting - CPA Required Remote · Full time

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The KeepingCount group of companies provides accounting, bookkeeping, tax advisory, and CFO services to businesses in a variety of industry verticals such as real estate, life sciences, e-commerce, and more. We understand the uniqueness of these industries and work with our clients to help create the perfect scope to meet your needs. KeepingCount takes care of all financial and regulatory details so that you, the industry professional, can stay focused on your goals. Why Join Our Team? We know that you have many employment opportunities, however, few can match the unique and rewarding career that KeepingCount offers. We are committed to providing you the following: • Clear Career Development & Opportunity – We love to promote from within. • Culture, Comradery, & Community – We believe that work can and should be fun. • Mission-Driven Values, Meaningful Work – We truly believe in our core values – Conscientious, Gracious, and Discipline – they are what guide us as a company. • Work/Life Harmony – We are proud to offer flexible work schedules and a work from home opportunity. • Global Team Experience – We work closely with our international team members who all share our same passion for serving our clients in bookkeeping, accounting, and tax services.

Director of Accounting – Short-Term Rental

Position Overview

We are seeking an experienced Director of Accounting – Short-Term Rental to lead accounting operations and provide strategic financial oversight for our short-term rental (STR) clients. This role is responsible for ensuring accurate and timely financial reporting, maintaining strong accounting processes and controls, overseeing client engagements, and developing and leading accounting teams.

The ideal candidate is a CPA with strong technical accounting expertise, leadership experience, and a solid understanding of the unique accounting complexities within the short-term rental and hospitality industries. This individual will serve as a senior resource for both clients and internal teams and will play an important role in improving processes, strengthening client relationships, and supporting the continued growth of the business.

Key Responsibilities

Accounting & Financial Oversight

• Oversee accounting and financial reporting for a portfolio of short-term rental clients, ensuring accuracy, timeliness, and compliance with applicable accounting standards.
• Review monthly financial statements, balance sheets, income statements, cash flow reports, and supporting schedules.
• Ensure accurate account reconciliations, journal entries, accruals, and month-end and year-end close processes.
• Provide technical accounting guidance and resolve complex accounting issues.
• Establish and maintain appropriate accounting policies, procedures, internal controls, and documentation.
• Review financial results for accuracy, identify trends or discrepancies, and provide meaningful financial insights to clients and leadership.
• Partner with tax professionals and other advisors to support year-end reporting, tax preparation, and compliance requirements.

Short-Term Rental Industry Expertise

• Provide accounting leadership specific to the short-term rental and hospitality industries, including multi-property and multi-entity accounting environments.
• Oversee accounting related to rental revenue, management fees, owner distributions, security deposits, cleaning fees, occupancy taxes, sales and lodging taxes, and other property-level transactions.
• Ensure accurate reconciliation of property management systems, booking platforms, merchant processors, and bank activity.
• Support accounting for properties operating across multiple jurisdictions with varying tax and reporting requirements.
• Understand and address the financial complexities associated with property owners, property managers, booking channels, and third-party vendors.
• Identify opportunities to standardize and improve accounting processes across STR client portfolios.

Client Leadership

• Serve as a senior accounting advisor and trusted partner to clients.
• Lead financial review meetings and communicate complex accounting matters in a clear, practical manner.
• Develop a strong understanding of each client's operations, reporting needs, and financial objectives.
• Proactively identify accounting issues, operational risks, process gaps, and opportunities for improvement.
• Maintain strong client relationships and ensure a high level of service and responsiveness.
• Assist with client onboarding, transitions, system implementations, and process development as needed.

Team Leadership & Development

• Lead, mentor, and develop accounting managers, senior accountants, staff accountants, and other team members.
• Provide technical guidance, coaching, and ongoing performance feedback.
• Review team deliverables and ensure work meets established quality and accuracy standards.
• Establish clear expectations, priorities, and accountability across the team.
• Support staffing decisions, workload management, training, and professional development.
• Foster a collaborative, solutions-oriented, and client-focused team environment.

Process Improvement & Strategic Leadership

• Evaluate existing accounting workflows and implement scalable processes, controls, and best practices.
• Identify opportunities for automation and improved use of accounting and property management technology.
• Partner with senior leadership on operational initiatives, client strategy, staffing needs, and organizational growth.
• Develop and monitor key performance indicators related to accounting operations, client service, and team performance.
• Support the development and implementation of standardized accounting procedures across the organization.

Qualifications

Required

• Active Certified Public Accountant (CPA) license required.
• Bachelor's degree in Accounting, Finance, or a related field.
• 8+ years of progressive accounting experience, including significant experience in a leadership or management capacity.
• Strong knowledge of GAAP and financial reporting requirements.
• Experience overseeing month-end close, financial statement preparation, reconciliations, and complex accounting transactions.
• Demonstrated experience leading and developing accounting teams.
• Strong client-service and relationship-management skills.
• Excellent analytical, problem-solving, organizational, and communication skills.
• Ability to manage multiple clients, priorities, and deadlines in a fast-paced environment.
• Advanced proficiency with accounting systems and Microsoft Excel.

Strongly Preferred

• Experience working within the short-term rental, vacation rental, property management, hospitality, or real estate industries.
• Experience with multi-entity and/or multi-property accounting.
• Knowledge of short-term rental revenue recognition, owner statements and distributions, management fees, occupancy/lodging taxes, and property-level accounting.
• Experience working with property management systems and STR platforms such as Guesty, Streamline, Track, or similar systems.
• Experience with QuickBooks Online and related accounting technology.
• Experience in a client-service, outsourced accounting, advisory, or professional services environment.

What Success Looks Like

The Director of Accounting – Short-Term Rental will combine strong technical accounting knowledge with operational leadership and exceptional client service. Success in this role means delivering accurate and timely financial reporting, building strong accounting teams, creating scalable processes, proactively solving client challenges, and serving as a trusted financial leader for clients operating in the short-term rental industry.