We're looking for a Senior Bookkeeper to manage the books for approximately 10 related entities across a family holding company with interests in real estate, sports services, food retail, and private investments. You will work closely with the managing partner and outside accountants to keep every entity's records accurate, current, and reporting-ready.
This is a high-trust, high-ownership role. You will be the person who knows where every dollar is across a portfolio of related companies, keeps the intercompany activity clean, and makes sure the financial statements are ready when lenders and accountants need them. If you have multi-entity bookkeeping experience, are advanced in QuickBooks Online, and take genuine pride in keeping complex books without errors or delays, this role is a strong fit.
Why You'll Want to Join
- You will be paid in USD (bi-monthly: every 15th and 30th)
- Paid Time Off in accordance with company policy
- Observance of Holidays per company guidelines
- 100% remote setup so you can work wherever you're most productive
- This role requires availability during US business hours
- Work directly with the managing partner of a diversified family holding company with real operational complexity
- High-ownership bookkeeping role with direct visibility into a multi-entity investment portfolio
What You'll Work On
Day-to-Day Bookkeeping Across All Entities
- Manage invoices, accounts payable, and accounts receivable across approximately 10 related entities
- Record all transactions in QuickBooks Online and an internal portfolio dashboard including intercompany transactions between related companies
- Verify payables and prepare payments for the managing partner's final approval
- Process recurring bills including property taxes, loan payments, and vendor invoices
Month-End Close and Reconciliation
- Reconcile all bank, credit card, and loan accounts each month
- Complete the month-end close for every entity accurately and on time
- Bring the 2025 books current across all entities as a near-term priority
- Maintain schedules of loan balances and payments, and of intercompany balances across the portfolio
Investment and Owner Activity Tracking
- Record investment activity across the portfolio
- Track each owner's capital in and out of the companies accurately and completely
- Maintain clear records of what each entity owes and is owed
Financial Reporting
- Prepare weekly, monthly, and quarterly financial reports for each individual entity and on a combined basis
- Prepare the quarterly financial statements required by lenders
- Reconcile the internal dashboard to the books each quarter and resolve any discrepancies
Tax Support and Compliance
- Prepare year-end packages and 1099s to support the outside accountants during tax preparation
- Maintain organized records throughout the year so year-end is not a scramble
What You Bring
- 3 to 5 or more years of bookkeeping experience managing books for multiple related companies simultaneously
- Real estate bookkeeping experience strongly preferred, including rent, loans, and property expenses
- Advanced QuickBooks Online proficiency — this is the primary tool for this role
- Strong Excel or Google Sheets skills for financial schedules, reports, and reconciliations
- Comfortable learning new software tools including internal portfolio dashboards
- Detail-oriented with the ability to manage deadlines and competing priorities across many entities without dropping anything
- Discreet and trustworthy with confidential financial and family information
Nice to Have
- Experience bookkeeping for a family office, holding company, or investment portfolio
- Familiarity with intercompany accounting and consolidated reporting
- Background supporting outside accountants through tax preparation and audit processes
- Experience with loan tracking, capital account management, or real estate entity accounting
How to Apply
Please include:
- Your updated resume
- A short Loom video (1 to 2 minutes) introducing yourself, describing your multi-entity bookkeeping experience, and walking through how you manage the month-end close across multiple entities simultaneously
Only candidates who submit a Loom video will be moved to the next step of the hiring process.
If you are a detail-oriented bookkeeper who can keep complex, multi-entity books clean and current, handle intercompany activity accurately, and be the person the managing partner trusts to have the numbers right, this role gives you the ownership and the direct access to do your best work.
Application Process Overview
Our comprehensive selection process ensures we find the right fit for both you and our clients:
- Initial Application - Submit your application and complete our prequalifying questions
- Video Introduction - Record an video introduction to showcase your communication skills and work experience
- Role-Specific Assessment - Complete a homework assignment tailored to the position (if applicable)
- Recruitment Interview - Initial screening with our talent team
- Executive Interview - Meet with senior leadership to discuss role alignment
- Client Interview - Final interview with the client team you'd be supporting
- Background & Reference Check - Professional reference verification
- Job Offer - Successful candidates receive a formal offer to join the team
Each stage is designed to evaluate your fit for the role while giving you insights into our company culture and expectations.
We'll keep you informed throughout the process and provide feedback at each step.
