Bookkeeper & Finance Operations Specialist — QuickBooks Online

FULL-TIME BOOKKEEPER & FINANCE OPERATIONS SPECIALIST
Remote | Multi-Entity | AI-Assisted | Direct Hire

About Us
From Military to Millionaire helps service members and veterans build financial freedom through real estate, entrepreneurship, and financial literacy. We are a veteran-led education and community business with 1,300+ members and related real estate businesses.

Our core values are Trustworthy, Connected, Creative, Show Don’t Tell, and People Over Money.

About the Role
We’re looking for an experienced bookkeeper to maintain accurate, current books for our education business and related real estate companies.

You’ll work with QuickBooks Online and Claude, our AI assistant, to categorize transactions, reconcile accounts, calculate commissions, and prepare reports. You are responsible for checking AI output and ensuring every number is accurate.

This is a bookkeeping and finance operations role. Financial strategy stays with leadership, and tax preparation and advice stay with our CPA.

Responsibilities
Daily:

• Categorize bank, credit card, PayPal, Whop, and Stripe transactions in QuickBooks Online.
• Record new sales in our commission tracker and verify customers and cash received.
• Track payment plans and confirm required recurring subscriptions are active.
• Flag unusual transactions, duplicate charges, failed payments, or suspected fraud promptly.

Weekly:

• Prepare a one-page cash report covering account balances, collections, outstanding payment plans, and upcoming bills.
• Prepare bill and contractor payment batches for CEO approval and release.
• Update financial metrics on our company scorecard.

Monthly:

• Reconcile all bank, credit card, PayPal, and payment-processor clearing accounts to a $0 difference by business day 5.
• Reconcile intercompany balances.
• Deliver cash-basis Profit & Loss statements and Balance Sheets for each entity by business day 10, with a short explanation of changes.
• Calculate sales commissions on net cash collected after refunds, ready for CEO review by the 3rd.
• Verify annual-to-monthly membership billing transitions.
• Update revenue, CAC, LTV, churn, and ROAS metrics with AI assistance.

Ongoing:

• Prepare quarterly and year-end financial packages for our CPA.
• Collect contractor W-9s and prepare 1099 filing data.
• Document recurring processes with clear instructions and screenshots.
• Maintain and improve AI instructions and reporting templates.

You will prepare payments; the CEO approves and releases them.

Required Qualifications

• At least 3 years of hands-on bookkeeping experience for US businesses using QuickBooks Online.
• QuickBooks Online ProAdvisor certification. Include a link to your certificate.
• Strong accounting fundamentals, including reconciliations, month-end close, debits and credits, and cash versus accrual accounting.
• Experience maintaining books for multiple related entities and recording intercompany transactions.
• Strong Excel or Google Sheets skills, including lookups, pivot tables, and cleaning exports.
• Clear written and spoken English, including occasional calls with vendors or payment processors.
• Strong integrity, discretion, attention to detail, and ownership of deadlines.
• Comfortable using AI tools or willing to learn—and committed to independently checking their output.

Preferred Experience

• Real estate bookkeeping, rental properties, hospitality, or property manager reports.
• Sales commissions and payment plans.
• Whop, Stripe, GoHighLevel, Wise, Digits, or similar platforms.
• Accounting degree or CPA qualification.

Compensation and Schedule

• $1,400 - $1,800 USD per month, based on experience.
• 40 hours per week.
• At least 4 hours of overlap with US Central Time on weekdays.
• Flexible/unlimited PTO.
• Remote direct hire, with no agency fees.
• Company-provided Claude Team seat.

How to Apply
Send your application through OnlineJobs.ph using this subject:
Bad Ass Bookkeeper — [Your Name]
Include:
1. Your résumé.
2. A link to your QuickBooks Online ProAdvisor certificate.
3. Your results from this free DISC assessment: ----------
4. Three professional references, including their relationship to you.
5. A short answer to: “Tell us about a time you found an error in the books that everyone else had missed. How did you find it?”
6. Your expected monthly salary, earliest start date, and available working hours in US Central Time.
7. Put the word “RECONCILED” in your subject line after your name so we know you read to the end.

Please complete all application steps to be considered.