Remote Financial Chief Of Staff Job at Livesitter

About the Job

We are seeking a high-trust, high-ownership financial chief of staff to work directly with the owner across operating businesses and investment activity. This role has one mandate: Protect capital, eliminate waste, and improve decision-making through ruthless financial clarity. This is not a bookkeeping role. It is an execution-heavy, judgment-based role for someone who thinks like an owner, not an employee.

Key Responsibilities:

A. Cost reduction & financial discipline (Primary objective):
1. Conduct a line-by-line review of all expenses across entities
2. Identify and execute cost eliminations, reductions, or renegotiations
3. Continuously challenge recurring spend, subscriptions, and vendor creep
4. Build and maintain strict discretionary spending controls
5. Deliver bi-weekly expense reviews with clear recommendations
6. Success metric: Measurable monthly cost reduction

B. Financial systems & reporting:
1. Own QuickBooks online setup and structure across entities
2. Maintain clean class-based reporting (Primrose, livesitter, discretionary)
3. Ensure daily transaction accuracy and reconciliation
4. Produce timely and reliable: P&Ls, variance reports and cash flow snapshots
5. Maintain Qvinci sync and consolidated reporting
6. Success metric: Real-time financial visibility with zero surprises

C. Automation & controls:
1. Automate data ingestion from banks and credit cards
2. Implement alerts for: Spend anomalies, threshold breaches and month-over-month deviations
3. Design simple dashboards that surface issues without noise
4. Reduce manual work wherever possible
5. Success metric: Exceptions surface automatically, not manually

D. Banking, cards & account structure:
1. Rationalize bank and credit card accounts
2. Ensure clean separation between operating entities and discretionary spend
3. Map all payment methods correctly to accounting classes
4. Cancel unnecessary cards, accounts, and services
5. Success metric: Zero ambiguity about where money is going

E. Payroll, compliance & admin oversight:
1. Oversee payroll processing and W-2 issuance
2. Ensure records are audit-ready at all times
3. Coordinate with external accountants when needed
4. Handle daily bookkeeping and administrative finance tasks as required
5. Success metric: No compliance issues, no last-minute scrambles

F. Investment & due diligence support:
1. Assist with: Deal screening, financial modeling support and expense and ROI analysis
2. Document and data room management
3. Track deadlines, follow-ups, and open diligence items
4. Proactively surface opportunities and risks
5. Success metric: Faster, better investment decisions

Number of Openings

1 openings

Perks of this Jobs

5 days a week

Skills

Financial Reporting, Portfolio Management, Cost Control, Accounting, Investment Banking, Effective Communication, QuickBooks