Executive Assistant & Bookkeeper

Executive Assistant & Bookkeeper
Remote — United States
Independent Contractor | Approximately 25 hours per week
$40,000 - 50,000 annual consulting fee paid weekly
An established small business is seeking an experienced executive assistant and bookkeeper to provide dependable administrative support to the CEO and Chief Operating Officer (COO), while maintaining accurate, current financial records.
This is an ongoing opportunity for someone who enjoys organizing priorities, keeping commitments on track, communicating professionally with clients, and managing day-to-day bookkeeping. We value sound judgment, accuracy, initiative, and consistent follow-through.
The business operates through one entity. Financial administration includes recurring client billing, credit card transactions, vendor payments, account reconciliation, and basic cash-flow forecasting.
What You Will DoExecutive and Administrative Support
Manage calendars in Microsoft Outlook for the CEO and COO, schedule meetings, coordinate participants, and resolve scheduling conflicts.
Assist both executives with Outlook email organization, routine correspondence, and tracking messages that require action.
Work with the CEO and COO to identify priorities and turn them into clear tasks and deadlines.
Maintain a shared, organized task list showing next steps, responsible parties, deadlines, and status.
Track responsibilities and follow up proactively on commitments involving either executive, clients, vendors, and other contacts.
Identify competing requests or scheduling conflicts and seek timely clarification on priorities.
Prepare a concise weekly update for both executives covering completed work, upcoming deadlines, pending decisions, and items needing attention.
Handle light client communication, including meeting coordination, routine correspondence, and requests for information.
Create and maintain Excel spreadsheets for tracking tasks, billing, expenses, and other business information.
Organize documents and maintain accessible, orderly electronic records.
Identify missing information or stalled tasks and take appropriate steps to move them forward.
Bookkeeping and Financial Administration
Maintain accurate records in QuickBooks.
Review and categorize bank and credit card transactions.
Collect and organize receipts, invoices, and supporting documentation.
Reconcile bank and credit card accounts monthly and investigate discrepancies.
Prepare and send client invoices according to monthly, quarterly, and annual billing schedules.
Track incoming payments, maintain accounts receivable records, and follow up professionally on overdue invoices.
Track vendor bills and due dates and prepare payments for approval.
Prepare routine QuickBooks reports, including profit and loss, balance sheet, and outstanding receivables and payables.
Use Excel to organize financial information, review exported reports, and prepare straightforward summaries.
Prepare and maintain a rolling 13-week cash-flow forecast in Excel using expected client collections, upcoming payables, recurring expenses, and other known cash commitments. Update weekly, compare actual results with projections, and flag potential cash shortfalls.
Keep financial records organized for the outside accountant and respond to requests for supporting information.
Flag unusual transactions, discrepancies, and accounting questions promptly.
Payment approval authority will remain with company leadership. Accounting matters requiring specialized judgment will be referred to the outside accountant or controller.
Initial Bookkeeping Catch-Up
The books are largely current through June. An initial project will involve reviewing the existing records, bringing subsequent months up to date, reconciling accounts, and identifying any unresolved items.
This catch-up work will be scoped and compensated separately from the ongoing engagement after a review of QuickBooks and the supporting records.
Experience and Qualifications
We are looking for someone who has:
Demonstrated experience providing executive or senior administrative support.
Experience supporting multiple executives and balancing competing priorities with clear communication and sound judgment.
Hands-on QuickBooks experience, including transaction categorization, invoicing, and bank and credit card reconciliation.
Proficiency in Microsoft Outlook, including email management, calendar management, meeting invitations, and scheduling.
Proficiency in Microsoft Excel, including creating and maintaining spreadsheets, sorting and filtering data, using common formulas, and preparing clear summaries.
Experience preparing basic cash-flow forecasts, including estimating the timing of customer receipts and outgoing payments.
A working understanding of accounts payable, accounts receivable, and routine financial reports.
A reliable method for managing priorities, deadlines, and follow-ups.
Strong written communication and a professional manner with clients and vendors.
Careful attention to detail and the judgment to recognize when something needs clarification.
The ability to work independently while keeping both executives informed.
Experience handling confidential business and financial information.
Reliable internet access, an appropriate computer, and a private workspace.
Professional references who can speak to accuracy, reliability, initiative, and follow-through.
Experience combining administrative support and bookkeeping in a small business is especially valuable. QuickBooks ProAdvisor certification is welcome but not required. A CPA designation is not required.
What Success Looks Like
Both executives’ calendars are coordinated and scheduling details are handled accurately.
Priorities, responsibilities, and next steps are clear.
Competing requests are surfaced promptly so priorities can be resolved.
Deadlines and outstanding requests are tracked and followed up.
Clients receive timely, professional communication.
Invoices go out on schedule and payments are tracked.
Financial records are current, documented, and reconciled.
Cash-flow forecasts provide a clear view of expected cash availability and potential shortfalls.
Spreadsheets and business records are accurate, organized, and easy to use.
Problems are raised early, with enough information to make a decision.
The CEO and COO can delegate work with confidence that it will be completed or brought back promptly for clarification.
Hours, Availability, and Compensation
Location: Remote, U.S.-based.
Engagement: Independent contractor consulting arrangement.
Expected commitment: Approximately 25 hours per week in total, covering support for both executives, bookkeeping, and cash-flow forecasting.
Compensation: Fixed annual consulting fee of $40,000-$50,000 based upon experience
Availability: Regular weekday availability with sufficient overlap during Eastern Time business hours for scheduling, communication, and follow-up. Specific response windows will be agreed upon.
Work allocation: Ongoing bookkeeping and cash-flow forecasting are initially estimated at approximately five hours per week, with the remaining time devoted to administrative and executive support. Actual needs will be reviewed during onboarding.
Scope: If ongoing needs consistently exceed 25 hours per week, scope and compensation will be reviewed together.
This is intended to be a continuing professional relationship. Independent consultants with other clients are welcome, provided they have the capacity and availability to meet the agreed commitments. As a consulting engagement, the fee does not include employee benefits.
How to Apply
Please submit:
Your résumé or a summary of relevant professional experience.
A brief description of a role in which you personally handled both administrative support and bookkeeping.
An example of how you managed competing priorities while supporting multiple executives.
Your experience with QuickBooks, including the reconciliations and financial reports you have prepared.
Examples of how you have used Outlook and Excel in previous work, including any cash-flow forecasting experience.
An explanation of how you track priorities and ensure outstanding tasks receive follow-up.
Your general weekday availability, time zone, and ability to commit approximately 25 hours per week.
Confirmation that the stated consulting fee meets your expectations.
Finalists will be invited to complete a short, paid practical exercise using sample administrative tasks and fictional bookkeeping and cash-flow information. Professional references will be requested before an engagement is offered.
Qualified applicants from all backgrounds are welcome. Selection will be based on relevant skills, experience, judgment, and demonstrated ability to perform the work.

Skills
Excel, Accounting, QuickBooks, Onboarding, Documentation

Work arrangement
Yes