Chief of Staff & Executive Administrator

Chief of Staff & Executive Administrator

ABOUT SIMPLE FINANCIALS

Simple Financials is a growing bookkeeping, accounting, tax, and CFO advisory firm operated primarily by our outstanding team in the Philippines.
We help small business owners improve how they use QuickBooks Online and provide accurate financial reporting, analytics, and ongoing financial guidance. Our firm continues to grow through new clients, expanded services, strategic partnerships, and potential acquisitions.
We are hiring a Chief of Staff & Executive Administrator to help coordinate the company, strengthen our administrative systems, support our leadership team, and serve as a trusted partner to John, our Founder and CEO.
This is not a traditional executive assistant position. We are looking for an executive-level administrator and developing Chief of Staff who is also willing to perform detailed executive assistant work when needed.
The right person will be comfortable moving between companywide administration, accounting support, hiring, process development, meeting leadership, project coordination, and direct support for the Founder.

THE PURPOSE OF THIS ROLE

Simple Financials has grown to the point where important administrative and leadership responsibilities cannot remain concentrated with only the Founder and Director of Operations.
This person will help create greater accountability, organization, and redundancy throughout the company. They will make sure recurring responsibilities are completed, important projects continue moving, and leadership has accurate information when decisions need to be made.
At the same time, this person will take ownership of many of the responsibilities currently consuming the Founder’s time, including email , scheduling, meeting preparation, communication, and project follow-up.
Success in this role will allow the Founder to focus more of his time on:

• Acquiring other accounting firms
• Strategic partnerships
• Senior-level hiring
• Funding opportunities
• Business development
• New service offerings
• Long-term company strategy

PRIMARY RESPONSIBILITIES

Company Administration and Coordination

• Coordinate recurring administrative responsibilities across the company.
• Maintain PTO records, employee trackers, and administrative calendars.
• Review payroll information and timesheets for completeness and unusual activity.
• Assist employees with payroll and administrative onboarding matters.
• Confirm that background checks, employment documents, and security requirements are completed.
• Ensure tea ---------- mbers have proper systems access and two-factor authentication.
• Maintain organized records, checklists, and recurring administrative procedures.
• Identify responsibilities that currently depend on only one employee and establish backup coverage.
• Help leadership ensure important company obligations are completed accurately and on time.
• Facilitate internal meetings when other leadership tea ---------- mbers are unavailable.

Accounting, Billing, and Management Support

• Review recurring client billing for accuracy and completeness.
• Help confirm that client pricing matches approved proposals and current scopes of work.
• Monitor outstanding invoices and coordinate collection follow-up.
• Maintain client pricing and monthly billing information.
• Assist with quotes and proposals for prospective clients.

-Maintain management reports related to:

• Staff capacity
• Revenue by client
• Monthly billing
• Client profitability
• Staff profitability
• Staff utilization
• Accounts receivable
• Leadership scorecards
• Identify missing, unusual, or inconsistent financial information and follow up with the appropriate tea ---------- mber.
• Help leadership improve spreadsheets, dashboards, and recurring reporting systems.
• Provide administrative support for accounting projects without being responsible for all technical accounting work.

A strong understanding of accounting and QuickBooks Online is important because this role will regularly work with financial information, accountants, client billing, management reports, and accounting firm processes.

Hiring and Employee Onboarding

• Draft and update job descriptions.
• Coordinate interviews and communicate with candidates.
• Participate in interviews for selected positions.
• Maintain candidate notes, scorecards, and assessment results.
• Coordinate reference checks and background checks.
• Prepare onboarding schedules for new employees.
• Confirm that new hires receive the necessary accounts, equipment, documentation, and training.
• Help onboard new employees into payroll and company administrative systems.
• Follow up with managers to make sure onboarding responsibilities are completed.
• Help create a professional and consistent employee experience from recruiting through onboarding.

Processes, Quality Control, and Security

• Help write, organize, and maintain critical company processes.
• Turn rough notes, meeting transcripts, and recorded instructions into clear procedures.
• Coordinate quarterly quality assurance and quality control reviews.
• Track whether required QA/QC procedures have been completed.
• Identify missing processes, outdated documentation, and single points of failure.
• Maintain an organized company process library.
• Help ensure employees follow required privacy, security, and confidentiality procedures.
• Recommend improvements to recurring administrative and operational systems.

Leadership Meetings and Company Follow-Through

• Help organize leadership and all-hands meetings.
• Prepare agendas, scorecards, reports, and supporting documents.
• Gather department updates before meetings.
• Attend important company meetings and document decisions, assignments, and deadlines.
• Distribute action items and follow up with responsible tea ---------- mbers.
• Maintain a central list of major company projects and leadership commitments.
• Identify overdue or stalled projects and escalate them when necessary.
• Provide leadership with concise updates without requiring them to repeatedly request information.
• Help keep meetings focused, organized, and productive.

Executive Support for the Founder
A major part of this role will be creating leverage for John, the Founder and CEO.
Responsibilities will include:

• Reviewing and managing John’s email account throughout the workday.
• Routing email s and requests to the appropriate departments or tea ---------- mbers.
• Identifying urgent, sensitive, or time-sensitive matters requiring John’s attention.
• Drafting responses for email s John needs to answer.
• Responding directly to routine communications when authorized.
• Organizing, prioritizing, and maintaining the inbox.
• Tracking email s that require action or follow-up.
• Giving John short, organized summaries of matters requiring a decision.
• Managing John’s calendar and scheduling internal and external meetings.
• Protecting time for strategic projects and reducing unnecessary meetings.
• Preparing agendas, documents, and background information before meetings.
• Attending John’s important Simple Financials meetings.
• Tracking commitments and projects assigned by John.
• Following up with employees on projects where clients or tea ---------- mbers are depending on John.
• Helping manage John’s LinkedIn account and selected social media content.

The goal is for John to manage decisions and strategy rather than manage his inbox, calendar, and routine follow-up.

Strategic and Special Projects

• Support acquisitions, partnerships, software evaluations, and company growth projects.
• Conduct initial research and organize supporting information.
• Coordinate communication between internal and external participants.
• Track deadlines, decisions, and next steps.
• Prepare short summaries and decision documents.
• Help ensure projects continue moving when leadership attention shifts.
• Assist with light sales, marketing, recruiting, and business development activities.
• Represent the Founder in selected internal discussions after earning the necessary trust and authority.

WHO WE ARE LOOKING FOR

The ideal candidate combines accounting knowledge, administrative excellence, leadership potential, and executive judgment.
We will prioritize candidates who have:

• A degree or professional background in accounting.
• Significant experience using QuickBooks Online.
• Experience as an executive administrator, Chief of Staff, executive assistant, operations professional, or project coordinator.
• Excellent written and spoken English.
• Fast and dependable response times during working hours.
• Strong professional email communication.
• A polished and professional on-camera presence.
• Exceptional organization and follow-through.
• The ability to communicate confidently with employees, clients, and company leadership.
• The ability to respectfully hold others accountable.
• Sound judgment regarding what should be handled, delegated, escalated, or brought to the Founder’s attention.
• The ability to protect confidential financial, employee, client, and company information.
• A willingness to perform both strategic work and detailed administrative tasks.

A CPA credential is strongly preferred but is not required.
Candidates will complete a QuickBooks Online assessment so we can evaluate their current knowledge. Some QBO and accounting training can be provided, but candidates with strong existing accounting and QBO experience will receive priority.
Less-experienced candidates are also welcome to apply. We may consider promising applicants at a lower starting rate and provide additional paid training.

AI AND TECHNOLOGY REQUIREMENTS

The successful candidate must be an advanced and responsible user of AI and modern productivity tools, including:

• ChatGPT
• Claude
• Perplexity or comparable research tools
• QuickBooks Online
• Google Workspace or Microsoft 365
• Meeting transcription and summarization tools
• Project management and documentat