
Chief Executive Assistant, Bookkeeping-Focused
Squared Away
contract
Posted on:
Location Type: Remote
Location: New York • United States
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Salary
💰 $1,440 - $4,000 per month
Job Level
About the role
- Manage and optimize complex executive calendars across time zones
- Anticipate conflicts and proactively resolve scheduling issues
- Protect executive focus by enforcing priorities and boundaries
- Manage executive inboxes with discretion and sound judgment
- Draft, respond to, and triage correspondence on behalf of executives
- Ensure urgent matters are surfaced promptly and appropriately
- Coordinate domestic and international travel end-to-end
- Prepare detailed itineraries and anticipate changes or disruptions
- Prepare meeting materials, agendas, presentations, and reports
- Track action items, deadlines, and follow-through across initiatives
- Create, document, and refine workflows to improve efficiency
- Identify tools and processes that reduce friction and increase clarity
- Conduct research on competitors, tools, vendors, and market trends
- Provide concise summaries to support executive decision-making
- Track and organize expenses, receipts, and financial records
- Assist with invoice tracking and follow-ups
- Support reconciliation of transactions and documentation
- Prepare basic financial summaries for executive review
- Handle sensitive and confidential information with absolute integrity
Requirements
- Administrative experience supporting senior leaders is required; experience supporting executive-level roles is strongly preferred.
- Must be based in a U.S. time zone (EST, CST, MST, or PST); applicants must reside in the United States, **excluding New York**
- **Must be available during normal business hours Monday–Friday, 9 AM–5 PM** (in your time zone) for regular client communication
- This role cannot be combined with another job that limits availability during these hours
- Ability to commit a minimum of **20 hours per week,** with flexibility to take on additional hours
- Experience working remotely is strongly preferred
- Reliable home office setup, including:
- - Mac or PC computer with webcam
- - High-speed internet
- - Smartphone with email capabilities
- - A designated, quiet workspace suitable for professional work
- Strong written and verbal communication skills, able to clearly and concisely communicate in a variety of contexts
- Proficiency in Microsoft Office, including Word, Excel, PowerPoint, and Outlook, with familiarity using project management tools
- Experience managing schedules, communication, and priorities across time zones
- Understanding of cross-cultural communication in a global working environment
- Exceptional organization and attention to detail
- High emotional intelligence and situational awareness
- Comfortable working independently without constant direction
- Tech-savvy and quick to learn new systems and tools
- Proactive mindset that anticipates needs rather than reacts
- Experience with QuickBooks, Xero, or similar tools
- Experience supporting bookkeeping or financial operations
- Strong comfort working with numbers and financial documentation
- High level of attention to detail and accuracy.
Benefits
- This is a contractor (1099) role with a revenue-sharing model.
- Assistants earn **60% of the monthly client plan value** for each client they support.
- Most assistants support 2–4 clients at a time, with each client on a different plan level.
- Because of this, earnings vary based on the mix of clients and plans an assistant chooses to take on and may fluctuate month to month.
- In practice, most assistants earn between **$1,440–$4,000 per month**, with opportunities to earn more based on client volume, plan levels, and tenure.
- Earnings may vary outside this range depending on client mix, with higher-tier or multiple clients increasing total earnings.
- Assistants have full control over how many clients they support, their workload, and their schedule.
- There is no minimum or maximum number of hours required, and earnings scale accordingly.
- Squared Away manages client acquisition, billing, and invoicing so you can focus on client work.
- You’ll have access to a vetted client base across industries including consulting, marketing, nonprofit, finance, real estate, and more.
- This is a fully remote role with flexibility in client load.
Applicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills & Tools
administrative experiencescheduling managementfinancial documentationbookkeepingMicrosoft OfficeQuickBooksXeroproject management toolsresearchworkflow optimization
Soft Skills
communication skillsorganizationattention to detailemotional intelligencesituational awarenessproactive mindsetindependenceflexibilitydiscretionjudgment