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Squared Away logo
Squared Away

Military spouses who are your trusted assistants. We help CEOs, VCs, executives, and startup teams get their time back.

Chief Executive Assistant, Bookkeeping-Focused

BookkeeperBookkeeperContractRemoteLeadTeam 201-500Since 2018H1B No SponsorCompany SiteLinkedIn

Location

New York

Posted

107 days ago

Salary

$1.4K - $4K / month

Seniority

Lead

High SchoolEnglish

Job Description

Chief Executive Assistant, Bookkeeping-Focused

Squared Away

• 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

Job 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.

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