Executive Assistant (with Bookkeeping Focus)

Somewhere; South Africa; Remote; ZAR 1,042,000 - 1,304,000; Full time

Job summary

A dynamic remote company is seeking an experienced Executive Assistant with a focus on bookkeeping to support the CEO across multiple businesses. The ideal candidate will possess strong organizational skills and bookkeeping experience. Key responsibilities include managing the CEO's calendar, overseeing bookkeeping tasks, and streamlining operations. This role offers growth opportunities into operations management or chief of staff as the company expands.

Qualifications

• 3-5+ years in an EA, Operations, Finance, Paralegal, or M&A-adjacent role.
• Strong bookkeeping and financial management experience, including setting up accounting systems.
• Able to manage multiple priorities across two distinct businesses.

Responsibilities

• Manage inbox: triage, prioritize, and draft concise replies.
• Oversee complex calendar management across time zones.
• Manage bookkeeping for both businesses (invoicing, bill pay, reconciliations).
• Assist with expense management and reconciliations.

Skills

Bookkeeping and financial management

Outstanding written and spoken English

Organizational skills

Judgment under ambiguity

Fast first-drafting ability

Tools

QuickBooks

Xero

Google Workspace

Microsoft 365

Job description

Overview

Job Title: Executive Assistant (with Bookkeeping Focus)

Type: Full-time, Independent Contractor

Location: Remote

Work hours: 9:00 AM - 5:00 PM US Pacific Time

About the Role

We are seeking a highly organized and digitally savvy Executive Assistant with strong bookkeeping and operations skills to support our CEO across two businesses: a high-growth startup and an established HVAC services company.

This is not a traditional EA role—you\'ll be a critical partner in managing the CEO\'s schedule, ensuring operational efficiency, and owning day-to-day financial processes until a formal finance function is established. You\'ll also provide lightweight support on legal and M&A workflows, helping streamline communication and coordination across multiple stakeholders.

The ideal candidate thrives in fast-paced, entrepreneurial environments, is confident making decisions with limited context, and can move first drafts from concept to something reviewable quickly.

Key Responsibilities

Executive Support

• Manage inbox: triage, prioritize, and draft concise replies.
• Own complex calendar management across time zones; schedule internal/external meetings.
• Coordinate travel logistics, itineraries, and accommodations.
• Track, process, and reconcile CEO and corporate expenses.
• Handle personal admin as needed to free the CEO for strategic priorities.

Bookkeeping & Financial Operations

• Manage bookkeeping for both businesses (invoicing, bill pay, reconciliations, and reporting).
• Set up and maintain accounting systems (QuickBooks, Xero).
• Collaborate with external accountants/advisors to ensure compliance and accuracy.
• Provide the CEO with regular financial updates and insights.

Operations & Workflow

• Create, improve, and document lightweight systems and checklists.
• Spin up structured first drafts (emails, memos, simple decks) and iterate quickly.
• Research vendors, tools, and solutions; present clear shortlists and recommendations.
• Track tasks and follow-ups to completion without hand-holding.
• Coordinate recurring company deadlines and ensure submissions are on time.

Finance, Legal & M&A Support (lightweight)

• Assist with expense management and reconciliations.
• Organize data rooms and diligence artifacts; maintain checklists for acquisitions.
• Coordinate with partner firms on document flow and signatures.
• Prepare simple slide materials and summaries for internal reviews.

Marketing & Communications

• Partner with the Marketing Director on CEO thought leadership and digital presence.
• Draft and refine communication materials such as presentations, emails, and posts.

Qualifications

• 3-5+ years in an EA, Operations, Finance, Paralegal, or M&A-adjacent role.
• Strong bookkeeping and financial management experience, including setting up accounting systems.
• Outstanding written and spoken English; crisp, professional communication.
• Highly organized with attention to detail and follow-through.
• Able to manage multiple priorities across two distinct businesses.
• Strong judgment under ambiguity; comfortable operating with limited context.
• Fast first-drafting ability: take a concept to a 30% draft quickly for review.

Nice to Have

• Paralegal training or hands-on experience with legal workflows.
• Exposure to buy-side diligence, data rooms, and checklists.
• Experience supporting executives who travel frequently across multiple time zones.

Tools You\'ll Use

• Google Workspace and Microsoft 365 (Docs, Sheets, Slides, Word, Excel).
• Slack and/or Microsoft Teams.
• WhatsApp for quick coordination.
• QuickBooks or Xero for bookkeeping.
• Asana, Notion, or ClickUp for task and project management.
• Basic familiarity with GitHub is a plus (not required).

What Great Looks Like

• CEO\'s calendar, inbox, and workflows run seamlessly.
• Books are accurate, up to date, and ready for review.
• Tasks and projects are proactively tracked through completion.
• First drafts of materials are clear, structured, and professional.
• Sensitive information is handled with the utmost confidentiality.
• Systems are created, documented, and continuously improved.

Growth Opportunities

As the businesses expand, this role can evolve into Operations Manager or Chief of Staff, with broader oversight of finance, legal, and cross-functional leadership.