CHERRY ASSISTANT JOBS

Executive Assistant / Chief of Staff

Remote role for Cherry Assistant through Cherry Assistant.

FULL TIMEAmericas (North, Central, South America)40 hrs/weekR22,000 - R38,000

Job Description

What this role covers

We are hiring a Executive Assistant / Chief of Staff for a lean solo-consulting and startup-building company in the entrepreneurship and consulting industry. This is a full-time remote role for a US-based company.

This role is ideal for someone proactive, highly organized, assertive, and experienced in supporting fast-moving founders - someone who thrives in unstructured startup environments and can drive execution, manage systems, and provide strategic support across business and personal operations.

  • Project & Resource Management: Build and maintain centralized systems (ClickUp, Notion, Asana) to track tasks, projects, and resources. Ensure daily momentum through reporting, coordination, and follow-up.

  • Social Media Management: Lead LinkedIn and YouTube content strategy, including posting, graphics, audience engagement, analytics, and managing contractors. Translate strategic goals into content that drives brand growth.

  • Research & Business Support: Conduct business model research, mentor outreach, and product/offer brainstorming. Summarize courses and resources into actionable insights for founders.

  • Client & Administrative Support: Organize digital assets across Google Drive, OneDrive, and Zoho. Manage key documents, spreadsheets, and administrative tasks.

  • General Administrative Support: Oversee inboxes, calendars, bookkeeping, and daily executive operations.

  • Recruiting & Talent Sourcing: Support contractor lifecycle as needed — posting roles, screening, and coordinating interviews.

  • Personal Support: Manage travel, household vendors, events, and personal errands.

Required Qualifications:

  • 5+ years supporting founders, entrepreneurs, or business owners

  • Proven experience leading project and resource management systems (ClickUp, Notion, Asana)

  • Demonstrated ability to develop and execute social media strategies and manage content operations (LinkedIn, YouTube)

  • Experience conducting research, business analysis, and strategic planning to support founder decisions

  • Strong skills in digital organization and administrative systems across Google Drive, OneDrive, Zoho, and Microsoft Office

  • Ability to oversee executive operations, including calendars, inboxes, bookkeeping, and expenses

  • Exceptional written and spoken English and the ability to work independently

  • High attention to detail and execution quality

Preferred Qualifications:

  • Experience supporting consulting businesses or high-growth startups

  • Entrepreneurial or business ownership experience

Required Skills & Tools:

  • LinkedIn, Upwork, Fiverr

  • ClickUp, Notion, Asana

  • Canva

  • ChatGPT, Claude, Perplexity, Fathom

  • Gmail/Outlook, OneDrive/SharePoint, Zoho

  • Microsoft Office Suite

  • Instacart, Beehive (newsletter platform – preferred)

Schedule & Pay:

  • Full-time, remote 11 a.m. to 7 p.m. EST (U.S. Hours)

  • Pay: R22,000–R38,000/month depending on experience

  • Annual raises, performance bonuses, confirmed holiday PTO

System Requirements:

  • Internet ≥20 Mbps

  • Computer: 2.4 GHz+, 8 GB RAM

  • Windows 10+ or Mac OS X 10.10+

  • HD webcam, headset with microphone

Benefits:

  • Competitive pay

  • US phone number and business email

  • Fully remote, flexible work

  • Long-term collaboration and career growth

  • Stable hours and consistent pay

  • Supportive, high-performance environment

We are seeking an exceptional right-hand partner who thrives in dynamic environments, takes ownership without being asked, and consistently operates three steps ahead. Your impact will be immediate and meaningful.