Senior Executive Assistant at Cherry Assistant

• We are hiring a Senior Executive Assistant (Chief of Staff) for a boutique AI-first consulting company in the Professional Services (AI/Technology) industry. This is a Full-Time remote role for a Texas, USA based client. The role is focused on executive support, cross-functional coordination, business operations, and workflow optimization using AI. The ideal candidate is proactive, highly organized, AI-savvy, an exceptional communicator, and a systems thinker who thrives in fast-changing environments.

Key Responsibilities

• Own complex calendar management, inbox triage and prioritization across multiple time zones
• Serve as the communication hub between the executive and internal/external stakeholders, ensuring clear, timely follow-ups
• Coordinate domestic and international travel, itineraries, logistics, and rapid changes
• Drive meeting prep: agendas, briefings, note-taking, action tracking, and outcomes
• Build and refine SOPs, processes, and dashboards; implement AI-enabled workflows and automations
• Support Business Operations: project tracking, vendor coordination, light budgeting/expenses, and basic contract/admin tasks
• Support Marketing Operations: content calendars, asset coordination, basic publishing, and campaign logistics; maintain CRM hygiene
• Conduct research and produce concise summaries, briefs, and decision-ready recommendations
• Maintain tools/workspaces (project management, documentation, CRM) to keep information current and accessible
• Protect confidentiality and exercise impeccable judgment with sensitive information
• Coordinate event and conference logistics (scheduling, materials, follow-ups)
• Provide occasional personal admin support to maximize executive focus

Required Qualifications:

• 5+ years as an Executive Assistant, Senior EA, or Business Operations/Chief of Staff-type role supporting founders or senior executives
• Based in South Africa
• Experience in fast-paced consulting, professional services, or high-growth environments
• Proven mastery of calendar/inbox management and complex travel planning
• Exceptional written and verbal English communication; executive presence and discretion
• Demonstrated process building and project execution with minimal oversight; strong prioritization skills

Preferred Qualifications:

• Experience partnering with US-based executives and supporting Central Time working hours
• Hands-on Marketing Operations or Business Operations exposure (e.g., content calendars, CRM updates, campaign coordination)
• Project management training or certification (e.g., PMP, Scrum) and/or experience leading cross-functional initiatives
• Practical experience implementing AI tools (LLMs, research copilots) and workflow automation

Required Skills & Tools:

• Google Workspace (Gmail, Calendar, Drive, Docs/Sheets)
• Slack, Zoom, and scheduling tools (e.g., Calendly)
• Project management platforms (Asana, ClickUp, or Trello)
• Knowledge bases and documentation tools (Notion or Coda)
• CRM systems (HubSpot or Pipedrive)
• AI tools (e.g., ChatGPT, Perplexity, Claude) and automation platforms (Zapier or Make)

Schedule & Pay:

• Full-Time position; 9:00 AM – 5:00 PM Central Time (CT), Monday–Friday
• Fully remote role for a Texas, USA based client
• Pay ranges from R20,000-R40,000 per month
• Includes training on AI workflows, growth potential, and long-term engagement opportunities