[Hiring] Chief of Staff @Assistantly

Role Description

As a Chief of Staff, you’ll operate as a strategic partner to the CEO, driving alignment across priorities, optimizing executive workflows, and ensuring seamless execution across teams. This role is designed to act as a true extension of the CEO—owning executive operations, driving structure and accountability, and ensuring seamless coordination across business and personal priorities.

• Lead key areas including executive workflow optimization, communication triage, multi-entity project coordination, and high-level logistics management.
• Own and optimize executive workflows, implementing scalable systems for inbox, calendar, and task management to improve efficiency and decision-making.
• Design and enforce operating cadences, delegation frameworks, and communication protocols to streamline collaboration across teams and entities.
• Manage full-access executive support, including inbox triage, calendar ownership, and prioritization of high-impact activities.
• Coordinate complex, multi-party travel logistics and events, ensuring seamless execution across shifting schedules and priorities.
• Act as the central point of coordination across multiple business entities, aligning priorities, tracking deliverables, and driving execution.
• Lead project management efforts for strategic initiatives, including estate planning, acquisitions, and operational improvements.
• Proactively identify operational gaps, bottlenecks, and inefficiencies, implementing solutions without requiring direction.
• Serve as a decision-routing hub, ensuring timely responses and appropriate escalation of critical matters.
• Maintain strict confidentiality and security across sensitive accounts, utilizing tools like password managers and secure access systems.
• Prepare reports, summaries, and updates to keep the CEO informed and positioned to make high-level decisions quickly.

Qualifications

• 5+ years of experience supporting a CEO, founder, or executive in a Chief of Staff or high-level Executive Assistant capacity.
• Proven experience building systems, workflows, and operational structures in fast-paced or high-growth environments.
• Exceptional organizational, prioritization, and decision-making skills with the ability to operate independently.
• Strong communication skills with the ability to manage stakeholders and drive alignment across teams.
• Experience managing complex travel logistics, executive communications, and cross-functional projects.
• High level of discretion and experience handling sensitive information and executive-level access.
• Comfortable working across multiple time zones and shifting priorities.
• Experience supporting founders with multiple entities, acquisitions, or scaling operations (preferred).

Requirements

• Productivity & Communication: Google Workspace, Slack, Zoom (must-have).
• Security & Access Management: LastPass, 1Password (must-have).
• Project Management: Notion, ClickUp, Asana, or similar (nice-to-have).
• Scheduling & Coordination: Google Calendar, travel booking platforms (must-have).

Benefits

• Competitive salary.
• Paid US holidays.
• Paid wellness days.
• Health & wellness allowance.
• Monthly profit sharing.
• Sales, AI, and Operations upskilling.
• Dedicated Success Manager and long-term placement support.