Chief of Staff

Job Description

About Assistantly

Assistantly connects exceptional Unicorn talent with fast-moving businesses where clarity, accountability, and high standards are non-negotiable—and where strong performance is genuinely supported.

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. From managing high-level initiatives to owning communication, decision flow, and cross-functional coordination, you’ll bring structure, clarity, and momentum to the business. You’ll be supported by structured systems, ongoing coaching, and a dedicated Success Manager to help you perform at your highest level.

This is a full-time, long-term opportunity designed for impact, leadership growth, and the ability to directly influence business performance, operations, and strategic outcomes.

About the Role

A leading medical transportation and healthcare logistics provider based in Northern California, is seeking a highly strategic, proactive, and systems-driven Chief of Staff to partner directly with the CEO across multiple business entities.

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. You will lead key areas including executive workflow optimization, communication triage, multi-entity project coordination, and high-level logistics management.

Requirements

• 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 independentlyStrong 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)
  

Tools You'll Use:

• 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