Assistant/Chauffeur to the CEO

ABOUT THE JOB

A busy CEO is seeking a dependable, proactive Assistant/Chauffeur to provide daily driving and hands-on executive support throughout the Washington metropolitan area.

Driving is at the center of this position. The CEO works primarily from a home office in Great Falls and travels regularly between Northern Virginia, the company's Rockville office, and Washington, DC. The Assistant will drive the CEO in a company vehicle, manage the vehicle and transportation logistics, and use the CEO's calendar to anticipate where she needs to be and when. Between trips and appointments, the Assistant will handle errands, follow up on assigned tasks, help with basic administrative needs, and step in where useful to keep the CEO's day moving. The role works closely with the CEO's Executive Assistant and Chief of Staff, with all three communicating throughout the day about schedules, priorities, deadlines, and upcoming needs.

The CEO has a structured, deadline-focused working style and communicates directly. She values people who are dependable, take initiative, learn quickly how to anticipate needs, and are comfortable managing themselves throughout the day.

Schedule

The workday will generally begin and end in Great Falls, VA, where the CEO maintains her home office. The exact daily schedule will follow the CEO's calendar and transportation needs, which is generally well-known in advance. Occasional extended days, regional travel, or evening/weekend coverage may be required and additional compensation will be provided.

THE EMPLOYER

The employer is the CEO of an established technology company specializing in health informatics, clinical research, and data solutions for government and healthcare organizations.

The CEO’s schedule is busy but structured, and she places a high value on deadlines, preparation, and follow-through. She is direct about what she expects and appreciates someone who is comfortable receiving feedback, making adjustments, and keeping her informed before something becomes a problem.

This role will become a trusted part of the CEO’s executive support team and will have visibility into her calendar, conversations, meetings, and business activities. Professional boundaries, sound judgment, and discretion are essential.

RESPONSIBILITIES

Driving & Transportation

• Safely and professionally drive the CEO to offices, meetings, appointments, events, and other destinations throughout Northern Virginia, Washington, DC, and Maryland
• Review the CEO's calendar and stay ahead of daily transportation needs, departure times, destinations, traffic, and schedule changes
• Plan routes in advance and maintain strong situational awareness while driving, without relying on a phone or navigation system in a way that creates distraction
• Maintain a clean, comfortable, and professional environment in the CEO's vehicle
• Coordinate routine maintenance, inspections, detailing, fuel, service appointments
• Keep the vehicle ready for use and proactively address maintenance or operational issues
• Maintain receipts and accurate records for vehicle and other authorized business expenses
• Prioritize safety, punctuality, discretion, and the CEO's comfort at all times

Executive Support

• Work closely with the Chief of Staff and Executive Assistant to coordinate the CEO's daily schedule, priorities, and logistical needs
• Maintain familiarity with the CEO's calendar and anticipate where support will be needed throughout the day
• Handle errands, pickups, deliveries, returns, purchases, and other assigned tasks between driving responsibilities
• Assist with straightforward administrative needs such as sending emails, updating calendar items, organizing documents, taking notes, or following up on assigned items
• Provide backup support when the Executive Assistant is unavailable or traveling, with support from the broader executive team
• Track assigned projects, tasks, and deadlines and provide clear updates on progress
• Participate in regular end-of-day status meetings with the CEO, Chief of Staff, and Executive Assistant to review outstanding items, deadlines, and upcoming priorities
• Assist with occasional company meetings or events as requested
• Provide limited support at the CEO's residence when needed, such as meeting a vendor or retrieving an item
• Become comfortable using the company's everyday technology and productivity tools

MUST HAVES

• Valid driver's license and good driving record
• Confident, safety-conscious driver who is comfortable navigating in the Greater DC area
• Exceptional dependability and punctuality
• Strong initiative and the ability to manage time independently throughout the day
• Ability to read a calendar, think ahead, and anticipate logistical needs rather than waiting for instructions
• Comfortable managing multiple priorities, deadlines, and changing requests
• Professional, polished presentation appropriate for a business environment
• Good understanding of confidentiality and professional boundaries
• Willingness to learn and use AI and other productivity tools as necessary
• Flexibility to accommodate occasional schedule changes, extended days, regional travel, and limited evening or weekend needs with advance notice

ABOUT YOU

• You are the person people can count on to be where you said you would be
• You notice what needs to happen next and take care of it without waiting to be asked
• You are assertive enough to manage your own day, follow up when necessary, and speak up before a deadline or logistical issue becomes a problem
• You communicate succinctly and know when an update is necessary and when it is not
• You are personable without being overly conversational and can develop a comfortable professional relationship while maintaining appropriate boundaries
• You take care with your appearance and understand that you are representing the CEO and company while working

COMPENSATION & BENEFITS

• $70,000 annual salary
• Medical, dental, and life insurance
• 401(k) with employer match
• Generous paid time off and holidays
• Tuition reimbursement, professional education and training opportunities
• Company-sponsored social events
• Additional compensation for qualifying extended travel/coverage