Executive Personal Assistant

The Personal Executive Assistant provides high-level administrative, operational, logistical, and personal support to the Chief Executive Officer (“CEO”) and Executive Team. This role requires exceptional organization, discretion, professionalism, responsiveness, sound judgment, and the ability to manage multiple priorities in a fast-paced environment while effectively utilizing technology and available resources. The successful candidate will be highly organized, tech-savvy, and serve as a trusted support partner who anticipates needs, manages details, protects confidential information, and follows through on both business and personal responsibilities with accuracy, professionalism, and urgency. This position combines remote work with on-site office support, in-person meeting attendance, and occasional local travel. Most working hours will be performed remotely; however, on-site attendance is required for meetings, training, events, and other business needs. Company-provided equipment will be supplied as needed. Working hours are flexible; however, this position requires a high level of responsiveness, dependability, and timely follow-through throughout the workday. Responsibilities may occasionally require evening or weekend availability to support business or personal events and priorities. The position requires prolonged periods of sitting, frequent computer use, and occasional lifting or transporting of office supplies, food orders, packages, event materials, or similar items. Work Style The ideal candidate is exceptionally detail-oriented, proactive, dependable, resourceful, and comfortable managing both business and personal responsibilities with professionalism and discretion. This role is best suited for someone who enjoys helping others, thrives in a flexible and fast-paced environment, and can seamlessly transition between strategic executive support and day-to-day logistical responsibilities. The position offers significant flexibility, autonomy, and growth potential for the right individual and is intended to become a long-term, trusted partnership with the CEO. Key Responsibilities Read, review, organize, prioritize, and manage email communications on behalf of the CEO, with minimal direction. Screen phone calls, voicemails, mail, emails, inquiries, and other communications, responding directly or redirecting them as appropriate. Provide confidential administrative, logistical, and personal support for the CEO and family, including scheduling, purchasing, reservations, errands, coordination, and follow-through on time-sensitive matters communicated through email, phone, text message, Asana, or other communication platforms. Coordinate domestic and international travel arrangements, prepare detailed itineraries, review and categorize credit card transactions, complete expense and mileage reporting, and maintain accurate calendars. Manage multiple complex calendars by scheduling meetings, appointments, reminders, travel, events, and associated logistics while resolving scheduling conflicts proactively. Create, organize, maintain, and distribute agendas for weekly, monthly, quarterly, annual, all-staff, advisory board, and other meetings as needed. Attend required meetings and events in person, prepare meeting materials, coordinate refreshments and meals, take meeting notes, track action items, and distribute follow-up information. Coordinate, manage, and attend company and personal events, including events held at Trainz , the CEO’s home, and other locations, including the Company’s annual summer party and similar events. Create and manage guest lists, invitations, reminders, catering arrangements, vendor coordination, staffing, decorations, supplies, and all related event logistics. Coordinate all advisory board activities, including scheduling meetings, distributing materials before meetings, recording meeting minutes, tracking action items, and coordinating board payments and reimbursements following meetings. Review and manage company and personal mail delivered to the CEO’s residence during extended periods of absence, notifying the CEO of important matters and responding or redirecting communications when appropriate. Anticipate needs by identifying scheduling conflicts, logistical challenges, and operational issues before they occur and implementing effective solutions. Effectively navigate and utilize multiple web-based platforms for scheduling, coordination, research, purchasing, payment processing, communication, and project management. Perform special projects, administrative support activities, and other duties as assigned. Skills and Qualifications Education and Experience High school diploma or equivalent required. A minimum of three (3) years experience supporting a CEO, Owner, President, or other senior executives preferred.. Experience coordinating complex travel arrangements and itineraries required. Experience managing confidential personal and business matters required. Technical Skills Excellent written and verbal communication skills with the ability to identify and communicate information that is important for the CEO to know. High proficiency using the following business technology platforms: Google Chrome, Drive, Docs, Sheets, Slides, Chat, Forms Microsoft OneDrive, Word, Excel, PowerPoint, Power BI Asana Vimeo MileIQ RingCentral Evolving internal software systems Modern web-based technology applications Professional document formatting Ability to effectively organize and manage calendars, communications, meeting materials, agendas, travel itineraries, expenses, projects, and electronic files. Strong ability to quickly learn, master, and effectively teach new technology platforms and software applications. Professional Skills Demonstrates the highest level of integrity, discretion, and confidentiality when handling sensitive business and personal information. Exceptional organizational skills with outstanding attention to detail, accuracy, and follow-through. Strong interpersonal skills and a genuine desire to serve and support others. Excellent critical thinking, problem-solving, and resourcefulness with the ability to identify practical solutions independently. Exercises sound judgment and confidently makes decisions with minimal supervision. Maintains a positive, flexible, can-do attitude while managing a wide variety of responsibilities. Thrives in a non-bureaucratic, entrepreneurial, collaborative, and high-accountability environment. Dependable, responsive, adaptable, and capable of successfully managing constantly changing priorities. Demonstrates initiative by continuously seeking opportunities to improve processes, increase efficiency, and enhance executive support. Works collaboratively with all levels of the organization and willingly assists wherever needed. Additional Requirements Must possess reliable personal transportation for local travel and errands. Must possess and maintain a valid U.S. driver’s license. Must maintain a satisfactory Motor Vehicle Record as determined by Trainz’s insurance provider. Must successfully complete all required drug testing, including pre-employment, random, reasonable suspicion, post-accident or incident, return-to-duty, and follow-up testing as applicable. Must be legally authorized to work in the United States. Must successfully pass all required pre-employment screenings applicable to the position. #J-18808-Ljbffr