Executive Assistant

• Own the CEO’s complex business and personal calendar across both companies, ensuring all appointments, meetings, and events are accurately scheduled and prioritized.
• Coordinate directly with counterparties and their assistants to schedule internal and external meetings, calls, and appointments in line with the CEO’s priorities and availability.
• Proactively identify and resolve scheduling conflicts before they reach the CEO, and protect focus time and travel buffers so recurring meetings do not decay.
• Serve as the single point of contact for scheduling inquiries, both internal and external, with prompt and professional responses.
• Triage the CEO’s inbox each morning, surfacing what matters and flagging time-sensitive items so he stays ahead of what needs his attention.
• Draft first-pass correspondence in the CEO’s voice for his review, and help ensure his daily briefings are accurate and complete.
• Prepare the CEO for meetings using prior notes and email threads, build detailed and accurate agendas, and take accurate minutes when requested.
• Track the commitments the CEO makes in meetings and drive the follow-through, including the calls and reminders that keep things moving.
• Act as the tactful “gatekeeper” among executives, employees, clients, and external partners, determining access to the CEO based on his priorities, projects, and schedule.
• Deflect what deserves deflecting and, when needed, say no gracefully on the CEO’s behalf.
• Keep the CEO informed of top priorities and upcoming commitments, following up appropriately.
• Book and manage all travel, including complex multi-stop trips around drone shows, industry events, board meetings, and site visits, with every detail aligned to the CEO’s schedule.
• Handle the physical-world logistics that come with travel and deal flow: signatures, notarizations, couriered documents, expenses, and reservations.
• Keep the CEO’s AI tools sharp: flag the emails that matter, mark commitments as done, keep his preferences and VIP contacts current, and tell us when the system is missing something.
• Collaborate with the sales and marketing teams to prepare impactful sales presentations and growth materials in both Keynote and PowerPoint, consistent with the company’s branding and goals.
• Assist in creating, scheduling, and managing the CEO’s marketing-related social media posts, keeping them consistent with the company’s branding and marketing strategy.
• Provide light personal support where business and personal life overlap: dinner reservations, personal appointments, occasional errands, and family scheduling as needed.
• Handle sensitive information, including personnel matters and confidential company and family details, with absolute discretion. A nondisclosure agreement is required.
• Be responsive to the CEO during business hours and, within reason, after hours and while he is traveling, with the flexibility to flex hours as the role grows.

• 5+ years supporting a founder, CEO, or similar senior principal, ideally with some personal-assistant experience. Multi-company or multi-entity experience is a strong plus.
• Genuinely comfortable working alongside AI tools every day and improving them, rather than competing with them. This is a real filter for the role.
• Calm, discreet, and direct, with demonstrated sound judgment and the confidence to make autonomous decisions with minimal supervision.
• Exceptional organization, time management, and attention to detail. Consistently early, dependable, and steady under pressure.
• Experience building sales and growth presentations in both Keynote and PowerPoint.
• Tech-savvy and proficient with the Microsoft suite (Outlook, Word, Excel) and comfortable on the Mac OS platform.
• Excellent written and verbal communication, with strong interpersonal skills across every level of an organization.
• Familiar with the major social platforms (LinkedIn, Facebook, Instagram, X, TikTok) and how they are used for a professional brand.
• Capable of handling confidential information with discretion and sensitivity at all times.
• DC-metro based with hybrid availability, and able to flex hours as needed.
• Open to starting part-time (approx. 20 hours/week) with a path to full-time as the role and the business grow.
• Bachelor’s degree preferred.

Next Steps:

To apply for this position please respond to this posting with your cover letter, resume and salary requirements. Only qualified applicants will be contacted.

It is the policy of RedPeg to provide equal employment opportunity (EEO) to all persons regardless of age, color, national origin, citizenship status, physical or mental disability, race, religion, creed, gender, sex, sexual orientation, gender identity and/or expression, genetic information, marital status, status with regard to public assistance, veteran status, or any other characteristic protected by federal, state or local law. In addition, RedPeg will provide reasonable accommodations for qualified individuals with disabilities.