Executive Assistant

Executive Assistant Location: Alexandria, VA Title: Executive Assistant Reports to: Chief Executive Office Classification: Exempt (as a Full Time role). Why You’ll Love Working at RedPeg: Voted as one of The Washington Post’s Top Workplaces, we are an independent full service experiential marketing agency that connects brands to the consumers they need to reach through customized, personal engagement. Every day, we come together to create experiences that inspire extraordinary memories. With our main office in the Washington D.C metro area., we work with a roster of incredible brands including Capital One, Coca-Cola, Marriott Bonvoy, In&Out, Meta, Niantic, Nike, USAA and Virginia Lottery. We’re looking for highly personable, passionate, and innovative marketers to bring the true entrepreneur spirit, growth mindset, and independent thinking to our team! What This Role is About: This role is fast and full: 40-plus meetings a week, a lot of moving pieces, and no two days alike. You will run his calendar, inbox, travel, and meeting prep, and, just as much, help build his brand, manage his social, polish his decks, and stay close to the business development that drives growth, which is his number one focus. This is not a heads-down admin job. It is for someone detail-obsessed and highly organized who is also outgoing and confident, comfortable speaking directly to our CEO, pushing back when he’s wrong, and interrupting when something needs his attention now. You stay calm under pressure, keep everything confidential, and are fluent with the AI tools he uses every day. Key Responsibilities Own the CEO’s complex business and personal calendar across all of his ventures, 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 client and industry events, site visits, and meetings, with every detail aligned to the CEO’s schedule. Handle the physical-world logistics that come with the role: 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. Build, review, and finalize the CEO’s presentations and decks in both Keynote and PowerPoint, tightening the story, formatting, and layout so everything is clean, consistent, and client- or stage-ready. You do not need to be a creative; the job is making it polished and complete. Keep an eye on the brand and marketing the CEO touches, making sure anything that goes out under his name looks finished and on-brand, and partnering with the sales and marketing teams on growth materials. Actively manage the CEO’s social media presence, posting and engaging every few days to build his personal brand and keep it consistent with the company’s voice and marketing strategy. Understand where the business is headed and stay close to its most important business-development priorities, helping the CEO focus his time and follow-through on what moves growth forward. 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. What You’re All About: Roughly 6-8 years of experience across a blend of executive support, marketing, and business development. We are not looking for a single-lane specialist: the right person has done some EA work, some marketing, and some BD, and moves comfortably between supporting a leader, sharpening the brand, and thinking about growth. Multi-company exposure is a 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. A strong eye for presentations: able to build, update, polish, and finalize decks in both Keynote and PowerPoint that are clean, on-brand, and ready for clients or the stage, and comfortable helping deliver or pitch them when needed. Digital and social marketing are second nature to you. You are hands-on with the major platforms (LinkedIn, Instagram, X, TikTok, Facebook), understand how they work for a professional or executive brand, and are comfortable posting and engaging consistently on someone’s behalf. A marketing background helps a lot: time spent in or close to marketing, with a sense of how brand and messaging should look and feel. You do not need to be a designer, but you make things polished and complete. Comes with a sales and/or business-development background and understands how an agency or founder-led business wins and keeps clients. This role directly supports the CEO’s number one focus, which is growth. Experience with HubSpot or a comparable CRM. 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. 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. Available full-time and able to flex hours around the CEO’s schedule. Bachelor’s degree preferred. RedPeg PRIDE P ioneering Spirit – We don’t follow maps—we draw them. Bold ideas and new paths fueled by our independence R eal Connections – We value creatively driven experiences that connect brands and audiences in real and powerful ways. I nclusive Excellence – We foster a culture where every voice is heard, every perspective is valued, and everyone has the opportunity to thrive. D etail Obsessed – The work is in the craft. We obsess over every moment to make it flawless, meaningful, and unforgettable. E mbody One Team - No silos, no egos. Just passionate people working together to make the best work possible. 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. 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. RedPeg Marketing