Executive Personal Assistant to Founder

The Sterling Group is a modern psychotherapy practice for young adults in Washington, DC. We’re growing quickly and looking for a highly organized, proactive Executive Personal Assistant to directly support our Founder across multiple areas of business and life. This role is unique in that you would serve as the dedicated assistant to the owner of The Sterling Group — while also supporting the realities of a fast-moving entrepreneurial and family life. Our founder is not only leading multiple growing businesses, but is also a mom of two young children balancing leadership, operations, creativity, and family responsibilities simultaneously. This is not a traditional assistant role focused only on scheduling and inbox management. We’re looking for someone who thrives in fast-moving environments, enjoys bringing structure to chaos, anticipates needs before being asked, and can confidently manage many moving pieces at once. This role supports: • leadership and operations at The Sterling Group • a growing food and hospitality brand, Wake Upshur • and personal/family logistics and responsibilities The ideal candidate is exceptionally organized, detail-oriented, emotionally intelligent, tech-savvy, calm under pressure, and genuinely enjoys helping ambitious people operate more effectively. What You’ll Support: The Sterling Group (therapy practice) • Coordinate podcast appearances, speaking opportunities, and media logistics • Assist with event planning and team experiences • Help manage inboxes, scheduling, and follow-up communication • Support website audits and ongoing coordination with marketing/vendors • Assist with marketing tasks and organization • Help track projects, deadlines, and operational follow-through across the business • Coordinate meetings, interviews, travel, and scheduling logistics • Organize systems, documents, spreadsheets, and operational workflows • Assist with special projects and ongoing business initiatives Wake Upshur (small breakfast sandwich business) • Coordinate inventory and supply ordering • Help manage scheduling and market logistics • Communicate with vendors, organizers, and partners • Assist with operational organization and systems as the business grows • Support event coordination and ongoing administrative needs Personal & Family Support • Coordinate travel planning and reservations • Manage scheduling for children’s appointments and activities • Coordinate childcare logistics and calendar management • Order gifts, cards, groceries, and household supplies • Assist with restaurant reservations and personal errands • Coordinate online returns and household logistics • Help manage house repairs, vendors, and appointments • Maintain organized family calendars and ongoing to-do lists • Provide thoughtful day-to-day support that helps create more structure, bandwidth, and balance for a busy founder and parent Who You Are • Extremely organized and detail-oriented • Proactive and resourceful — you solve problems before they become problems • Excellent written and verbal communicator • Comfortable managing multiple priorities simultaneously • Calm under pressure and adaptable in fast-changing environments • Strong judgment and professionalism when handling sensitive information • Tech-savvy and quick to learn new systems • Able to “manage up” and keep projects moving forward • High ownership mentality — you don’t wait to be told every next step • Someone who genuinely enjoys creating calm, organization, and structure for others Preferred Experience: • Experience as an Executive Assistant, Operations Coordinator, Project Coordinator, Chief of Staff support, or similar role • Experience supporting founders, executives, entrepreneurs, or small business owners strongly preferred • Comfortable working across both professional and personal responsibilities • Experience with Google Workspace, spreadsheets, project management tools, scheduling systems, Canva, and general business technology platforms Details: • Full-time W2 position • Hybrid role based in Washington, DC • Combination of remote work, in-office support, and occasional local errands/logistics • Competitive compensation based on experience • Benefits package included This Role Is Probably a Great Fit If… • You love creating structure and organization • You’re the person everyone relies on to keep things running smoothly • You enjoy supporting ambitious, fast-moving founders • You’re energized by variety and problem-solving • You notice details other people miss • You genuinely enjoy helping people operate at a higher level • You like no two days looking exactly the same This Role Is Probably NOT a Good Fit If… • You prefer highly repetitive work with little ambiguity • You need constant direction or step-by-step instruction • You struggle with prioritization or fast-changing environments • You dislike juggling multiple projects and responsibilities simultaneously Pay: $25.00 - $30.00 per hour Benefits: • 401(k) matching • Dental insurance • Health insurance • Paid time off • Vision insurance Application Question(s): • How many years of experience do you have supporting executives, entrepreneurs, founders, or business owners? • This role involves frequent prioritization, follow-up, and shifting responsibilities. How comfortable are you working in a highly dynamic environment? • Are you comfortable supporting both business operations and personal/family logistics in a fast-paced environment? • What interests you most about this role? • Briefly describe your organizational style. Location: • Washington, DC 20005 (Preferred) Ability to Commute: • Washington, DC 20005 (Preferred) Work Location: Hybrid remote in Washington, DC 20005