Executive Assistant at Hudson Oaks

ABOUT THE ROLE We are seeking a sharp, proactive, and highly organized Executive Assistant to support a dynamic entrepreneur who owns and operates multiple businesses across real estate, professional services, and retail/e-commerce. This is not a traditional 9-to-5 role — it is a high-impact position for someone who thrives in a fast-moving environment, anticipates needs before they arise, and takes genuine ownership of their responsibilities. Your primary mission is simple: buy back the owner’s time. You will serve as a trusted right hand, handling everything from day-to-day administrative tasks to taking on meaningful projects that move the businesses forward. If you are energized by variety, love solving problems, and are proud of the way you execute, this role was built for you. CORE RESPONSIBILITIES Calendar & Email Management • Own and manage the owner’s calendar across multiple companies, proactively resolving conflicts and prioritizing time effectively • Serve as the first point of contact for all incoming communications — triaging, drafting responses, and escalating as appropriate • Ensure the owner is prepared for every meeting with relevant context, agendas, and materials in advance • Follow up on outstanding items and close communication loops without being asked Project & Task Execution • Take on ad-hoc projects across the business portfolio, from research and vendor coordination to operational support and special initiatives • Track open action items, deadlines, and deliverables across the organization and report status proactively • Identify inefficiencies and bring forward solutions before problems grow • Coordinate with team members, vendors, contractors, and external partners on the owner’s behalf Administrative & Operational Support • Manage travel planning, including itineraries, accommodations, and logistics for business and personal travel • Handle expense reporting, invoice processing, and light bookkeeping coordination with the accounting team • Maintain organized filing systems, contact databases, and shared resources • Support meeting facilitation, including note-taking and distribution of follow-up action items Cross-Business Coordination • Support real estate transaction coordination — helping track timelines, vendors, and key milestones across active deals • Assist with e-commerce and retail operations as needed — vendor follow-ups, order escalations, fulfillment coordination, or campaign support • Support professional services client communications and project tracking on behalf of the owner • Keep a pulse on priorities shifting across the portfolio and realign the owner’s attention accordingly • Handle sensitive and confidential information with discretion and professionalism at all times WHAT WE’RE LOOKING FOR • 3 years of experience as an Executive Assistant, Chief of Staff, or in a similar high-trust support role • Proven ability to manage multiple priorities simultaneously without dropping the ball — you are known for your follow-through • Exceptional written and verbal communication skills; you can represent the owner professionally in any setting • Strong proficiency with productivity tools: Google Workspace or Microsoft 365, calendar platforms, and project management tools (e.g., Asana, Notion, Monday.com) • High emotional intelligence — you read the room, adapt your approach, and build trust quickly • Comfortable with ambiguity; you can take a vague request and run with it, asking the right clarifying questions • Discretion is non-negotiable — you understand the sensitivity of the information you will be entrusted with • A self-starter mentality — you don’t wait to be told what needs to happen next WHAT MAKES YOU STAND OUT • Experience supporting a founder, entrepreneur, or executive who operates across multiple companies or ventures • Background that spans both administrative excellence and project management or operations • You’ve been told you’re “two steps ahead” — you anticipate needs, remove friction, and make things happen • You genuinely take pride in helping someone else be more effective THE ENVIRONMENT This role is in-office. The nature of the work requires close proximity and real-time responsiveness. You will be embedded in the day-to-day rhythm of the business, which means your schedule may flex based on what the owner and the businesses need. Flexibility is essential — some weeks will be straightforward, others will be intense. You are someone who embraces that reality. In return, you will have a front-row seat to how multiple businesses are built and operated. You will be trusted, challenged, and given the opportunity to grow well beyond a traditional support role. COMPENSATION & BENEFITS • Base salary: $55,000 – $70,000 depending on experience • Performance bonus eligibility • Paid time off and holidays • Opportunities for expanded responsibility and professional growth