Executive Personal Assistant (EPA)

Job Overview We are seeking a highly organized, reliable, and proactive assistant to support a growth-focused entrepreneur who owns and operates multiple small businesses. This role is ideal for someone who thrives on structure, takes initiative, communicates clearly, and enjoys bringing order to fast-moving environments. You will help create routines, manage priorities, and keep both business and personal tasks running smoothly. Key Responsibilities Manage emails, mail, calendars, scheduling, and reminders Organize tasks, projects, and follow-ups across multiple businesses Draft and manage professional emails and communications Create and maintain simple systems, routines, and workflows Handle administrative tasks, research, and light bookkeeping support Anticipate needs, flag priorities, and take ownership of next steps Adapt quickly as new tasks and opportunities arise Helping with household tasks, such as scheduling landscapers and running errands Making travel arrangements, including researching, booking flights, car service and hotel rooms Ideal Candidate 3+ year experience as a Personal Assistant, Executive Assistant, or similar role Exceptionally organized with strong attention to detail Clear, concise, and professional communicator (written and verbal) Trustworthy, dependable, and comfortable handling confidential information Self-starter who takes initiative without constant direction Comfortable juggling multiple priorities and shifting timelines Tech-savvy (Mac-Based - Google Workspace, calendars, task tools, spreadsheets) Flexible mindset with a “figure it out” or "no job is too small" attitude Team player, able to communicate/collaborate with others This is an in-office position (Wilton) Best-Practice Attributes We Value Strong time-management and prioritization skills Ability to build and improve systems (not just follow them) Calm under pressure; solutions-oriented Good judgment and decision-making Comfortable working independently Growth-minded and open to feedback Why This Role Work directly with a driven entrepreneur Variety across personal & multiple businesses—no boring days Opportunity to grow responsibility and impact over time Flexible schedule with clear expectations Job Type: Part-time Pay: From $28.00 per hour Expected hours: 25 – 32 per week Work Location: In person