Executive Assistant

Benefits: Bonus based on performance Flexible schedule Opportunity for advancement The Opportunity This is not a typical assistant role. You'll be working directly alongside a serial entrepreneur who currently leads four organizations, ranging from Employee Benefits to Mental Health Care businesses. He has started and sold multiple businesses and brings a wealth of real-world experience to everyone in his orbit. If you are detail-oriented, proactive, and thrive on bringing order to a fast-moving environment, this role offers something most entry-level jobs never can: genuine proximity to how businesses get built and run. What You'll Do Day-to-day tasks will vary, but expect a mix of: Opening and sorting mail; scanning and filing documents Depositing checks and handling routine bank runs Running errands (local, time-sensitive) Driving for the principal while he works in transit Updating spreadsheets, documents, and digital records Following up on outstanding tasks and tracking action items Light research and information gathering Supporting operational needs across multiple business contexts as they arise Who You Are Exceptionally detail-oriented — you catch what others miss Reliable and discreet — you handle sensitive business information with care A self-starter who can figure things out without handholding Comfortable moving between different business contexts in the same day Tech-capable: comfortable with Microsoft Office 365, basic document editing, and learning new tools Valid driver's license and clean driving record required Able to commit to a consistent weekly schedule What You'll Get $22–$28/hr depending on experience Flexible part-time hours (15–20/week) A front-row seat to multi-business entrepreneurship — operations, strategy, client relationships, and more Direct mentorship and exposure you simply cannot get in a classroom or a traditional job For the right person who grows into the role, expanded responsibilities and long-term stability Ideal Background No specific degree required. We care far more about your track record of follow-through than your credentials. Prior experience in administrative support, personal assistance, operations, or a fast-paced small business environment is a plus. To Apply Submit a brief cover note (no more than one page) telling us: One example of a time you managed multiple tasks or priorities without dropping the ball Why a long-term, part-time role like this, appeals to you right now Your availability and any scheduling constraints Applications without a cover note will not be reviewed. Flexible work from home options available.