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Posted May 2, 2026

Executive Assistant

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<div class="benefits"> <div><strong>Benefits:</strong></div> <ul> <li>Bonus based on performance</li> <li>Flexible schedule</li> <li>Opportunity for advancement</li> </ul> </div> <div class="trix-content"> <div> <strong>The Opportunity<br></strong><br> </div><div>This is not a typical assistant role.<br><br> </div><div>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.<br><br> </div><div>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.<br><br> </div><div><br></div><div> <strong>What You'll Do<br></strong><br> </div><div>Day-to-day tasks will vary, but expect a mix of:<br><br> </div><ul> <li>Opening and sorting mail; scanning and filing documents</li> <li>Depositing checks and handling routine bank runs</li> <li>Running errands (local, time-sensitive)</li> <li>Driving for the principal while he works in transit</li> <li>Updating spreadsheets, documents, and digital records</li> <li>Following up on outstanding tasks and tracking action items</li> <li>Light research and information gathering</li> <li>Supporting operational needs across multiple business contexts as they arise</li> </ul><div><br></div><div> <strong>Who You Are<br></strong><br> </div><ul> <li>Exceptionally detail-oriented — you catch what others miss</li> <li>Reliable and discreet — you handle sensitive business information with care</li> <li>A self-starter who can figure things out without handholding</li> <li>Comfortable moving between different business contexts in the same day</li> <li>Tech-capable: comfortable with Microsoft Office 365, basic document editing, and learning new tools</li> <li>Valid driver's license and clean driving record required</li> <li>Able to commit to a consistent weekly schedule</li> </ul><div><br></div><div> <strong>What You'll Get<br></strong><br> </div><ul> <li>$22–$28/hr depending on experience</li> <li>Flexible part-time hours (15–20/week)</li> <li>A front-row seat to multi-business entrepreneurship — operations, strategy, client relationships, and more</li> <li>Direct mentorship and exposure you simply cannot get in a classroom or a traditional job</li> <li>For the right person who grows into the role, expanded responsibilities and long-term stability</li> </ul><div><br></div><div> <strong>Ideal Background<br></strong><br> </div><div>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.<br><br> </div><div><br></div><div> <strong>To Apply<br></strong><br> </div><div>Submit a brief cover note (no more than one page) telling us:<br><br> </div><ol> <li>One example of a time you managed multiple tasks or priorities without dropping the ball</li> <li>Why a long-term, part-time role like this, appeals to you right now</li> <li>Your availability and any scheduling constraints</li> </ol><div> <em>Applications without a cover note will not be reviewed.<br></em><br> </div><div> </div> </div> <p>Flexible work from home options available.</p>
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