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.