An Executive Assistant provides skilled administrative support for a company executive or professional staff at an organization. Schedules meetings, calls and travel, manages correspondence, handles outside information requests and staff communications; may assist with preparing presentations.
$25-$27/hr, based on experience ($52K-$56K/yr) — with a performance review and raise at 90 days Reports to: Founder/Owner About Us Gratitude Property Holding LLC is a growing South Florida real estate company founded by former NFL linebacker and entrepreneur Stephen Tulloch. Stephen also owns Circle House Coffee, a community-driven coffee brand with two Fort Lauderdale locations and a growing product line, and is currently developing a new laundromat venture. We're building out systems including AI tools to run all of this more efficiently, and we need a right hand who can help lead that charge. The Role We're looking for a sharp, self-directed Operations & Executive Assistant to help organize and manage a fast-moving, multi-business portfolio. This is not a sit-and-wait-for-instructions role we need someone who shows up, thinks ahead, and brings ideas to the table. You'll work directly with the owner across real estate operations, the coffee shop, and new ventures, with real room to grow as the businesses expand. What You'll Do Manage the owner's calendar, communications, and daily priorities across all businesses Track leases, rent collection, maintenance requests, and vendor relationships across the property portfolio Coordinate with contractors, property managers, and tenants Help organize financial documents, receipts, and reporting for the accountant/bookkeeper Support the coffee shop with light admin (scheduling, ordering, vendor coordination) as needed Assist with research and setup for the new laundromat launch Help research, test, and roll out AI tools/agents to automate parts of the business Keep projects, deadlines, and priorities organized across everything you're the connective tissue Proactively flag problems and suggest solutions before being asked Who You Are Highly organized with strong follow-through things don't fall through the cracks on your watch A self-starter who takes initiative rather than waiting to be told what to do Comfortable wearing multiple hats and switching between real estate, retail, and admin tasks Tech-comfortable and curious willing to learn new tools and workflows, including AI-based ones Discreet and trustworthy with sensitive business and financial information Reliable shows up on time, every time Based in or near Fort Lauderdale, able to work in person Nice to Have (Not Required) Experience in real estate, property management, or hospitality/retail Prior experience as an executive/personal assistant Interest in entrepreneurship this is a great seat for someone who wants to learn how a small portfolio of businesses is actually run Compensation & Growth $25-$27/hr to start, based on experience, with a 90-day performance review Real path to increased responsibility (and pay) as the portfolio and AI systems scale Direct mentorship from the owner on real estate, small business, and brand-building
To Apply:
Send a resume and a short note on why you'd be a fit to Stephen@gratitude55.com. Tell us about a time you used AI or built a system to streamline records, operations, or a process that was previously disorganized.
