Director of AI Integrations & Finance (Tampa)

We're hiring an individual to get the most out of our software and AI, connect our systems so they run themselves, and own our books and online marketing. This is not a typical back-office job. Most of your work will center on AI: mastering and integrating the software we already use, so our systems update automatically and guide our property managers exactly what to do and when. We'll also expect you to brainstorm new ways AI and their integrations can streamline operations that we haven't explored. The rest of your work covers finance, accounting and digital advertising, including quarterly financials, overseeing our bookkeeper, analysis of our securities portfolio, and optimizing our Google Ads and other online advertising.

Aware Investments is a small family office that owns, develops and operates commercial real estate across Central Florida. Our portfolio includes retail centers, office, industrial buildings, and hospitality. We also manage security portfolios.

We're small and move fast. You'll work directly with the principal, see the results of your work within weeks, and have real ownership of how we run.

1. AI, systems integration and operations (the core of the role)

• Learn our current software inside and out, including property management, accounting, Google Workspace and AI tools, and use the features we're not using yet.
• Connect our systems so data flows between them and updates automatically, without double entry.
• Set up our existing tools to give property managers a clear daily and weekly task list: what to do, for which tenant, and by when.
• Automate lease-driven reminders to tenants for rent, renewals, insurance certificates, CAM reconciliations and maintenance, timed to each lease's terms.
• Set up reporting that shows task completion, response times, work orders and occupancy across the portfolio.
• Use AI to track tenant and guest service: payment patterns, maintenance trends, reviews and feedback. Flag issues early.
• Make sure all employee and tenant monitoring complies with Florida and federal law, including call-recording consent and fair housing rules, and write the policies that go with it.
• Find new ways to use AI and automation across the business that we haven't thought of, and bring them to us with a clear payoff.
• Train staff, document every workflow, and measure the time saved.

2. Finance, accounting and investments

• Supervise our bookkeeper and review monthly closes across several entities.
• Prepare quarterly financials for each property and entity: income statements, balance sheets, cash flow and variance to budget.
• Run CAM and operating expense reconciliations, rent rolls, and AR aging.
• Build property budgets and cash flow forecasts, and support refinancing, acquisition and development analysis.
• Review our securities portfolio and build a tool that flags opportunities and makes recommendations based on the criteria we invest by.
• Work with our outside CPA, lenders, and insurance providers.

3. Digital advertising

• Optimize Google Ads campaigns for our available commercial space and hospitality properties.
• Manage our listings and ads on online platforms, social media, and commercial real estate listing sites.
• Track cost per lead and cost per booking, and report what's working.
• Manage outside freelancers or agencies when needed.
  

Required

• Proof that you've implemented AI or automation that people actually use, such as integrating software, automating workflows, or unlocking features a team wasn't using. Send examples: links, screenshots, or a short walkthrough video.
• Hands-on experience with large language models (Claude, ChatGPT or similar) and at least one automation platform (Zapier, Make, n8n, or Python scripts).
• 3+ years in accounting, finance or operations, ideally in real estate.
• Strong in Excel or Google Sheets, and comfortable with QuickBooks or similar accounting software.
• Able to read a commercial lease and explain the key terms.
• Bachelor's degree in accounting, finance, business, computer science, or a related field, or equivalent experience.
• Clear writer, self-starter, and comfortable working without a big team around you.

Preferred

• Experience with property management software such as AppFolio, Yardi, Buildium or RentManager.
• Has run Google Ads or Meta Ads campaigns with a measurable budget and results.
• Familiar with CAM reconciliations, NOI and cap rates, and loan covenant reporting.
• Some coding: Python, JavaScript, SQL, or APIs.
• CPA, CPA candidate, or real estate finance certification.
  

Pay: $90,000 per year, W-2, full-time, on-site at our Tampa office.

Benefits: Paid time off and all major holidays.