Controller

Miami Beach, FL (or Miami-Dade/Broward, hybrid) W-2, 25–30 hrs/wk About DataStars DataStars is a real estate intelligence and advisory firm based in Miami Beach. We build data products that help lenders and investors see distress before it surfaces, and we advise institutional property owners on portfolio strategy. We are a small, senior team that uses modern tooling aggressively. The work is fast, the standards are high, and the deliverables go to people who make real decisions with them. The Role You will be the single financial operator across both practice areas. On the advisory side, you will manage deal-level accounting, fee tracking, and reconciliation with brokerage partners. On the intelligence side, you will handle subscription billing, per-engagement invoicing, and the books for a growing product business. Beyond the books, you will own the company's people-ops infrastructure. We need someone who has actually registered a retirement plan, set up Florida payroll, and navigated reemployment tax filings. Not someone who knows the theory. This role reports directly to the CEO. Financial Operations Maintain books across advisory and intelligence revenue streams Track and reconcile fee accruals against brokerage partner reporting Manage recurring subscription billing and variable per-engagement invoicing Prepare monthly financial summaries for the CEO Coordinate with external CPA on quarterly estimates and annual filings People Operations & Compliance Register and administer a 401(k) plan (Safe Harbor preferred) Set up and manage Florida payroll Handle Florida reemployment tax registration and quarterly filings Manage benefits administration, onboarding documentation, and I-9 compliance Maintain employee files and contractor agreements Deal-Level Support Track commission splits and fee waterfalls across multi-party advisory engagements Reconcile advance credits against earned fees Support escrow and closing accounting as transactions close Requirements 5+ years in accounting, controllership, or finance operations, with at least 2 years at a small or mid-size firm where you were the primary financial operator (not part of a large department) Direct experience registering and administering a small-company 401(k) or similar retirement plan Florida payroll experience: reemployment tax, new-hire reporting, workers' comp classification Proficiency in QuickBooks Online or Xero Working knowledge of W-2 vs. 1099 classification rules Ability to work independently without an accounting department around you Preferred Working familiarity with AI tools in a professional context. We use them daily and expect you to Experience in real estate, professional services, or SaaS company accounting Familiarity with brokerage commission structures or referral fee arrangements CPA designation or CPA-track What This Is Not This is not a bookkeeper role where you process transactions someone else categorized. You will design the chart of accounts, set the billing cadence, choose the payroll provider, and build the financial infrastructure from scratch. If you have only worked inside established systems, this will feel uncomfortable. If you have built the system yourself before, you know exactly what this is. #J-18808-Ljbffr