Chief of Staff/Business Operations Manager (Real Estate, Legal & Multi Business Portfolio)

Long-Term Contract | Remote | Estimate. 40 hours/week We run a portfolio of growing businesses, spanning real estate brokerage, property management, personal injury legal operations, business education and events, and real estate development, and we are looking for a sharp, execution-focused Chief of Staff to work directly with the owner. This is not an admin role. You'll own projects, hold teams accountable, build systems, and help us scale. What You'll Do • Track and drive projects across all businesses from idea to completion • Conduct daily/weekly team check-ins and follow up on deliverables • Build and maintain SOPs and operational systems • Prepare weekly KPI and progress reports for leadership • Coordinate with bookkeepers, vendors, and legal/property teams • Monitor budgets, deadlines, and compliance items You're a Fit If You Have • 3+ years in operations, Chief of Staff, project management, or executive support • Experience working directly with business owners or executives • Exceptional organizational skills and strong follow-through • Bonus: QuickBooks, Buildium, Filevine, ClickUp, or Asana experience What Success Looks Like in 90 Days • Full visibility across all projects and departments • Improved team accountability and KPI tracking in place • Leadership spending more time on growth, less on fires To Apply Please include the following with your proposal: 1. A brief video intro (2–5 min) — walk us through your background, a system you've built, and why this role interests you 2. Answers to these screening questions: • What is the most complex operation you have managed? • What would your first 30 days look like? • Have you managed remote teams? If so, how many people? Hourly Rate: Open based on experience; please include your rate in your proposal. Applications without a proposal video and screening question answers will not be reviewed.