Chief of Staff to CEO

We’re a fast-growing holdings company that owns and operates multiple businesses across hospitality, restaurants, coffee, restoration services, logistics, and other service industries. We’re actively expanding through acquisitions and launching new ventures. We’re looking for a Chief of Staff to work directly with the CEO. This is not an Executive Assistant position. We’re looking for someone who enjoys solving complex problems, building systems, leading projects, and ensuring that important work actually gets done. You’ll be involved in nearly every part of the business and become a trusted partner to the CEO. If you’re someone who thrives in fast-paced environments, enjoys wearing multiple hats, and loves creating order out of chaos, we’d love to hear from you. ⸻ What You’ll Be Responsible For Executive Support * Partner directly with the CEO on strategic priorities * Help prioritize daily, weekly, and quarterly objectives * Prepare meeting agendas and follow-up action items * Manage high-priority projects and initiatives * Conduct research on acquisitions, vendors, software, and business opportunities Project Management * Own company-wide projects from planning through execution * Coordinate across multiple businesses and departments * Track deadlines and ensure projects stay on schedule * Remove roadblocks and keep teams moving * Hold team members accountable for commitments Operations * Improve operational systems and workflows * Build and document SOPs * Identify inefficiencies and recommend improvements * Assist with opening new locations and launching new businesses * Standardize processes across multiple companies Leadership Support * Attend leadership meetings and document action items * Track company KPIs and performance metrics * Prepare reports and executive dashboards * Ensure leadership teams follow through on priorities * Improve communication between departments Technology & AI * Manage and optimize ClickUp or other project management tools * Implement AI tools and automation where appropriate * Improve reporting, organization, and documentation * Help streamline repetitive processes ⸻ We’re Looking For Someone Who * Thinks like an owner * Takes initiative without waiting to be told what to do * Has exceptional organizational skills * Loves solving problems * Can manage multiple priorities simultaneously * Communicates clearly and professionally * Follows through relentlessly * Is comfortable giving updates and holding people accountable * Learns quickly and adapts to changing priorities ⸻ Qualifications * 3+ years in operations, project management, consulting, startups, or business leadership * Excellent written and verbal communication * Strong organizational and time management skills * Experience managing multiple projects at once * Comfortable working independently * Strong analytical and problem-solving abilities ⸻ Bonus Points * Startup or entrepreneurial experience * Multi-location business experience * Hospitality or restaurant experience * EOS (Entrepreneurial Operating System) * ClickUp, Asana, Monday.com, or Notion * AI workflow and automation experience * Financial reporting or KPI dashboard experience * M&A or acquisition experience ⸻ Success in This Role Within your first year, you’ll help: * Keep leadership aligned and accountable * Improve communication across multiple businesses * Build scalable systems and processes * Successfully execute high-impact projects * Free up significant CEO time by taking ownership of execution * Help prepare the company for continued growth and acquisitions ⸻ To Apply Please answer the following: 1. Tell us about the most complex project you’ve managed from start to finish. 2. Describe a process or system you created that significantly improved a business. 3. What project management software are you most experienced with? 4. Tell us about a time you had to keep senior leaders accountable to deadlines. 5. Why does this role interest you? We’re looking for someone who wants to grow into a long-term leadership position and help build an exceptional company—not someone looking for just another contract.