Executive Assistant to Chief Executive Officer

Caddy Moving is a fast-growing company in the moving and labor services space. They are seeking an Executive Assistant to the CEO who will manage the CEO's time and priorities, ensuring focus on high-impact activities and using AI tools to enhance productivity.

Responsibilities

• Own and manage the CEO's calendar—schedule, reschedule, protect time blocks, and ensure days are structured around high-impact priorities, not just whoever asked first
• Triage the CEO's inbox and communications—flag what's urgent, draft responses, and filter out the noise
• Track the CEO's goals, to-do list, and key initiatives—follow up on action items, flag things falling behind, and hold the CEO accountable to their own priorities
• Prep the CEO before meetings with agendas, context, and relevant materials, and capture action items afterward
• Serve as the first point of contact for internal and external stakeholders—employees, investors, partners, and customers
• Use AI tools to manage information overload: summarize documents, draft communications, research topics, organize data, and automate repetitive workflows
• Coordinate travel, events, and logistics as needed
• Handle confidential and sensitive information with discretion and sound judgment
• Anticipate needs before they're asked—the best gatekeepers solve problems the CEO doesn't even know they have yet

Skills

• 1–3 years as an executive assistant, operations coordinator, chief of staff, or similar role supporting senior leadership
• Moderate to advanced proficiency with AI tools—you actively use ChatGPT, Claude, or similar for writing, research, summarization, and workflow automation
• Exceptional organizational skills—you thrive in fast-paced, high-volume environments and nothing falls through the cracks
• Strong written and verbal communication skills to represent the CEO professionally to any audience
• High emotional intelligence and discretion—you'll be exposed to sensitive conversations involving employees, investors, and strategy
• Proactive, self-starter mentality—you don't wait to be told what needs to happen
• Comfort with ambiguity and shifting priorities—startup life means no two days look the same
• Familiarity with productivity tools (Google Workspace, Notion, Slack, Asana, or similar)
• Based in or willing to commute to Chicago, IL
• Experience supporting a founder or CEO at an early-stage or high-growth company
• Experience building AI-powered workflows for scheduling, email management, or task automation
• Background or interest in logistics, moving, or home services

Benefits

• Hybrid work model with flexibility and autonomy
• Direct access to the CEO and exposure to every part of the business
• A team that values speed, resourcefulness, and getting things done over titles and hierarchy
• Room to grow into a Chief of Staff or operations leadership role as the company scales

Company Overview