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
Caddy is America's fastest growing moving labor company. It was founded in 2021, and is headquartered in Austin, Texas, US, with a workforce of 2-10 employees. Its website is .