Executive Assistant to Chief Executive Officer

About Caddy Moving

Caddy Moving is a fast-growing company in the moving and labor services space. We're scaling quickly—launching new products, managing a growing team, and serving an expanding base of customers and investors. We run lean, move fast, and use every tool available (especially AI) to stay ahead. We need someone who can operate the same way.

The Role

This isn't a traditional assistant role. We're hiring a gatekeeper for the CEO—someone who will take ownership of the CEO's time, inbox, priorities, and day-to-day rhythm so that more hours go toward the things that actually move the company forward. You'll be the filter between the CEO and everything competing for attention: employees, investors, customers, movers, vendors, and a growing list of product and operational priorities.

The right person for this role thinks like an operator, not just an organizer. You don't just manage a calendar—you look at the CEO's week and ask, "Is this actually where your time should be going?" You use AI tools to move faster, stay organized, and handle more than anyone would expect from a team of one.

What You'll Do

• 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

What We're Looking For

• 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

Bonus Points

• 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

What We Offer

• Competitive salary of $55,000–$60,000
• A front-row seat to how a fast-growing company is built—you'll learn more in this role than most people learn in five years
• 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