Cannonball Moments is a leadership development, executive coaching, speaking, and personal growth company built around a simple belief: people are capable of more. Our work is about helping people become better leaders, better teammates, better partners, and better versions of themselves. We care deeply about the experience we create for our clients, our community, and each other. We move quickly. We think big. We care about details. We believe energy matters. And we believe the work we do should make a meaningful difference in the lives of the people we touch. We're looking for an Executive Assistant who wants to be an important part of making all of that happen. The Role This is not a traditional administrative position. We are looking for a highly organized, proactive, resourceful Executive Assistant to work closely with our Founder/CEO and help bring structure, clarity, and execution to a very full professional life. You will be part gatekeeper, part air-traffic controller, part problem solver, and part trusted partner. There will be calendars to manage, travel to coordinate, meetings to prepare for, clients to communicate with, projects to move forward, details to remember, and situations that change without much warning. The right person won't simply ask, "What do you need me to do?" They'll learn the business, understand the priorities, anticipate what comes next, and increasingly be able to say, "I've already handled it." That distinction matters to us. What You'll Own Manage and protect the Founder/CEO's calendar, priorities, meetings, appointments, and commitments. Coordinate travel from beginning to end, including flights, hotels, ground transportation, itineraries, reservations, and schedule changes. Prepare the Founder/CEO for meetings, speaking engagements, client conversations, events, and other key commitments. Stay ahead of deadlines, follow-ups, deliverables, and important details so nothing gets lost in the noise. Serve as a professional and thoughtful point of contact for clients, partners, event organizers, vendors, and members of the Cannonball community. Draft, organize, proofread, and manage emails, documents, presentations, notes, itineraries, and other communications. Turn conversations and ideas into action items and make sure those action items actually get completed. Coordinate across the Cannonball team to keep projects moving and communication clear. Help prioritize competing demands when everything feels important. Identify problems early, bring possible solutions, and take ownership of resolving what you can. Create and improve systems that make the Founder/CEO and the broader organization more organized and effective. Support special projects and unexpected needs as they arise. Some travel is required Who Will Thrive Here You're exceptionally organized, but organization alone isn't enough. You have strong judgment. You notice what other people miss. You remember the detail from a conversation three weeks ago that suddenly matters today. You can look at a chaotic calendar and create order. You don't need constant direction to make progress. When something changes, you adjust instead of freezing. When you see a problem, your instinct is to figure it out. You communicate clearly and professionally whether you're speaking with a CEO, a client, a keynote organizer, a teammate, or a vendor. You know when something requires the Founder/CEO's attention and when you can simply take care of it yourself. And you understand that being an exceptional Executive Assistant isn't about completing the most tasks. It's about helping the person and organization you support operate at their best. What We Value Ownership If you say you're handling something, we need to know it's handled. Initiative We value people who think ahead rather than constantly waiting for the next instruction. Details Small things become big things when they're missed. You naturally pay attention. Communication You ask good questions, provide clear updates, and don't allow uncertainty to linger. Energy The way we show up affects everyone around us. We expect professionalism, optimism, composure, and respect. Contribution No job here is "just a job." We want people who care about the impact of their work and the people it affects. Betterment We're not looking for perfection. We are looking for someone who wants to learn, grow, improve systems, receive feedback, and get better. Experience & Skills We're less interested in checking every box than we are in finding the right person, but strong candidates will likely have: Previous experience supporting a founder, CEO, executive, entrepreneur, or senior leader. Exceptional calendar management and scheduling skills. Strong written and verbal communication. Excellent organizational and time-management skills. High proficiency with email, calendars, Microsoft Office and/or Google Workspace, spreadsheets, presentations, and modern productivity tools. Comfort learning new software and technology quickly. Strong problem-solving skills and the ability to make sound decisions independently. Experience coordinating detailed business and personal travel. Ability to manage multiple priorities without losing attention to detail. A track record of reliability, discretion, and sound judgment. The confidence to respectfully push back, ask questions, or flag something when necessary. What Success Looks Like You'll know you're succeeding when: The Founder/CEO is spending more time on the things only he can do. Important commitments aren't being missed. Meetings are prepared for before they happen. Travel feels organized instead of stressful. Follow-ups happen without repeated reminders. The team knows where things stand. Clients and partners feel taken care of. Problems are being solved before they become emergencies. And over time, you understand the Founder/CEO, Cannonball Moments, and our priorities well enough to anticipate what needs to happen next. One Last Thing We take this role seriously because trust is a big deal here. You will have visibility into the business, the calendar, relationships, conversations, opportunities, and challenges that most people never see. We need someone who treats that access with discretion, good judgment, and genuine care. In return, you'll have the opportunity to work closely with an entrepreneurial organization that is growing, creating, experimenting, and trying to make a meaningful impact. If you are looking for a position where you can simply complete a list of assigned tasks each day, this probably isn't the right fit. If you love creating order, solving problems, taking ownership, building trusted relationships, and becoming indispensable to a team doing work that matters, we'd like to meet you.

Pay:

$45,000.00 - $55,000.00 per year

Benefits:

401(k) 401(k) matching Dental insurance Health insurance Paid time off Parental leave

Work Location:

In person