Executive Assistant to Founder & CEO

Executive Assistant To The Founder & Ceo

Jupiter, Florida | Executive Support | Founder-Led, High-Growth Environment

The Executive Assistant to the Founder & CEO is a highly trusted, deeply integrated partner responsible for helping the CEO operate at his highest level across Pop Stroke and his broader business and personal ventures.

This is not a traditional Executive Assistant role focused simply on calendar management, travel, and administrative support. This person will become an extension of the CEO—understanding how he works, what matters most, where his time creates the greatest value, and what needs to happen around him to keep priorities moving.

The right person will operate several steps ahead at all times. They will anticipate needs before they are communicated, identify conflicts before they become problems, connect dots across conversations and commitments, and create structure around an incredibly fast-moving Founder & CEO.

This individual will have visibility into nearly every aspect of the CEO's professional world and, when needed, his personal commitments. They must be comfortable operating with an exceptional level of trust, discretion, urgency, flexibility, and ownership.

Success in this role means the CEO spends less time managing the logistics around his life and more time focused on the relationships, decisions, ideas, and opportunities where he can have the greatest impact.

What Success Looks Like

• The CEO's time is intentionally managed around his highest priorities.
• Calendar conflicts, travel challenges, missed follow-ups, and competing commitments are anticipated and resolved before they become issues.
• The CEO rarely needs to ask twice—and, ideally, needs are anticipated before he has to ask.
• Meetings are purposeful, well-prepared, and supported with the right context and information.
• Commitments and follow-ups do not get lost, regardless of how quickly priorities are moving.
• Business and personal schedules work together seamlessly.
• The CEO has a trusted partner who deeply understands his businesses, relationships, priorities, preferences, and operating style.
• Important people around the CEO receive a high level of responsiveness and follow-through.
• The EA knows when to protect the CEO's time, when to create access, when to push something forward, and when something requires his immediate attention.
• The CEO has complete confidence that when something is handed off, it will be owned through completion and executed at an exceptionally high level.

What You'll Own

Executive Partnership & Time Management

• Own and actively manage the CEO's complex and constantly evolving calendar across Pop Stroke, additional business ventures, investments, personal commitments, travel, and key relationships.
• Serve as the primary gatekeeper and steward of the CEO's time, ensuring his schedule reflects his most important business and personal priorities.
• Constantly evaluate competing priorities and make thoughtful decisions about what should move, what should wait, and what requires the CEO's attention.
• Anticipate scheduling conflicts and proactively develop solutions rather than simply identifying problems.
• Understand the purpose and priority behind meetings so the CEO's calendar is not simply "full," but intentionally designed.
• Build appropriate preparation, travel, transition, and thinking time into an otherwise fast-moving schedule.
• Recognize when the CEO is being pulled too far into the details and help redirect time toward the areas where only he can add value.
• Maintain awareness of important dates, deadlines, events, commitments, and personal obligations.

Anticipation & Proactive Support

• Operate several steps ahead of the CEO, anticipating what he will need based on upcoming meetings, travel, conversations, projects, and priorities.
• Learn the CEO's preferences, communication style, decision-making patterns, relationships, and operating rhythm.
• Identify issues early and solve them independently whenever possible.
• Bring solutions—not simply questions or problems.
• Recognize patterns and recurring needs and build systems that make the CEO and organization more effective.
• Track commitments made in meetings, calls,…