Executive Assistant to the Founder & CEO

Executive Assistant to the Founder & CEO

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

Role Summary

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 PopStroke 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 PopStroke, 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, texts, and conversations and ensure appropriate follow-through.
• Maintain a running understanding of the CEO’s highest priorities and proactively surface anything requiring his attention.
• Know when to remind, when to push, when to protect his time, and when to simply handle something without involving him.

Business Integration

• Become deeply knowledgeable about PopStroke, its venues, leadership team, growth strategy, operating priorities, partners, investors, and key relationships.
• Develop a strong understanding of the CEO’s other businesses, investments, ventures, and professional interests.
• Stay connected to major priorities across the organization so the CEO has the context he needs without having to chase information.
• Build strong working relationships with PopStroke’s executive leadership team and other key internal and external partners.
• Serve as a trusted connector between the CEO and leaders throughout the organization while maintaining appropriate confidentiality.
• Coordinate across executives, business partners, investors, advisors, vendors, and other key stakeholders.
• Attend meetings when appropriate to capture decisions, commitments, and next steps.
• Ensure important conversations translate into action and follow-up occurs without the CEO having to personally manage it.

Meeting & Communication Management

• Ensure the CEO enters important meetings prepared with the appropriate background, documents, context, and key decisions required.
• Coordinate agendas, materials, presentations, talking points, and other preparation as needed.
• Maintain awareness of incoming requests and help prioritize communication based on urgency and importance.
• Draft, coordinate, or facilitate correspondence and follow-up on the CEO’s behalf when appropriate.
• Track outstanding requests, decisions, introductions, and commitments.
• Build and maintain strong relationships with the people the CEO interacts with most frequently and ensure communication reflects the professionalism, responsiveness, and hospitality expected of the Founder & CEO.

Travel & Logistics

• Own complex domestic and international travel planning, including flights, accommodations, ground transportation, reservations, itineraries, and last-minute changes.
• Build travel schedules around the CEO’s priorities rather than simply booking logistics.
• Anticipate what the CEO will need before, during, and after travel.
• Coordinate business meetings, venue visits, dinners, events, and personal commitments surrounding travel.
• Remain highly responsive when plans inevitably change and quickly create alternatives.
• Ensure the CEO always knows where he needs to be, when he needs to be there, who he is meeting, and what he needs to know.

Personal & Lifestyle Support

Because the CEO’s professional and personal worlds frequently intersect, this role will provide trusted support beyond traditional business responsibilities when needed.

• Help coordinate personal appointments, reservations, travel, events, family logistics, and other commitments that affect the CEO’s schedule and availability.
• Partner with appropriate personal, household, family, or external resources to ensure seamless coordination.
• Handle sensitive personal matters with exceptional judgment and confidentiality.
• Approach personal requests with the same level of ownership, urgency, and attention to detail as business priorities.
• Create simplicity around the CEO so he can remain focused on the things that matter most.

How You’ll Work

This role requires someone who thrives in a founder-led environment where the pace is fast, priorities can change quickly, and not every responsibility comes with a playbook.

You will need to:

• Be proactive. If the CEO has to consistently tell you what comes next, you are already behind.
• Own it. Once something is handed to you, you own it through completion.
• Connect the dots. Understand how people, meetings, conversations, priorities, and commitments relate to one another.
• Protect the CEO’s time and focus. Be thoughtful about where his time, energy, and attention are spent while safeguarding important relationships and commitments.
• Move quickly. Urgency matters, but never at the expense of judgment or quality.
• Stay flexible. Plans will change. Priorities will shift. The right person adapts without becoming frustrated or overwhelmed.
• Use judgment. Know what you can solve independently and what truly requires the CEO’s involvement.
• Be extraordinarily discreet. You will have access to highly confidential business, financial, personnel, and personal information.
• Build trust. Your relationships with the CEO, his family, executives, partners, and other stakeholders will be critical to your success.
• Make it happen. “That’s not my job” cannot exist in this role.

What You Bring

• Significant experience supporting a CEO, Founder, Chairman, entrepreneur, or similarly senior executive in a complex, high-demand environment.
• Prior experience serving as an Executive Assistant to a CEO is required.
• Strong preference for experience supporting a founder-led or owner-led organization where business and personal priorities often intersect.
• Demonstrated experience managing an exceptionally complex executive calendar with constantly competing priorities.
• Experience supporting multiple businesses, investments, ventures, or entities is highly preferred.
• Exceptional organizational skills and the ability to manage significant amounts of information without losing details.
• Strong business acumen and genuine interest in understanding how the businesses the CEO leads and invests in operate.
• Exceptional written and verbal communication skills.
• Ability to interact comfortably and professionally with senior executives, investors, business partners, high-profile individuals, team members, and personal contacts.
• Excellent judgment and the ability to make decisions independently.
• High emotional intelligence and the ability to read people, situations, and priorities.
• Exceptional discretion and a proven track record handling confidential and sensitive information.
• Strong technology skills and the ability to quickly learn and leverage tools that improve organization, communication, and efficiency.
• A service mindset without being passive—the best person for this role is confident enough to respectfully challenge, redirect, remind, and push when needed.
• Ability and willingness to occasionally travel and support early mornings, evenings, weekends, or changing schedules when the CEO’s commitments require it.

What We’re Looking For

You are someone who gets tremendous satisfaction from making a highly driven executive more effective.

You notice things other people miss. You remember the conversation from three weeks ago that suddenly matters today. You see the calendar conflict before anyone else does. You know which meeting can move, which relationship needs extra attention, which follow-up hasn’t happened, and what the CEO is likely going to ask for next.

You don’t wait for a task list.

You create order in a fast-moving environment without slowing it down. You are calm when plans change, resourceful when there is no obvious answer, and persistent enough to get things done.

You are comfortable being behind the scenes while having tremendous influence on how effectively the Founder & CEO operates.

Most importantly, you understand that trust is everything in this role.

Location & Commitment

This role is based in Jupiter, Florida and requires a strong in-person presence. The nature of the position requires close proximity to the CEO and the ability to support a schedule that does not always fit neatly within traditional business hours.

This individual must be fully committed to supporting the CEO and the businesses, relationships, and priorities surrounding him. Flexibility, responsiveness, and availability are inherent to the position.

This is an opportunity for someone who wants to be deeply embedded alongside a Founder & CEO—not simply adjacent to the business—and who is energized by the responsibility, pace, access, and trust that comes with it.

PopStroke is an Equal Opportunity Employer

PopStroke participates in E-Verify and will provide the federal government with your Form I-9 information to confirm that you are authorized to work in the U.S.