Director of Member Experience & Operations
YPO Naples Chapter
Naples, Florida | Flexible (In-Person Aug-May + Remote June-July)
*** This application requires an email follow up to be considered for this position.
This is not a typical job.
This is an opportunity to sit at the center of a community of high-performing CEOs and business leaders—and help shape the experiences that fuel their growth, connection, and impact.
YPO (Young Presidents’ Organization) is a global leadership community of more than 29,000 chief executives. The Naples Chapter is being built with intention—to deliver exceptional, high-touch experiences that members genuinely look forward to.
We are not trying to be average.
We are building something special.
This role is for someone who takes pride in creating seamless, thoughtful, and elevated experiences—and who thrives in an environment where expectations are high and the people are exceptional.
A Note from the Chapter Chair
We are building a chapter that people are proud to be part of—not just because of who is in the room, but because of how it feels to be part of it.
I am looking for someone who is:
- Highly accountable
- Proactive and anticipatory
- Energized by working with high-caliber people
- Calm under pressure and detail-oriented
- Someone who finishes things and follows through
This is a role where you will have ownership. You will not be micromanaged—but you will be expected to deliver.
We operate as a team, and communication matters. You will report directly to me, and we will connect weekly to ensure alignment, momentum, and support.
If you take pride in doing things exceptionally well and enjoy creating meaningful experiences for others, this could be a great fit.
What This Role Really Is
This is not just event planning.
This is not just administration.
This is experience ownership.
You are the person ensuring that every interaction a member and their family has with YPO Naples feels:
• Welcoming and inclusive
• Thoughtfully curated
• Seamless and effortless
• Rooted in connection and belonging
• Meaningful and memorable
You are the operational heartbeat of the chapter.
What Success Looks Like (First 6 Months)
- Events run seamlessly—from communication to execution—with strong member attendance and engagement
- Members feel informed, cared for, and excited about what is coming next
- The board experiences you as organized, proactive, and easy to work with
- Communication is consistent, polished, and on-brand across all channels
- You anticipate needs before they are asked
- You establish a weekly reporting rhythm with the Chapter Chair (priorities, progress, risks, next steps)
- You build simple systems that make the chapter easier to run over time
Core Responsibilities
Member Experience & Events
- Plan and execute all chapter events in partnership with the Learning Officer—from small dinners to signature experiences
- Own all event logistics: venues, vendors, catering, AV, run-of-show, and on-site execution
- Create and manage all event communications, registrations, and follow-up
- Ensure every event feels polished, thoughtful, and well-run
Communication
- Serve as the voice of the chapter across email, WhatsApp, and other platforms
- Draft clear, warm, and professional communications
- Maintain consistency and quality across all member touchpoints
Board & Chapter Operations
- Support the executive committee with agendas, meeting preparation, and follow-up
- Maintain organization across chapter activities, timelines, and priorities
- Ensure strong coordination across officers
Membership & Data
- Support membership tracking, onboarding, and engagement
- Maintain accurate data and systems
- Assist with renewals and reporting
Financial & Administrative Oversight
- Track budgets, expenses, and invoices
- Ensure vendors are paid and records are organized
- Maintain operational documentation and systems
How You Will Operate
Ownership
You own outcomes. You take initiative and follow through without needing to be asked.
Communication & Accountability
- Weekly check-in with the Chapter Chair
- Clear reporting on priorities, progress, and challenges
- No surprises
Flexibility with Responsibility
- This role averages ~30 hours per week, with flexibility depending on events and seasonality
- Some weeks will require more time (events), others less
- Evenings and occasional weekends are part of the role
Who Thrives in This Role
You might be a great fit if you:
- Have a background in event planning, hospitality, executive support, or member-based organizations
- Naturally think ahead and anticipate needs
- Take pride in details that others overlook
- Enjoy working with high-performing, driven individuals
- Are highly organized but also adaptable
- Like having autonomy but also being held accountable
- Are energized by creating meaningful experiences
Ideal Background (Not Required, But Helpful)
- 5–8+ years in event planning, hospitality, executive assistant, or similar roles
- Experience supporting senior leaders or high-end clientele
- Comfortable managing multiple priorities and stakeholders
- Strong written communication skills
- Proficiency with Google Suite, Excel, and communication tools
Travel & YPO Integration
- As part of this role, you will attend two out-of-state, multi-day YPO trainings and team-building workshops annually
- These gatherings connect you with Chapter Managers and leaders across the YPO network and are designed to elevate the quality and consistency of the member experience
- Travel expenses will be covered
Compensation & Start Date
- Salary: $65,000+ (1099 independent contractor)
- This is designed as a flexible, outcome-based role (~30 hours/week on average, likely less hours in June-July and more hours Aug-May)
- Ideal for someone seeking both stability and flexibility (including those with a complementary business or consulting work)
- Target start date: June 1, 2026. Will need to attend and support the chapter’s closing event on the evening of June 4, providing an opportunity to onboard, observe, and begin transitioning into the role
Location & Seasonality
- This role requires being based in Naples, Florida from mid-August through early June, aligned with the chapter’s primary event season
- In-person presence is required for events, including some evenings and occasional weekends
- During the summer months (June–August), the role shifts to a lighter, primarily remote schedule focused on:
- Membership renewals (July cycle)
- Planning and preparation for the upcoming season
This role follows the natural rhythm of the Naples season—highly engaged and in-person during the core months, with a lighter, flexible, and remote summer period. It is well-suited for someone who values both meaningful work and seasonal flexibility.
Final Thought
This role is for someone who cares about the experience others have.
If you are someone who notices the details, takes pride in execution, and enjoys being around people who are building and leading at a high level—this is a unique opportunity to be part of something meaningful.
How to Apply
Please submit via email with the subject line "YPO Naples Experience - {your name}” to janetjohanson@live.com:
· A short note (or 2–3 minute video) on why this role interests you
· Your resume
· Include the phrase “YPO Naples Experience” in the subject line of your email so we know you read this description fully
· (Optional but encouraged) An example of an event or experience you planned, including any invitation or communication you created
