Executive & Personal Assistant to CEO

Serv, a global executive recruitment partner, is hiring on behalf of our client, Waystone Advisors, for an exceptional Executive & Personal Assistant to the CEO.

Join the Team:

Most financial firms are built around one finish line: retirement at 65. Save enough, wait long enough, and eventually you may have the freedom to stop working.

Waystone Advisors believes there’s a better way.

Founded in 2012, Waystone is built around the belief that financial independence isn’t a retirement date—it’s about creating the freedom to make work optional. They help high earners, including physicians, pilots, tech professionals, entrepreneurs, and real estate investors, build wealth and passive income with the goal of achieving that freedom years, or even decades, earlier.

As an independent, SEC-registered firm, Waystone answers to its clients rather than a traditional product shelf. This allows the team to bring together traditional investments with alternative strategies, including real estate, giving clients access to opportunities historically more common among the ultra-wealthy.

Their mission is simple: make your money work harder than you do.

Waystone believes financial independence may be closer than many people realize. Every advisor on the team plays a direct role in helping clients see what’s possible and build a strategy to get there.

To learn more, explore these resources: Bonnie Koo, Austin Dean: Why 401(k)s Are ‘Money Jail’, 3 Nontraditional Strategies the Wealthy Use

The Role

As the Executive & Personal Assistant to the CEO, you will act as a trusted right hand, providing high-level administrative, operational, and personal support.

You will be responsible for managing the CEO's calendar, communications, scheduling, and competing priorities while ensuring important projects and commitments move forward.

This is more than a traditional administrative position. We are looking for someone who can anticipate needs, solve problems independently, and take ownership of the details that allow the CEO to focus on growing the business, serving clients, leading the team, as well as be present with his family and be an example of what healthy financial independence can look like.

Key Responsibilities

Executive & Administrative Support

• Proactively manage the CEO's calendar, appointments, meetings, and daily priorities.
• Coordinate internal and external meetings, ensuring schedules are organized and time is used effectively.
• Prepare meeting agendas, briefing materials, presentations, and follow-up communications.
• Manage inbox organization, correspondence, and communication on behalf of the CEO as appropriate.
• Track action items, deadlines, and commitments to ensure timely follow-through.
• Anticipate scheduling conflicts, logistical challenges, and upcoming needs before they become issues.

Business & Operational Coordination

• Support the CEO in managing key business initiatives, special projects, and operational priorities.
• Coordinate with internal team members, clients, and external partners to ensure seamless communication.
• Assist with client scheduling, meeting preparation, documentation, and follow-up.
• Maintain organized systems for tracking projects, priorities, and important information.
• Identify opportunities to improve workflows, processes, and overall executive productivity.
• Leverage technology, automation, and AI tools to streamline administrative responsibilities.

Personal & Lifestyle Support

• Manage personal appointments, reservations, travel arrangements, and scheduling.
• Coordinate personal commitments alongside business priorities to create a well-organized schedule.
• Assist with household-related coordination, service providers, and personal logistics as needed.
• Research, organize, and execute personal projects and requests.
• Handle sensitive personal matters with professionalism, discretion, and confidentiality.
• Serve as a reliable point of contact to help simplify the CEO's day-to-day responsibilities.

Who You Are

Core Traits

• Proactive Operator: You anticipate needs, identify potential challenges, and take action before being asked.
• Relentless Finisher: You follow through on commitments and ensure no details fall through the cracks.
• Highly Organized: You naturally bring structure, clarity, and efficiency to busy environments.
• Calm Under Pressure: You remain composed and solution-oriented when priorities shift.
• High Ownership: You take responsibility for outcomes and are comfortable making decisions independently.
• Service-Oriented: You genuinely enjoy supporting others and take pride in making their lives easier.
• High Emotional Intelligence: You navigate relationships with professionalism, warmth, and discretion.
• Resourceful Problem Solver: You can figure things out, navigate unexpected challenges, and find solutions without needing constant direction.

Mindset & Motivation

• You enjoy working closely with an entrepreneurial founder and contributing to the success of a growing organization.
• You find satisfaction in creating order, removing obstacles, and helping others operate at their best.
• You are naturally curious, adaptable, and comfortable learning new systems.
• You thrive in a fast-paced environment where no two days look exactly alike.
• You understand the importance of confidentiality, trust, and sound judgment.
• You are comfortable supporting both professional and personal priorities with equal attention to detail.

Work Style

• Exceptionally detail-oriented with high standards for quality and accuracy.
• Able to manage multiple competing priorities without losing sight of deadlines.
• Strong written and verbal communication skills.
• Comfortable operating independently with minimal oversight.
• Flexible, responsive, and able to adapt as business and personal needs evolve.
• Professional and polished when interacting with clients, executives, and external partners.

Experience & Skills

• 3–5+ years of experience as an Executive Assistant, Executive Operations Coordinator, or similar role.
• Experience directly supporting a CEO, founder, entrepreneur, or senior executive strongly preferred.
• Previous experience supporting both business and personal responsibilities is a strong asset.
• Experience in financial services, wealth management, professional services, or another high-touch client environment is an asset.
• Strong proficiency with Google Workspace, Microsoft Office, calendar management, and productivity tools.
• Comfortable adopting AI tools, automation, and new technologies to improve efficiency.
• Excellent organizational, project coordination, and time-management skills.
• Demonstrated ability to handle confidential information and sensitive communications with discretion.
• Strong interpersonal skills and the ability to communicate professionally with high-net-worth clients and senior stakeholders.

Hiring Process

We take our hiring process seriously and evaluate candidates based on both capability and culture fit. Our goal is to ensure you step into a role where you feel genuinely excited and fulfilled. That’s important for you, and it’s equally important for us. Below is a snapshot of what you can expect throughout our hiring process.

Please note that steps may vary slightly depending on the position.

Step One: Video Interview with Serv Recruitment

Step Two: Video Interview with Waystone Leadership

Step Three: Video Interview with additional team members

Step Four: Final Interview & Hiring Decision

Benefits

• Comprehensive health and dental benefits
• Generous paid time off and company holidays
• Employer-supported retirement savings
• Fully remote work environment
• Professional development and ongoing learning opportunities
• Support for additional training and industry designations
• Opportunities for industry exposure, including events and speaking engagements
• Periodic in-person team gatherings

Location: Fully Remote, United States

Salary: 80,000–90,000 base salary + up to 20% performance-based bonus

Serv uses AI tools in our recruitment process, including developing job postings and note-taking during interviews. AI is not used to screen, assess, or select candidates. All resumes are reviewed by a human, and all hiring decisions are made by humans. Any AI-generated output used during the recruitment process is reviewed by a human before action is taken.