[Hiring] Guest Services Supervisor @Goodwin

Role Description

The Guest Services Supervisor is the day-to-day leader of the trip management team and direct people manager for up to six team members. This role exists to ensure that the team is well-run, well-supported, and consistently delivering on the client experience that defines Goodwin’s reputation.

This is a working leadership role. The Supervisor carries a share of the Guest Services Lead workload while running the daily team operation and taking ownership of their direct reports’ performance, development, and engagement. They provide consistent feedback in the flow of work, help team members deepen their expertise, and build the team’s ability to handle increasingly complex work independently.

The Supervisor is the second and final escalation point when a Lead cannot resolve a situation independently, and maintains real-time awareness of where the team is under pressure at any level of the structure—stepping in to plug gaps before they become problems.

What You’ll Work On

• Directly manage up to six team members
• Set clear expectations for performance, quality, communication, and accountability
• Hold regular one-on-ones, understand each person’s strengths and growth opportunities, and serve as their primary source of guidance and support
• Provide in-the-moment leadership, coaching, and feedback
• Be present and accessible during active operations
• Own team performance and accountability
• Develop team members’ skills and expertise
• Support team engagement and connection

How You’ll Know You’re Succeeding

• Team members understand what is expected of them and where they stand
• Feedback is timely, specific, and part of everyday work
• Your direct reports’ skills, expertise, and judgment are improving
• Regular one-on-ones and development conversations lead to clear actions and visible progress
• Performance concerns are addressed early
• Team members describe you as accessible, fair, and invested in their growth
• You understand what is affecting your team’s engagement and take action to address concerns
• You consistently make time for coaching, development, and people management alongside your own trip management responsibilities

Qualifications

• Significant experience in private aviation trip management, charter operations, or a directly comparable service operations environment with exposure to the full trip lifecycle including international trips
• Demonstrated experience leading or informally leading a team in a live operations environment
• Track record of managing complex, high-stakes situations with sound judgment and composure
• Strong client and broker relationship management
• Experience contributing to process design, improvement, or team structure in a scaling operation
• A genuine orientation toward developing people
• Availability to work a flexible schedule across 7 days per week between 5:00am and 4:00am Eastern
• Authorization to work in the United States without current or future sponsorship

Preferred

• Prior experience in a formal supervisory or management role in aviation operations or a comparable service environment
• Familiarity with AI-assisted operations and how to integrate AI agents effectively into a human team workflow
• Experience building or refining SOPs, training programs, or team development frameworks
• Track record of navigating the tension between scaling operations and maintaining a high-quality, relationship-driven client experience