Guest Services Supervisor

Who We Are & What We’re Building

At Goodwin, we build tech for companies that sell private charter flights. In this industry, brokers work directly with travelers to source trips and manage client relationships, while operators own and manage the aircraft and crews that actually fly them.

Behind the scenes, brokers have traditionally juggled nonstop phone calls, email threads, and spreadsheets to match each client request with the right aircraft at the right time. It is fast, detail-heavy work where timing and accuracy matter.

Our platform brings structure and speed to that process. Brokers use Goodwin to send requests, compare options, and manage trips in one place instead of juggling dozens of conversations.

Our technology drives efficiency and our operations team drives follow-through. Together, we help brokers move quickly and confidently when details matter most so they can focus on serving their clients and growing their business.

Founded in 2022 and headquartered in Columbus, Ohio with distributed talent across the US, Goodwin is on a fast-growth trajectory as we redefine private aviation technology from the ground up.

Why This Role Exists

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. As Goodwin’s operation scales, 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. Give timely, specific feedback that reinforces strong work and addresses opportunities for improvement. Use everyday situations to strengthen skills and judgment, and follow up to ensure feedback translates into progress.

• Own team performance and accountability
  • Monitor individual performance, lead performance reviews, and address concerns early through clear expectations and consistent follow-through. Partner with the Director of Operations and People team on formal performance improvement and employee concerns when needed.

• Develop team members’ skills and expertise
  • Establish development goals with each direct report and regularly revisit progress. Identify training needs, provide opportunities to take on more complex work, and help team members build deeper expertise and readiness for greater responsibility.

• Support team engagement and connection
  • Recognize contributions, invite feedback, and create an environment where people feel comfortable asking questions and raising concerns. Stay attentive to workload, morale, and barriers to success, and take action to keep the team supported and engaged.

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 and not limited to performance reviews.
• Your direct reports’ skills, expertise, and judgment are improving. They are handling increasingly complex work with greater confidence and independence.
• Regular one-on-ones and development conversations lead to clear actions and visible progress.
• Performance concerns are addressed early. Team members receive clear expectations, support, and consistent follow-through.
• Team members describe you as accessible, fair, and invested in their growth. They feel recognized and comfortable raising questions or concerns.
• You understand what is affecting your team’s engagement and take action to address concerns within your control.
• You consistently make time for coaching, development, and people management alongside your own trip management responsibilities.

What We’re Looking For

Required

• 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 — setting standards, coaching in the moment, and driving accountability
• Track record of managing complex, high-stakes situations with sound judgment and composure when multiple things are going wrong simultaneously
• Strong client and broker relationship management — building trust and credibility consistently over time
• Experience contributing to process design, improvement, or team structure in a scaling operation
• A genuine orientation toward developing people — someone who finds it meaningful to make others better at their work
• 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