Senior Customer Support Supervisor

Join Trulieve - Where Passion Meets Purpose

If you're interested in being part of one of the nation's fastest-growing industries, Trulieve may be the perfect place for you. We are proud to be recognized on TIME's America's Best Companies 2026 List
, an honor awarded to top-performing U.S. organizations based on employee satisfaction, financial strength, and sustainability transparency. Trulieve was one of only two cannabis companies to receive this distinction. If you have passion for helping others and want to make a meaningful impact through your work, this may be the role for you. At Trulieve, we strive to bring our patients the relief they need in products they can trust.

Our plants are hand-grown in carefully controlled environments designed to minimize unwanted chemicals and pests, keeping the cultivation process as natural as possible every step of the way.

To learn more about Trulieve and our mission, please visit

Requisition : 20518

Remote Work Available: No

Job Title: Senior Customer Support Supervisor

Department: Retail Solutions / Customer Support Center

Reports To: Retail Solutions Manager

FLSA Status: Exempt

Location: Clearwater, FL Corporate Office

The Senior Customer Support Supervisor oversees the day-to-day operations of the Customer Support Center, ensuring consistent execution of service standards, performance expectations, and operational efficiency. This role is responsible for leading Supervisors and supporting Senior Customer Support Representatives to deliver high-quality customer experience while maintaining performance across service, quality, and compliance metrics. This role is both a people leader and an active contributor, providing direct support during high-volume periods by handling customer interactions and assist queue requests.

• Lead and oversee daily CSC operations, ensuring service levels, response times, and quality standards are consistently met.
• Directly manage and develop Customer Support Supervisors, ensuring effective coaching, accountability, and performance management.
• Monitor and manage operational metrics, including service levels, escalation trends, and workforce productivity.
• Partner cross-functionally with Retail Operations, IT, and other stakeholders to resolve systemic issues and improve processes.
• Ensure escalations are appropriately managed, documented, and trended to identify root cause and drive improvements.
• Conduct regular team meetings and leadership touchpoints to reinforce priorities, communication, and operational alignment.
• Support staffing and workforce alignment to maintain appropriate coverage against demand.
• Actively support inbound channels (calls, chats, webforms, assist queue) during peak volume or business-critical periods.
• Provide real-time guidance and decision-making support for escalated or complex interactions.
• Drive a culture of accountability, customer focus, and continuous improvement.
• Coach Supervisors on performance management, employee development, and operational execution.
• Identify training needs and partner with leadership to address skill gaps across the organization.
• Participate in special projects and initiatives as assigned.

• Demonstrates a strong commitment to delivering exceptional customer experiences, ensuring issues are resolved effectively and service standards are consistently exceeded.
• Drives performance through accountability and a strong focus on achieving and exceeding team and operational goals.
• Ability to quickly assess complex situations, apply sound judgment, and leverage available resources to drive timely and effective resolutions.
• Communicates clearly and effectively across all levels of the organization, ensuring alignment, understanding, and strong cross-functional partnerships.
• Proven ability to develop leaders and team members through structured coaching, feedback, and performance management, fostering continuous growth and engagement.
• Experience leading distributed teams, with the ability to monitor performance, reinforce accountability, and maintain team engagement in a remote or hybrid environment.
• Demonstrated ability to lead and execute initiatives, including defining scope, managing timelines, and delivering results aligned to business priorities.
• Adapts leadership approach based on team needs and business conditions, effectively balancing direction, support, and autonomy to optimize performance.

• While performing the duties of this job, the employee is:
• Occasionally required to move/traverse throughout entire facility, including tight spaces.
• Accurately communicate and exchange sensitive information and ideas with others, including members of the public; observe/inspect details at varying ranges; operate computing devices
• Occasionally required to manipulate objects of varying sizes and weights (e.g., products, packaging, tools, office machinery): push/pull objects up to 50lbs; lift/carry/position objects up to 50 lbs.; ascend/descend…