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About the Role

The Customer Success Supervisor provides leadership, coaching, operational oversight, and escalation support to the Global Customer Success team, empowering frontline agents to deliver exceptional service. This role acts as a senior subject matter expert, driving team capability, service excellence, and continuous improvement initiatives.

Responsibilities

Provide Outstanding Support Across Channels
Lead and support Customer Success Specialists and BPO partners in delivering exceptional multi-channel support across phone, chat, email, and task-based interactions.
Act as the senior escalation point for complex, high-risk, or high-impact customer, trade partner, and stakeholder concerns.
Provide expert guidance on TTC products, policies, systems, procedures, and customer recovery strategies.
Support booking retention, customer loyalty, and future sales opportunities while balancing customer, commercial, and operational outcomes.
Maintain operational accuracy, quality standards, brand integrity, and customer experience across all interactions.
Effectively manage competing business priorities while supporting operational performance and service delivery.
Escalation Leadership & Stakeholder Management
Take ownership of complex escalations and sensitive stakeholder matters, driving resolution through to completion.
Exercise sound judgement when assessing customer, commercial, financial, operational, and reputational impacts.
Build and maintain strong relationships with internal departments and external stakeholders to facilitate timely issue resolution.
Support leadership in identifying root causes, emerging risks, and trends to improve processes and reduce repeat escalations.
Demonstrate resilience, empathy, professionalism, and composure when managing challenging customer and stakeholder situations.
Act as the primary escalation support resource during periods where leadership is unavailable.
Ensure escalations are accurately documented, managed, and reported through appropriate systems and processes.
Operational Excellence, Data Review & Continuous Improvement
Review and analyse performance metrics, service trends, escalation volumes, customer insights, and operational data to identify opportunities for improvement.
Develop and maintain reporting that provides actionable insights into customer experience, operational effectiveness, service quality, and workload distribution.
Monitor trends across escalations, customer feedback, and business performance to support informed decision-making.
Lead continuous improvement initiatives focused on service excellence, process optimisation, knowledge management, and operational efficiency.
Participate in calibration sessions, quality reviews, and feedback forums to ensure consistency, alignment, and best practice adoption.
Support implementation of process, system, and workflow enhancements across the Customer Success function.
Team Leadership, Coaching & Capability Development
Provide day-to-day guidance, support, coaching, and mentoring to Customer Success Specialists and BPO partners.
Monitor workload allocation and support resource management to ensure service levels and business priorities are achieved.
Develop team capability through structured coaching, performance feedback, training, and knowledge-sharing initiatives.
Lead onboarding activities for new team members and support ongoing development plans for existing team members.
Own and maintain Customer Success documentation, knowledge resources, standard operating procedures, and process guidelines.
Represent the Customer Success function in cross-functional meetings, providing insights, recommendations, and operational updates.
Foster a positive, collaborative, and customer-focused team culture.
Remain flexible and responsive to changing business needs, undertaking additional responsibilities as required.

Requirements

Minimum 24 months' experience in a Contact Center, Customer Success, Customer Service, Reservations, or operational support environment with a strong track record of performance.
Experience managing complex escalations and stakeholder enquiries.
Proven ability to coach, mentor, and support the development of others.
Experience working with customer relationship management (CRM) platforms, support and customer support technologies and customer experience metrics; Salesforce experience preferred.
Strong knowledge of Tier 2 support operations, escalation workflows, and customer experience metrics, with a proven ability to diagnose root causes across the customer lifecycle.
Strong analytical, problem-solving, and decision-making capability.
Demonstrated ability to balance customer, commercial, and operational outcomes.
Excellent written and verbal communication skills.
Strong stakeholder management and relationship-building capability.
Proven ability to work autonomously and confidently make decisions within delegated authority.
Commitment to delivering exceptional customer experiences while supporting business objectives.

Skills

Communication & Influence
Customer Focus
Adaptability
Quality & Attention to Detail
Developing Self & Others

Location

Remote (Canada)
Hybrid (Toronto, Ontario)

Work Type

Remote
Hybrid
Full-time

Experience Level

Minimum 24 months experience in a Contact Center, Customer Success, Customer Service, Reservations, or operational support environment

About the Company

At TTC, we are Enriching lives by connecting people and places.
For over 100 years, we’ve been bringing the world closer together by crafting journeys that create lasting memories, lifelong friendships and meaningful cultural connections.
Across more than 70 countries and our award-winning brands, we design and deliver travel experiences that go beyond sightseeing - they change perspectives.
Behind every unforgettable journey is a passionate team making it happen. That’s where you come in.
OUR VALUES
Everything we do is guided by our five shared commitments: Value Every Voice - We put people first. Act with Integrity - We do what’s right. Explore Beyond Boundaries - We’re driven by curiosity. Own the Outcome - We take responsibility for our decisions. Succeed Together - We’ve got each other’s backs.