Head of Client Experience

The Opportunity

The Opportunity Project Expedition is seeking a hands-on, AI-forward Head of Client Experience to lead our growing support team. This role is not just about strategy; it's about leading from the front, understanding our workflows, and delivering exceptional service.

About the role

You will lead our Client Experience function across email, chat, and phone, managing team leads and support specialists while staying close enough to the work to understand what is really happening on the front lines. You will personally handle escalations, difficult customer situations, VIP/advisor issues, and time-sensitive travel problems when needed.

Responsibilities

• Lead the Client Experience team, manage team leads and support specialists, and stay close to the work to understand what is really happening on the front lines.
• Spend regular time in the ticket queue and reporting to understand customer pain points, product gaps, process friction, and team execution.
• Personalize customer interactions, coach the team, and build a culture where leaders model the standard, not just measure it.
• Own key operating metrics, including CSAT, SLEs, QA scores and other service-quality indicators.
• Establish and improve QA programs, calibration routines, coaching cadences, SOPs, escalation paths, and training materials.
• Improve workforce planning, scheduling, coverage models, training ramps, and peak-season readiness.
• Use data to identify the root causes of customer friction and turn those insights into clear operational, product, or tooling improvements.
• Partner closely with Product, Engineering, Sales, and Supplier teams to improve support tooling, internal workflows, and the customer experience.
• Bring clear recommendations to leadership on what is working, what is broken, what needs investment, and where we can scale more effectively.

Requirements

• 6–10+ years in Customer Support, Client Experience, Customer Success, Travel Operations, or a similar customer-facing function.
• 3+ years managing managers, team leads, or a meaningful support/client experience organization.
• Proven experience scaling support or service operations in a high-volume, time-sensitive environment such as travel, hospitality, marketplace, e-commerce, logistics, fintech, or similar.
• A true lead-from-the-front mentality. You are comfortable jumping into tickets, calls, escalations, workflows, and customer issues to understand the work and set the standard.
• Strong product curiosity. You are the type of leader who wants to learn the product deeply enough to diagnose issues, coach effectively, improve workflows, and represent the customer’s voice internally.
• Practical AI and technology fluency. You have used, implemented, or meaningfully experimented with AI, automation, support tooling, knowledge-based systems, or agent-assist workflows to improve service quality and efficiency.
• Strong analytical ability. You are comfortable with dashboards, metrics, cohorts, QA data, and operational reporting, and you know how to turn data into action.
• Excellent written communication, tone, judgment, and customer empathy.
• Experience building systems: SOPs, playbooks, macros, QA frameworks, escalation paths, onboarding programs, training programs, and performance standards.
• Ability to balance policy, precedent, customer trust, and business judgment.

Qualifications

• Must-have experience includes 6–10+ years in Customer Support, Client Experience, Customer Success, Travel Operations, or a similar customer-facing function.
• 3+ years managing managers, team leads, or a meaningful support/client experience organization.
• Proven experience scaling support or service operations in a high-volume, time-sensitive environment such as travel, hospitality, marketplace, e-commerce, logistics, fintech, or similar.
• A true lead-from-the-front mentality. You are comfortable jumping into tickets, calls, escalations, workflows, and customer issues to understand the work and set the standard.
• Strong product curiosity. You are the type of leader who wants to learn the product deeply enough to diagnose issues, coach effectively, improve workflows, and represent the customer’s voice internally.
• Practical AI and technology fluency. You have used, implemented, or meaningfully experimented with AI, automation, support tooling, knowledge-based systems, or agent-assist workflows to improve service quality and efficiency.
• Strong analytical ability. You are comfortable with dashboards, metrics, cohorts, QA data, and operational reporting, and you know how to turn data into action.
• Excellent written communication, tone, judgment, and customer empathy.
• Experience building systems: SOPs, playbooks, macros, QA frameworks, escalation paths, onboarding programs, training programs, and performance standards.
• Ability to balance policy, precedent, customer trust, and business judgment.

Skills

• Hands-on experience with AI and automation to improve service quality and efficiency.
• Strong product curiosity and ability to learn deeply about the product and workflows.
• Effective communication and customer empathy.
• Experience building and implementing systems to improve service quality and efficiency.
• Ability to balance policy, precedent, customer trust, and business judgment.

Benefits

• Annual company bonus, up to $3,000 based on company targets and deferred eligibility.
• 15 days of leave (increases to 20 days at 2 years tenure).
• Company Healthcare Plan (Company contribution $9K with 2 completely covered plans).
• 401K company plan.
• Annual work from home budget $500.
• Annual training budget of $250.
• TSA Precheck.
• Project Expedition tour credits of $750.
• Employee discounts on thousands of tours and activities.

Pay

Competitive salary and benefits package.

Schedule

Remote role open to candidates based in the United States. Currently, we are unable to hire employees residing in New York or California.