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Remote, Oregon, United States
Remote only
The Opportunity
Project Expedition is looking for a hands-on, AI-forward Head of Client Experience to help us scale an organization already known for exceptional service, without losing the personal touch our clients, travel advisors, partners, and travelers expect.
This is not a strategy-only CX leadership role. We are looking for someone who leads from the front: someone who will learn the product deeply, understand our workflows, spend time in the queue, handle tickets when needed, take ownership of escalations, engage directly with customers, and coach the team from firsthand experience.
Our belief is simple: in travel, service cannot feel automated. Travel is emotional, time-sensitive, and often high-stakes. The right leader will know how to use AI to make our team faster, smarter, more consistent, and more proactive, while preserving the judgment, empathy, and human care that define an exceptional client experience.
You will own the day-to-day performance of the Client Experience team, the systems that support it, and the service philosophy behind it. Your mandate is to turn support into a measurable competitive advantage through operational excellence, product mastery, thoughtful AI adoption, and hands-on leadership.
What You’ll Own
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 be expected to:
Lead, coach, and develop team leads and support specialists across email, chat, and phone.
Spend regular time in the ticket queue and reporting to understand customer pain points, product gaps, process friction, and team execution.
Personally handle escalations, difficult customer situations, VIP/advisor issues, and time-sensitive travel problems when needed.
Learn and master the Project Expedition product, booking flows, supplier/operator workflows, advisor needs, internal tools, and customer journey.
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.
AI + Human Touch
We are not looking for someone who wants to “automate customer service” at the expense of quality. We are looking for someone who understands how to combine AI, automation, better systems, and human judgment to deliver a higher level of service than either people or technology could deliver alone.
You should be excited to explore and implement practical AI use cases such as:
AI-assisted ticket triage, routing, prioritization, and summarization.
Agent-assist tools that help the team respond faster while preserving warmth, accuracy, and brand voice.
Better knowledge management and internal search so the team can answer confidently, accurately, and consistently.
QA support, trend detection, sentiment analysis, and coaching insights.
Automation of repetitive administrative work so humans can focus on complex, emotional, urgent, or high-value interactions.
Proactive alerts and workflows for time-sensitive travel issues, supplier changes, cancellations, itinerary questions, and customer risk signals.
You should also know where not to automate. The right person will understand that travel support often requires nuance: last-minute changes, disappointed customers, special requests, refunds, safety concerns, travel advisor relationships, and high-stakes moments where empathy and judgment matter.
What We’re Looking For
Must-Have Experience
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.
Strongly Preferred
Travel, hospitality, marketplace, tour/operator, OTA, or time-sensitive operations experience.
Experience supporting travel advisors, B2B partners, suppliers, or high-expectation customers.
Experience with international customers, multi-time-zone teams, or 24/7 coverage models.
Experience partnering with Product/Engineering on tooling, automation, AI-assist, self-service, or analytics improvements.
Experience improving both efficiency and service quality without making the customer experience feel robotic.
You’ll Thrive Here If You…
Believe exceptional service can be a true competitive advantage.
Are as comfortable in a dashboard as you are in a customer escalation.
Do not view frontline work as beneath leadership.
Like getting into the weeds, finding the pattern, fixing the system, and coaching the team through the change.
Have strong opinions on how AI should improve customer experience, but equally strong judgment about where human empathy needs to remain central.
Can create clarity in messy, fast-moving, operationally complex environments.
Hold a high bar for tone, ownership, speed, accuracy, and follow-through.
Care deeply about travel and understand that when something goes wrong on a trip, the customer experience becomes personal very quickly.
This Role Is Probably Not a Fit If…
You want a purely strategic leadership role and do not want to handle tickets, escalations, or frontline workflows.
You prefer managing through reports only and do not want to learn the product deeply.
You think AI should replace human service rather than strengthen it.
You are uncomfortable with ambiguity, operational detail, or fast-changing priorities.
You have led teams before but have not built systems, coached quality, owned metrics, or improved day-to-day execution.
You are not energized by customer-facing problem solving.
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 $10,500 with 2 completely covered plans)
401K company plan
Annual work from home budget $500
Annual training budget of $250
TSA Precheck
Annual Project Expedition tour credits of $750
Employee discounts on thousands of tours and activities
Additional Information
This is a remote role open to candidates based in the United States. Currently, we are unable to hire employees residing in New York or California.