Project Expedition

Compensation

Full Description

The Opportunity Project Expedition is looking for a tech-forward Head of Client Experience to help us scale an organization that’s already known for exceptional service —without losing the personal touch our clients expect. This role is for a leader who blends world-class support operations with expertise in using technology and AI to drive speed, consistency, and quality. We don’t believe in “automating customer service.” We believe in augmenting our team with better tools, clearer systems, and smarter workflows so they can deliver standout experiences more efficiently and more consistently. You’ll own the day-to-day performance of Client Experience and the systems, coaching, and strategy behind it—turning support into a measurable competitive advantage through operational excellence, thoughtful leadership, and modern tooling. Responsibilities: Manage team leads and support specialists across channels (email, chat, and phone). Leverage AI and technology to develop scalable efficiencies. Coach, develop, and retain top talent; create clear career paths and standards of excellence. High-quality, personal service is a USP – it should not be automated, it should be augmented. Leverage AI and technology to empower the team to achieve better metrics and deliver better service. Own key metrics: CSAT/NPS, SLA/response time, resolution time, reopen rate, QA scores, contact rate, escalation rate, refunds/chargebacks (where applicable). Establish QA program and calibration routines that are fair, consistent, and measurable. Improve workforce planning: schedules, coverage models, training ramps, and peak-season readiness. Leverage data analysis to identify opportunities for growth, efficiency, and improvement. Improve retention and customer loyalty by ensuring every interaction builds trust. Partner with Product/Engineering on support tooling—including AI assist, automation, and analytics—without sacrificing quality. Bring clarity and recommendations to leadership: what’s working, what’s broken, what needs investment. Taking ownership – even when it means personally responding to clients and handling escalations. What we’re looking for: Must-have experience 6–10+ years in Customer Support / Client Experience / Customer Success, including 3+ years managing managers or leading a department. Proven track record scaling support in a high-volume environment (marketplace, travel, e-commerce, logistics, fintech, or similar). Experience leveraging AI and technology to drive an organization forward. Strong analytical mindset: you’re comfortable with dashboards, metrics, cohorts, and using data to drive decisions. Excellent written communication and judgment. You can coach tone, clarity, and empathy—and handle escalations yourself when needed. Experience building systems: SOPs, playbooks, QA frameworks, onboarding and training programs. Strongly preferred Travel, hospitality, marketplace, or time-sensitive operations experience. Experience partnering closely with Product/Engineering on tooling improvements. Experience with automation, self-service, and/or AI-assist for support. Familiarity with international customer bases and multi-time-zone, 24/7 teams. You’ll thrive here if you… Love making “exceptional service” a differentiator. Are equal parts operator (process, metrics, execution) and leader (coaching, culture, standards). Get satisfaction from reducing chaos through systems—and still stay human and empathetic. Know how to balance policy with judgment and do the right thing for the customer without creating precedent risk. Why join us Support is central to our strategy and growth—not an afterthought. You’ll have real influence on systems, staffing, tooling, and customer outcomes. You’ll lead a team that touches every part of the business and directly helps to drive sales. Benefits Annual company bonus (up to a total of $3,000, based on company targets - 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 Annual Project Expedition tour credits of $750 Employee discounts on thousands of tours and activities Additional Information While we are excited to grow our team, we’re currently unable to hire employees residing in New York or California.