Role Description We are currently adding to our growing remote support team and are looking for motivated, organized individuals to join us as Client Planning Specialists. In this role, you'll assist clients throughout the travel coordination process by helping organize trip details, reviewing reservation information, and providing support to help ensure a smooth planning experience. This opportunity is a strong fit for individuals who enjoy working with people, staying detail-focused, and managing multiple tasks in a remote environment. Training, onboarding, and continued guidance are available for all team members, regardless of previous travel industry experience. Key Responsibilities - Support clients with travel planning requests, scheduling needs, and vacation preferences - Assist with coordinating hotels, cruises, transportation, tours, excursions, and other travel services - Research travel availability and compare options through approved supplier and booking systems - Help organize itineraries, confirmations, and reservation details - Provide professional assistance through phone, email, and online messaging platforms - Handle follow-up communication, itinerary revisions, and booking-related updates - Maintain organized client profiles and accurate planning documentation within internal systems - Stay informed on supplier promotions, destination updates, and industry information - Participate in virtual onboarding programs, team meetings, and ongoing training sessions Qualifications - Strong interpersonal and communication abilities - Excellent organizational skills with attention to detail - Ability to manage responsibilities independently in a work-from-home setting - Comfortable using web-based platforms, email, and basic computer systems - Reliable internet connection and professional communication habits - Self-motivated with a positive mindset and willingness to learn - Interest in customer support, hospitality, travel planning, or coordination roles - Must be at least 18 years of age - Applicants must reside in the United States, United Kingdom, Mexico, Australia, Spain, or approved hiring regions Benefits - Fully remote work environment - Flexible scheduling opportunities - Guided onboarding and structured training resources - Ongoing mentorship and professional development support - Access to travel supplier platforms, planning systems, and industry tools - Eligibility for travel-related discounts, incentives, and recognition programs - Career advancement opportunities within an expanding remote team

• Develop a business plan for the member and provider experience that anticipates future growth and technological shifts. • Implement tools and processes to handle thousands of multi-channel tickets (chat, voice, email) per week. • Lead the strategy for integrating AI-driven support tools to automate routine workflows, improve self-service, and enhance "high-touch" human interactions. • Manage escalation processes and collaborate cross-functionally to address the root causes of member and provider issues. • Grow a team of incredible Customer Support Managers, Member Advocates, and a Workforce Management (WFM) Analyst. • Ensure the team meets OKRs, SLAs, and KPIs, including CSAT, chat first response time, and call answer rates. • Unlock support interaction data to provide actionable insights for Product, Sales, and Operations teams. • Lead efforts in quality management, workforce forecasting, and training to ensure a consistent "white-glove" experience.

• Serve as the founding regional hire for the Singapore support team, leading the local expansion and recruitment efforts. • Build and establish Tailscale’s company culture and operational standards within the new Singapore region. • Manage day-to-day support operations for a pod of 8-10 Tier 1 and Tier 2 Support Engineers. • Lead the hiring, onboarding, technical mentoring, and career coaching for all direct reports in the region. • Coordinate in-office time to foster team collaboration, establish the local office environment, and support new hires. • Oversee the regional support queue to ensure SLA/SLO adherence, focusing on APAC specific tickets and partnering on global queue health. • Act as an internal escalation point for both complex technical issues and difficult customer situations. • Partner with the VP of Customer Engineering to align regional team outcomes with the broader global strategy. • Analyze regional support data and customer feedback (CSAT) to surface trends and insights to leadership. • Refine support workflows and internal tooling in collaboration with Support and CX Operations. • Conduct regular quality assurance reviews on tickets to maintain high technical accuracy and a consistent brand voice.

• Manage, coach, and develop a team of 5 to 10 CS Quality Associates across multiple regions • Drive team performance through clear goal-setting, regular feedback, and structured development plans • Foster strong engagement, accountability, and high performance standards within the team • Own QA performance metrics and reporting, ensuring accuracy, visibility, and actionable insights • Continuously evolve the QA framework, including evaluation rubrics, methodologies, and calibration processes • Identify trends and gaps in quality performance, translating insights into prioritized improvement initiatives • Ensure alignment and consistency in QA standards across US and EU operations • Adapt processes to effectively support a globally distributed team while maintaining high standards • Partner with BPO vendors to ensure quality expectations are clearly defined, met, and consistently applied • Collaborate with cross-functional teams to drive continuous improvement initiatives • Use QA insights to influence decision-making and enhance overall service delivery and processes • Own forecasting of QA evaluation volumes based on contact projections and quality coverage targets • Ensure the QA team operates efficiently by balancing evaluation output, quality, and cost