About Pickyourtrail (PYT)
Pickyourtrail (PYT) is an expert co-creator of super hit customised holidays. We are the perfect partner to the ‘designated travel planner/s’ of every group - big or small. Our service, customisation and expertise help us deliver super hit holidays and make the planner the hero of the holiday.
The mission is simple: to make customized international travel easy, reliable, and uniquely memorable. Candidates are invited to join the team in shaping the future of global exploration!
Why work with Pickyourtrail?
Pickyourtrail is one of the very few travel startups that has not only survived the pandemic but have significantly expanded, increasing our product portfolio to now include domestic staycations and global markets in addition to our India outbound market.
Despite the tough circumstances surrounding the pandemic, we have managed to maintain and, in fact, grow our Glassdoor rating to 4.2 out of 5.
Key benefits:
High Impact Opportunity
Leisure travel is on a major uptick, much like online meetings were in February 2020. This presents a unique opportunity to utilize your experience to accelerate the organization's growth and achieve desired objectives.
Growth:
Work alongside seasoned travel entrepreneurs and marketers, gaining invaluable experience in a high-growth sector
Autonomy & Ownership:
We empower our team members to take full ownership. You are responsible for the full, end-to-end execution of all strategies and the delivery of measurable results.
Role Brief
At Pickyourtrail, we don’t just plan trips—we craft experiences people remember for a lifetime. And this role sits right at the heart of that.
We’re looking for someone who can own the customer journey end-to-end, lead our on-trip support like a pro, and build a team that truly puts customers first.
What You’ll Own
1. End-to-End Customer Experience
Design and continuously improve the entire customer journey—from trip planning to post-trip engagement
Build strong feedback loops and turn insights into action to improve NPS, CSAT, and retention
Work closely with sales, product, supply, and tech to ensure a seamless experience across touchpoints
Own escalations and negative feedback—drive quick resolutions and long-term fixes
2. On-Trip Support Excellence
Lead the concierge team delivering 24/7 real-time support to travelers
Ensure customers feel supported, informed, and cared for throughout their trip
Train and enable the team to handle high-pressure situations with confidence
Drive proactive communication and structured winback strategies for unhappy customers
3. Team Leadership & Culture
Hire, mentor, and manage high-performing CX and on-trip support teams
Set clear KPIs and performance standards
Build a culture of customer obsession, accountability, and continuous improvement
Identify and groom future leaders within the team
4. Data & Continuous Improvement
Use customer data and feedback to identify gaps and improve experiences at scale
Track trends, recurring issues, and fix systemic problems proactively
Partner with product and tech teams to improve tools (app, CRM, automation)
Bring a strong data-driven mindset to every decision
Who this Role is perfect for
3 - 6 years in Customer Experience, Travel operations, or Concierge Services
Minimum 2+ years managing teams in high-intensity, customer-facing environments
Strong track record of improving CSAT/NPS and handling escalations
Someone who thrives in real-time problem-solving and crisis situations
Highly data-driven, but equally people-focused
