Pickyourtrail: Featured Business Of The Week

1. Please tell us more about Pickyourtrail’s founding story and how you have built it up to where it is today?


Founding Story:

Pickyourtrail began as an attempt to break how vacations are currently been planned and booked by travelers. At our very heart, we want to create happiness and not sell packages. The seed to all this began in August 2012 when we went on a Europe trip (me and Srinath Shankar).


Ardent travelers ourselves, we had put in more than 2 months to fully craft the vacation. This included planning end-end, bookings, and visa processing. It was during the trip we stumbled upon fellow travelers who were all on packaged tours. Interacting with them, we understood they were literally rushed between destinations and their urge to discover new experiences wasn’t fulfilled. The travelers, on the other hand, were amazed to see the flexibility we had in our itinerary and that piqued their interest.


Once back home, we were bombarded with pings asking for details on how they went about planning the entire trip. These interactions slowly multiplied and this lead to an idea that will forever change our career roadmaps!


How you have built it up to where it is today?


Interacting with our initial customers, we realized that planning an entire vacation is quite a hassle. People hop 38 sites to create an itinerary and then book using 11-13 sites. If they work with the normal tour companies, the itineraries are quite “constraining”. There is no real personalization and you are basically “toured” from one place to another.


We wanted to build a self-service platform for international vacations. Great care goes into replicating the adrenalin rush and satisfaction of self-planning. At the same time, it ensures that while technology does all the heavy lifting – personalization, curation, real-time pricing, instant booking, on trip recommendations etc. The end goal – to give you that hassle-free international vacation that you worked so hard for.


2. What are your plans for this capital raised, and how have you been achieving your goals?


Broadly 3-4 things we wanted to do with the funding, one obviously acquire more customers on the digital medium, try and build you know our own digital acquisition channel that’s number 1.


Number 2 is you know on tier 2- tier 3 towns where digital penetration is still not very high but still there is a significant amount of people taking trips out there, how do we go to that audience and become top of mind for that audience, So if you look at it audience wise the digital first audience is what we want to capture and then tier 2- tier 3 towns


The next focus is on beefing up the tech team and overall tech capabilities. How do we ensure that our product innovation efforts continue to be one of the best in the industry?


There is also a larger focus on taking this product global. End of the day there is a European going to the US  or an Australian going to Bali and the product is suitable even for them. We also want to try and understand what it takes to build traction in those markets.


While all this may not be possible in the next 6-10 months but this is the broad themes we want to focus and kind of drive over the next 2-3 years.


How have you been achieving goals?


Rigour, Industry knowledge and belief in our team 🙂


3. How does Travel Industry specific ecosystem looking like at the moment and how does this compare to a few years ago?


  1. In the early 2000s, flights went online and people became comfortable booking them online. Last 10 years same evolution has happened for hotels. We are betting on the fact that vacations will also go online if we solve the holy grail of self-serve platform which gives – best price, wide variety of options and contextual information about a place.
  2. India is getting connected to the world at a rapid pace like never before. The no of countries connected directly from India has grown significantly. There is already a convergence of sort happening where fares to SEA (Southeast Asia) from India is comparable to flying within India.
  3. Indians are planning international vacations which are not group tours. Access to better income, willingness to spend and brag-worthy status of international holidays are the catalyst to this behavior.

4. What are the biggest challenges facing the Travel Industry and what do you think it will look like in 5 years’ time?


If you look at vacation space I’m going to define the industry as you know just the trip packaging or the vacation packaging space.


I think broadly there are 2 or 3 challenges;

1- Lack of customization ie., that is if you work with any OTA it takes 24 to 48 hrs to actually customize your itinerary. So people have to wait in order to build their own customized personal itinerary is a significant challenge;

2- Self – Planning: If you think of planning everything on your own then people will have to hop about 40 – 45 sites to put together a plan of pricing, routine and logistics of the travel, so self-planning is a big challenge in itself.

3 Trust Building: It is a very involved purchase in very little amount of time and how do you build trust and ensuring that information overload does not get to people. Those in our mind are some of the challenges that the industry has and I’m not even talking about trust or you know or overcharging, those things I think continue to exist and I think the whole idea of online is the transparency is built in.


5 Years down the line – more self-booking platforms would be a trend, more tourism boards promoting

Their countries and travelers trend for international bookings always on an upward curve.


5. What is the biggest lesson you have learned as a founder?

Srinath Shankar, Co-founder: – Risk taking can be science. Risk taking is a culmination of gut feel which is nurtured through building enough context in the industry you work in.


6. What’s the most important thing you’re working on right now, and how are you making it happen?

Srinath Shankar, Co-founder: – Product innovation will continue to be our core focus for the coming 12-18 months. There are few internal pilot projects which are solely aiming at giving our customers a superior experience in terms of price discovery, contextual information at the right time and ability to simplify decision making for vacation planning.


7. Take me through the skills of your top team members. What is each person best at?

Srinath Shankar, Co-founder – We have been lucky with people. What our rockstars bring to the table is a passionate commitment. Over the period of last 5 years, we have had people who are good at execution, building scalable processes, multi-tasking and thinking innovation first from a product perspective.

8. What’s the hardest decision you’ve made so far?

Srinath Shankar, Co-founder– Saying no to customers who are not our target audience. We are in the space of catering to Leisure holiday travelers and this has meant saying no to MICE segment(meetings, incentives, conference, exhibitions). We have always been clear about what we are good at and what we do not do.


9. What does culture mean to you and how do you ensure this culture is maintained with everyone at the company?


Culture to us is more than just a list of values or beliefs. It is a way of work. We believe with a strong culture the people are empowered to ask the right questions and act in the best interest of their customers and co-workers. Great culture is crucial to both attract and retain talent in this day and age.  If you ask how we do it? It’s simple – We have a separate round called culture round as part of our interview process to assess whether the candidate would enjoy the culture at Pickyourtrail.

10. What are some industry trends that are driving the company’s strategies for future growth?

  • Cheaper airlines
  • Direct connections
  • Suppliers embracing tech
  • Online bookings of big-ticket

11. What is the company’s competitive advantage? Why will it be sustained?


Pickyourtrail’s proprietary comfort score algorithm takes into account over 40 factors like duration, travel time, ratings etc to build personalized itineraries that travelers can further customize & book. Post booking, travelers use Pickyourtrail’s app to not just keep track of bookings, but also get real-time information on flight and weather updates, restaurant recommendations and on-trip chat support. We are solving a problem that currently nobody in the industry is, we have a head-on in giving hassle-free vacations online with as much speed as possible.



12. What do you do when you’re not at work?


Work. Jokes apart, travel and time with family and friends is something we take time off for.


13. Last but not least what would be your advice to all those budding entrepreneurs?


Find out what drives you, what is your true north and act on that. While its easier said than done, being true to who you are as a person, is key to success in your entrepreneurial journey.


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