TripCase User Engagement Email Program


While TripCase had millions of active users, their actual activity was low – engagement was virtually non-existent outside of a trip, and a huge percentage of users only used a small percentage of features.


Built an email engagement program from scratch, including accessing the right data and delivering valuable, helpful, personalized emails to our travelers.


– 10 trigger-based emails
– 750K weekly sends
– 27% average open rate
– Measurably changed user behaviour

The Situation
As one of the leading mobile travel apps, TripCase had millions of active users. However, a huge percentage of those users only used the app or logged into our website just before or during a trip. This created two key problems:

Problem: Big Opportunity for Churn Among Most Valuable Users
Our most valuable and loyal users might only travel once a quarter or so – thus leaving lots of time between trips, where they would often need password resets to get back into their account, be unaware of helpful new features, or possibly even begin researching competitors. We needed a non-intrusive, valuable way to engage with these travelers when they weren’t traveling.

Problem: Low Engagement Starves Product for Insights
While our product team conducted user feedback surveys, focus groups, and other research to drive their aggressive roadmap of new features. Additionally, for a large percentage of our users, their flight information would automatically be added into their account, but other data such as hotel reservations, car rentals, meetings, and more were an afterthought. This was a problem because they were missing out on great features that needed this extra context to shine, such as a one-click “Get an Uber” button that needed to know where you were going (to your hotel or a meeting) in order to provide value.

The Solution
Since we knew we had a valid email address for all of our users, that was an obvious choice to begin building a path to having an ongoing relationship with our travelers, unrestricted by whether or not they had a trip coming up.

I began to sketch out a map and timeline for the profiles and scenarios that we had identified to begin having that connection to our travelers, specifically focusing on trigger points where we could have a contextual opportunity to help them engage with us without being obnoxious.

We created 10 emails, each specially designed to be easy to update and to use the data we had for each individual traveler to ensure it was personalized and non-intrusive.

  • Release Newsletter – timed along with our ~monthly app updates, to highlight new features and capabilities that our product team had delivered
  • Introduction – for new users, to roll out the welcome mat and affirm their decision to sign up by highlighting key features
  • App Install – delivered to users who hadn’t installed our mobile app, to showcase the benefits of having TripCase right on their phone (such as real-time flight alerts that our competition charged for)
  • Anniversary – a special email delivered annually to thank loyal users and highlight some fun stats about their travels
  • Winback – for users who hadn’t accessed their account in a while, to inform them of features that had been added since their last login and welcome them back
  • No Trips – a wanderlust-oriented email to spark inspiration and showcase exciting/relaxing places they might like to visit
  • Pre- and Post-Trip – centered around a trip, to share ways that TripCase could make their trip easier, or to welcome them home and provide easy access to stored receipts/etc.
  • Missing Other/Hotel – sent before the trip, for travelers who had only added a flight, to showcase the benefit of keeping all of their travel details in one single place, and highlight the cool ways we could then help them travel smarter.

The Results
Within 12 months, I was sending ~750K emails per week (not including the newsletter), with an average open rate of 27% and maintaining an unsubscribe rate of <1%.

Additionally, the action-oriented emails were successful in changing user behavior. Prior to having this system, over 60% of our trips were “flight-only” – this dropped to 40% within 12 months. We had also previously seen that travelers typically added their hotel information only 10 days prior to their trip starting (despite adding their flight 2 months before, on average). We sent the “Missing Hotel” email at 12 days prior to their trip starting, and within 12 months, the average time between hotel add and trip start had risen to 11.6 days.

3 Keys to Success
1. Plan to scale
– when I realized that I would need new emails built, I worked with a talented agency to provide a few templates that I could then customize on my own, as opposed to custom designs. Not only was this more cost-effective for the overall project, but it allowed me to quickly and easily build new emails along the way as needed, without needing ongoing support.

2. Make data-driven decisions – determining the best triggers and timing for these emails was crucial for their success. I worked closely with the product team and our data and analytics team to understand the behaviors of our current customers. This data made it easy to decide when to send these emails to our travelers to best serve them and provide value.

3. Know what you’re measuring – by establishing KPIs early on in the project, I was able to quickly assess whether or not the project was succeeding at its core goals. Looking at email-specific metrics, such as open rate, clickthrough rate, and unsubscribe rate is important, but it was also critical that I worked with our product team to be able to see if the emails were actually changing user behavior.