Founded in 2019, Headway is a global edtech startup with Ukrainian roots. They make learning easy, fun, and accessible through bite-sized, on-the-go learning experiences. Their flagship product, the Headway app, is used by more than 15 million people in 35-plus countries, featured in the Apple App Store and Google Play stores, and top 10 in the education category.

With Headway, users decide how they want to learn—through video, audio, or text—and what they want to learn, based on their self-growth goals, such as productivity or leadership hacks. Subscribers can use it throughout the day, like while getting ready, commuting, waiting in line for coffee, etc. There’s a gamification element to the Headway app as well, which allows users to set goals based on their quest for new knowledge and skills, track progress, and collect achievements. 

As Headway emphasizes, “Enjoy the fun, fully customized journey of learning!”

In a Mobile World, Single-Channel Communication Misses the Mark

As an app-based platform, Headway understands that mobile channels are the best avenues to reach repeat and new subscribers. Last year, they recognized that using an email-only platform limited their opportunities to reach and engage a vast number of mobile-inclined customers, and resulted in these marketing limitations: 

• They lacked powerful tools such as advanced segmentation, AI, and A/B testing to streamline the end-to-end lifecycle management process and improve marketing activation, creation, personalization, scale, and impact.
• Their previous Email-Service Provider (ESP) wasn’t built for data—that meant an inability for Headway to unlock key information which influences more customer-centric communications across multiple channels.
• An inability of the ESP to integrate with existing tool stacks (e.g. Amplitude and AppsFlyer) meant fewer advanced data application possibilities like richer customer insights.

By depending on an email-only platform, Headway couldn’t deliver cross-channel communications to different audiences, at certain times, including unique content that resonates with each subscriber and supports their quest for knowledge and self-improvement.

Getting Ahead, With Iterable

In May 2022, Headway switched to Iterable and they haven’t looked back. They found joy by having one solution with an intuitive interface and wide-ranging features, such as robust segmentation, a flexible data model, and machine learning. With Iterable Headway can create unique, timely, cross-channel communications that forge deeper customer connections for better brand awareness, satisfaction, and loyalty. 

As the latest addition to Headway’s marketing toolkit, Iterable also helps them to “maintain balance in the type of communications users receive, and how often, which is essential to stay more reactive to users’ wide-ranging activities, behaviors, and desires to enhance their knowledge and skills,” said Zarubina.

Now, Headway can effectively segment subscribers according to behavioral and user data like how often they use the app or whether they have a subscription, and send emails, push notifications, or both—a benefit that wasn’t available less than a year ago. This has especially impacted Headway’s onboarding experience.

A Better Onboarding Experience With A/B Testing, AI, and Journeys

Freemium and premium users are both important to Headway’s business objectives. They make up their evolving customer base, but have different behaviors. Freemium app users may hesitate on purchasing a premium subscription. Meanwhile, premium users don’t always use the app consistently or for a long period of time.  

The first week after signup is the most important for the lifetime value of Headway users because this is when they are getting acquainted with the product and deciding on a subscription purchase. With this in mind, Headway’s marketing team created a journey using Iterable Studio for someone’s first week on the app. The flow for the journey has two paths for freemium and premium users. 

• For freemium users, communications convey the app’s benefits, show how flexible and easy it is to use, and entice them with offers so they opt to become a premium subscriber, and eventually see how this option meets their needs. 
• For premium users, communications emphasize reasons to continue using the app. For example, it has interesting features like gamification, plus a wealth of resources and curated collections available in multiple formats, but only found in Headway. The messages emphasize the different ways to use the app for lifelong learning.

Taking this approach to better connect with both groups of users, Headway hopes to keep all of their users engaged by habitually using the app, and ultimately convert freemium users to premium subscribers. By having access to user data in Iterable, like a user’s educational interests, and behavioral data, such as the actions a user is taking in the Headway application, they can better segment their audiences and increasingly personalize communications throughout the user lifecycle. With Iterable, they can also add event checks to a journey to see if someone makes a purchase or opens a specific message, for example, or include exit rules that remove someone from the journey based on a certain action or attribute change. 

By sending more personalized messages based on user data and using features like exit rules, Headway has avoided overloading someone with irrelevant notifications, created more opportunities to deliver useful advice that makes the app stickier with its users. These personalized messages have also supported more click-to-purchase, and freemium-to-premium subscriber conversions.

Fast, Comprehensive A/B Testing Improves Performance and Conversion

Headway appreciates the ability of fast, comprehensive A/B testing using Iterable’s experiment builder, which reassures them that they deliver the right messages, at the right time, through the best channels as people are introduced to the app. Previously, it took them more than a week to launch a test, but they launch them in a matter of minutes now.  

In their onboarding journey, they’ve tested different email subject lines or the call-to-action (CTA) in the email body. They recently ran A/B tests on three different subject lines for their welcome email with the goal of improving engagement and conversion to purchase:

1. Let your growth begin 💪 
2. Learn in less time with Headway! ⏰ 
3. So nice to meet you 💙 

The third subject line test result was the winner with a 46% email open rate (OR), contributing to an overall OR lift of 14%, an increase in click-to-open rate (CTOR) of almost 3%, and conversion to purchase increase by 2.3%. 

Iterable’s testing capabilities help them learn what resonates with users, and what doesn’t, so they can modify existing campaigns or execute new ones that generate lasting impact and positive results.   

AI-Driven Features Create Meaningful Subscriber Experiences

Headway leverages Iterable’s AI Suite within their journeys, including Send Time Optimization (STO) that uses machine learning to analyze historical engagement behavior and select an optimal, per-person send time for email and push messages. In fact, applying STO in their journeys has resulted in an average 7-9% increase in email open rates. They also concluded that the best time to send communications is late in the morning in a user’s time zone. 

Another AI feature, Brand Affinity™, automatically labels each individual user within Iterable according to their level of engagement with the brand. Headway is using Brand Affinity to test sending specific offers only to their engaged freemium users in an effort to convert them to paying subscribers.

Finally, Headway plans to begin using Predictive Goals to identify segments of users who are likely to convert on their business goals of monetization and retention. It might involve sending personalized messaging to segments who are “most likely to complete their next challenge” within the app to excite them to do. For example, if someone is interested in learning to boost their productivity, Headway might follow up with a list of book summaries and challenges about productivity.

Improved Onboarding Journey Lifts Open Rates and App Purchases

Thanks to the combination of Iterable’s robust segmentation and cross-channel capabilities, A/B testing, and AI Suite, Headway has experienced the following results:

• The OR with emails sent to freemium and premium users increased by 12%, on average, and nearly doubled with push notifications. 
• Conversion to purchase from clicks in personalized emails for freemium users increased by 2.4%, on average. 

Conversion to purchase from opening push notifications for freemium users increased by 1.3%, on average.

Across emails and push notifications, they will continue to test, analyze, and measure average opens, clicks, conversion to purchase, app metrics like challenges completed, and unsubscribes. They’re focused on continuing to improve customer engagement, monetization, and retention with Iterable’s help, too. Going forward, Headway plans to add in-app messaging as another avenue to target and engage with their 15-million—and growing—customer base. 

 “We hope to send even more events from the app and use them to segment users by behavior. We’re also building logic for the recommendation system conditions in the app so users can receive more personalized content, powered by Iterable,” concluded Zarubina. 

There’s abundant opportunity ahead, and if they experience any challenges along the way, Headway knows Iterable will provide partnership, problem-solving, and collaboration to strengthen their communications, user experience, brand reputation, and LTV.