Achieving Mission & Profit with Freemium — Erin Webster-Shaller and Paul Apollo, Lose It!

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On this episode: balancing mission and monetization, the challenges inherent to referral programs, and why Lose It! had to abandon a big push into paid user acquisition.

Top Takeaways

🆓 Excellent free products need a large user base to upsell — messaging millions of users about special offers can deliver fantastic returns. (10:32)

🚂 Extend onboarding for increased trial engagement by asking more personalized questions to boost trial start rates and tailor the user experience. (14:43)

👏 Celebrate user success to drive word-of-mouth marketing and organic growth, while strengthening the bond between users and your brand. (25:47)

🥇 Encourage setup of premium features during trials while carefully A/B testing each feature for user resonance. (31:49)

🏃 Identify key actions to boost user conversion with the power of data analysis: Target users with discounts or special offers to entice them to upgrade to a premium subscription. (36:29)

About Erin Webster-Shaller

👨‍💻 VP of Marketing at Lose It!, one of the first health and wellness apps on the App Store.

💪 Erin has been responsible for determining whether new features should be premium or free, as well as running A/B testing for messaging.

💡 “There’s a lot of gimmicks in the weight loss industry: We try to be authentic and real with what this product can help you do — but also not oversell it [and] promise something that isn’t realistic.”

👋 LinkedIn | Twitter

About Paul Apollo

👨‍💻 Senior VP of Operations at Lose It!.

💪 Paul has been with the company for nine years and has spent nearly that entire time in growth marketing.

💡 “We want to make sure that there is an excellent free product available for anybody who wants access to it.”

👋 LinkedIn

Links & Resources

‣ Check out Lose It!

‣ Work with Lose It!

‣ Connect with Erin on LinkedIn

‣ Connect with Erin on Twitter

‣ Connect with Paul on LinkedIn

Episode Highlights

[1:45] Mission-driven: Lose It! founder JJ Allaire was tracking calories on a spreadsheet when the App Store was born. Increasing satisfaction for happy users aligned perfectly with the app’s growth.

[6:18] No monetization: The app went from being totally free to freemium. The team didn’t even dabble with ads until very late in the game.

[7:28] Buying out Series A investors: Lose It! was so profitable it became fully founder- and employee-owned when it was acquired in 2022 by Ziff Davis.

[9:22] The feature adoption journey: The team doesn’t test locking features, but they do A/B test messaging and positioning. Apps and Devices is a big crowd-pleaser, Paul explains.

[14:02] Loss aversion onboarding: When Lose It! noticed inexplicably longer onboarding, they tested with more questions, which snowballed into significant success. Adding premium features to onboarding didn’t have the same effect.

[20:58] 135 million-pound loss: 50 million users came primarily from consistent word-of-mouth growth and organic acquisition. Experimenting with paid acquisition in 2019 didn’t work out.

[25:47] Pushing word of mouth: Erin explains how the company gets people to “spread the good word” to lose more, although experimentation showed that referrals aren’t a silver bullet.

[31:49] Lifecycle messaging: Paul jumps into the strategy of exposing freemium users to premium and keeping premium users engaged.

[38:07] In-app messaging: Lose It! experimented with in-app messaging versus email blasts.