Headway's Web Funnel is Brilliant
Welcome to another episode of Fix That Funnel. Today, we're breaking down the web funnel of Headway, one of the biggest apps in the learning and self improvement space. With its bite sized books and huge learnings, Headway is the go-to app for anyone looking to grow their brain without having to dedicate the time.
But how smart is their web2app strategy? To find out, we're enlisting the help of Jacob Rushfinn, founder of Retention.blog, to explore what’s working—and what could use some improvements.
Still want more? Check out the full interview with Jacob Rushfinn, exclusively available on Paddle Studios.
Web2App Strategy
Headway supports a hybrid funnel strategy — users can purchase on the web or via the App Store. This approach is becoming increasingly common:
- Escape App Store Limitations: With Apple’s privacy restrictions making attribution harder, web-based funnels allow for more transparent user data and better ad optimization.
- Unlock Additional Ad Inventory: Web funnels open up new ad channels, making campaigns more scalable and cost-effective.
- Flexibility in Payment & Pricing: Web also allows Headway to implement custom pricing, testing strategies, and friction-reducing UX decisions not always possible inside app store constraints.
In other words, web provides more control — over data, pricing, and growth levers — especially useful for a global subscription business like Headway.
Onboarding
Headway’s onboarding stands out as one of the most comprehensive flows this season.
- Immediate Entry Point: Users are hit with a simple “Become the most interesting person in the room” headline and then immediately asked an easy question (e.g., age). This low-friction intro helps build momentum and reduces bounce.
- Layered Social Proof: As users move through the flow, Headway introduces press mentions and user testimonials. It’s not overwhelming — just enough to build trust as you proceed.
- Push & Pull Experience: The onboarding alternates between asking personal questions and providing reassurances. For example, if users indicate they’re struggling with finances or productivity, Headway affirms that the app can help. These contextual empathy cues are a great UX touch.
- Emotionally-Tuned Interactions: The text box responses — small but thoughtful flourishes that guide the user through more sensitive moments with care.
- Progress Indicators & Buy-In: Headway uses progress bars and “yes/no” questions near the end to increase perceived investment, nudging users toward conversion without applying overt pressure.
- Desktop vs Mobile Differences: On desktop, users tap through screens one-by-one; on mobile, they scroll through book options. This demonstrates how Headway adapts UX per platform, something many apps overlook.
Long onboarding flows work best when the goal is to drive higher-priced conversions — and Headway uses it effectively to build trust and justify their pricing.
Paywall
After onboarding, users land on the paywall. It offers three subscription tiers.
At first glance, this looks like a value-driven layout — but some clever pricing psychology:
- Strategic Anchoring: The “3-month” plan is subtly framed as the best deal and likely chosen to maximize average revenue per user (ARPU) without long-term commitment.
- Manipulative? Maybe. Effective? Definitely: While the 12-month plan may look like a better long-term deal, the immediate renewal risk can scare users. A 3-month plan feels like a “safe middle ground.”
- Auto-Renewal Nuances: The 12-month plan auto-renews at $100 annually — not everyone will notice this right away, which may lead to accidental retention (and revenue).
Pricing strategies are worth testing — what feels slightly manipulative may actually drive higher satisfaction if value is delivered.
- Local Currency: USD in the U.S., Euros in the EU, etc. This small but vital move reassures users they’re buying something built “for them.”
- Region-Specific Pricing: Adjusting actual prices by region accounts for differences in purchasing power. $10 in the U.S. doesn’t translate to the same value in India or South America — so smart localization improves access without sacrificing LTV.
While not every option is available, Headway offers a solid set of payment methods.
- More Is Better — To a Point: Offering Apple Pay, Google Pay, PayPal, and others increases conversions, especially when users hesitate to enter card details.
- Balance UX With Feasibility: It’s hard to integrate and maintain multiple processors unless you’re using a platform like Paddle — but doing so can be a revenue unlock.
- Audience Segmentation Matters: Younger users often prefer mobile wallets. Older users tend to stick with credit cards. Knowing your demographic helps prioritize.
Download Friction
After purchase, Headway encourages users to download the mobile app via two buttons: Google Play and App Store. While better than nothing there is some room for improvement:
- Add a QR Code (Especially for Desktop): This makes the transition effortless.
- Email Reinforcement: Send a download link to the user’s inbox immediately after purchase.
- Platform-Aware Nudging: If the user is on desktop, show extra encouragement to switch platforms. If on mobile, consider in-app deep links.
The goal is to make sure the user journey continues smoothly — no matter where it started.
Takeaways
What Headway Does Well:
- Frictionless First Steps: The onboarding begins with easy wins, drawing users in quickly and building commitment.
- Thoughtful Personalization (Emotionally and Visually): Green text cues, social proof, and sensitivity around question tone create a high-trust environment.
Where They Could Improve:
- Deeper Personalization Based on Answers: Users answer multiple detailed questions, but the resulting experience stays the same. Dynamic flows or personalized content suggestions would close that loop.
- Stronger Web-to-App Handoff: Adding QR codes or surfacing download emails more prominently could boost mobile engagement post-purchase.
Thanks to Jacob Rushfinn for his expert insight, make sure to check out Retention.blog where Jacob does his own teardowns and writeups.
Next week, Fix That Funnel gets limber with Asana Rebel.
00:00:02:21 - 00:00:29:02
Steve
Doctor Lecter. You make me laugh. Oh hi. I didn't see you there. Welcome to fix that funnel. I am your host, Steve. And today I am back in my beautiful study to break down headway. Now, I am an avid book collector, as you can see, and it would take me years to read everything in my library. That is where headway comes in with headway, I can gain all the knowledge from my library and a lot less time with summaries catered to my interest generated just for me.
00:00:29:08 - 00:00:49:12
Steve
Now headway has an awesome product, but is their web app strategy as good as that product? Today, with the help of an expert, we're going to break it all down for you to show you what they're doing well and not so well to help steer you in the right direction. So are you ready to fix that funnel? We're going to fix that funnel tonight.
00:00:49:12 - 00:01:02:16
Steve
We're going to fix your funnel. Right. We're gonna fix that funnel tonight. We're gonna make those prospects buy. Doesn't matter if you're big or small. We're gonna fix your onboarding. And meanwhile, we're.
00:01:02:16 - 00:01:03:14
Jacob
Gonna fix.
00:01:03:16 - 00:01:06:10
Steve
That funnel tonight. We're gonna fix.
00:01:06:10 - 00:01:14:15
Steve
That until tonight.
00:01:14:17 - 00:01:34:09
Steve
Well, Michael, I'd love to talk more, but I have a meeting with the bigwigs about our web two app strategy. Churn is on the Fritz. New payment methods pop up every day, and our customer base is global. But I didn't realize we'd have to deal with sales tax compliance. Sounds like a lot of stress these days. I'm stressing out more and more and more.
00:01:34:11 - 00:01:44:08
Steve
Wait, wait, did you say more? I'm sending you paddle right now. Their whole thing is giving the world more. Check your mailbox tomorrow morning with paddle.
00:01:44:11 - 00:02:00:21
Narrator
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00:02:01:01 - 00:02:13:14
Steve
Hey, Michael, nice to chat with you again. Yeah, yeah, I have a lot to cover. Is it okay if we go over? I know you've been busy with the whole web app thing. Michael. Michael, we have plenty of time. Have that all taken care of now.
00:02:13:16 - 00:02:18:11
Narrator
The world needs more. So why settle for less? Get started.
00:02:18:11 - 00:02:24:04
Steve
Now.
00:02:24:06 - 00:02:32:05
Steve
Thank you. Thank you very much. Hey, everybody. Welcome to fix that funnel. Today we have a very special guest from Retention Blog. Everybody welcome Jacob Rushton.
00:02:32:11 - 00:02:35:05
Jacob
Hey, thanks for having me. Yeah, really excited to chat.
00:02:35:09 - 00:02:39:00
Steve
So my first question, Jacob, how did you get into this crazy world of app growth?
00:02:39:01 - 00:02:56:22
Jacob
I started off more in the life cycle marketing world in terms of email push and all of that for the past couple of years had been doing consulting and advising, as well as writing, retention, dot blog, which has been a lot of fun to, to share all my insights and experience, with the world.
00:02:57:00 - 00:03:13:09
Steve
After this episode. Make sure to check out Retention Blog where Jacob actually broke down head way from front to back. But from now, let's check out their web two app strategy. So you can purchase headway on the web and also on the App Store. What are the benefits of running this hybrid strategy?
00:03:13:11 - 00:03:36:02
Jacob
All the Apple privacy restrictions, it became a lot harder to attribute data and optimize with web. You don't have those same limitations. And so not only can you improve the efficiency or performance of your ad campaigns, you can actually scale more efficiently. Or just scale more back up because you're opening up a new inventory.
00:03:36:04 - 00:03:41:18
Steve
So, Jacob, you're super knowledgeable on headways onboarding. What are some differences between desktop and mobile?
00:03:41:20 - 00:04:08:10
Jacob
I think the most obvious one is it's longer, often a longer web. Onboarding flow is important because there's higher friction on payment. And so you have to build up a little more investment, build up a little more excitement to convince users to pay. You should think about the clicking versus tapping or swiping. And so interaction styles and how you design the flow should be a little different as well.
00:04:08:11 - 00:04:16:18
Steve
So now that Jacob's given a breakdown of their web two app strategy as a whole, it's time to dive headfirst into their onboarding.
00:04:16:20 - 00:04:23:09
Steve
So, Jacob, when we start off headways onboarding here, we start with this big H1 right off the bat. What's the importance of this first page here?
00:04:23:11 - 00:04:40:08
Jacob
It doesn't give you a lot of context right. Become the most interesting person in the room. And then it just diving right in. These age question is so easy. It's just such an easy thing. The goal here just to get you to continue it, just to get you to start. And then once you dive in, they reassure you and try to build trust how you hey, you're in the right place.
00:04:40:10 - 00:04:46:19
Jacob
Everybody's doing it right. People are used to headway. Build trust through social proof, through press mentions.
00:04:46:22 - 00:04:52:22
Steve
So as we highlighted a little bit before, we see a lot of social proofing here. What's the importance of social proofing in an onboarding flow.
00:04:53:01 - 00:05:02:22
Jacob
I would say it's crucial. Usually it's very helpful. Sometimes it doesn't do anything. So it's not like a panacea, but generally it's, a nice thing to have.
00:05:02:23 - 00:05:08:06
Steve
So let's go back to that push and pull analogy as we keep going further down the flow. And we see more of that push and pull.
00:05:08:07 - 00:05:28:15
Jacob
Some of them have this, personalization. Look at the little green text box. This is a really nice touch. I like these reassurances based on questions that are a little more sensitive. So do you feel good about your finances? Can be a pretty emotional question, right? If you say no, this reassures you that they'll be able to help with that area.
00:05:28:18 - 00:05:38:22
Jacob
If you're asking tough or negative questions, think about how you can manage their emotions and make them feel better, while also showing the value of your product at the same time.
00:05:39:00 - 00:05:44:15
Steve
Now, this flow of headway is one of the longest we've seen this season. Why are they running such an extensive onboarding?
00:05:44:17 - 00:06:03:20
Jacob
Creating a better, better product experience is nice. Retaining customers is nice, but usually improves conversion. Usually that's the ultimate goal of getting someone more more boarded. One note on these is, books is that it's actually different in the app. Instead of having you tap through with this same flow. They actually have a scrolling kind of list of a bunch of books.
00:06:03:23 - 00:06:11:10
Jacob
It shows that sometimes, you know, your your onboarding flow and your mobile, experience can deviate.
00:06:11:10 - 00:06:16:14
Steve
So, Jacob, you know, this onboarding journey in and out, what are some other things we're seeing here before we wrap up?
00:06:16:16 - 00:06:30:23
Jacob
Progress bar is usually good. The longer people go through the flow, the more likely they are to finish these yes or no questions right before you ask someone to pay. Is this this extra little nudge to build up investment to build up buy in?
00:06:31:01 - 00:06:39:03
Steve
Now that we finished up our onboarding journey, it's time to pull out our credit cards and head over to the paywall. And.
00:06:39:05 - 00:06:46:03
Steve
So, Jacob, we wrapped up our onboarding journey and now we're heading over to the paywall. We start off with our pricing page. What are we seeing on the pricing page here.
00:06:46:05 - 00:07:08:03
Jacob
So one month say 51% three months save 60% 12 months same 50%. And intuitively, you would think that you would want people on the longer plan, but they have the most popular a three months. They clearly want people to go to this one. Actually, if you go click on the 12 months, this would renew at $100 at the end of the year.
00:07:08:05 - 00:07:22:00
Jacob
It's an interesting, a bit of manipulative of this three month period. You don't think about it as much or news. Every three months. It renews once you go, oh, darn. That's fine. I'm still using it. They've seen they get more money from this.
00:07:22:04 - 00:07:36:02
Steve
Now, we actually ran this page through a VPN. And notice that headways using localized pricing. If I'm in Europe, they're charging me in euros. If I'm in the U.S., they're charging me in USD. Our data even showed that most people were able to purchase headway in their native currency. What's the importance of localizing pricing?
00:07:36:04 - 00:07:54:16
Jacob
So there's two aspects that you touch upon, right? The currency. If I open this in the U.S. and I see it in pounds or euros, I'm going to go. This isn't for me. Then there's the localized pricing of actually adjusting. You know, $9 U.S. is not the same value as in India or as in Costa Rica or, you know, other countries.
00:07:54:19 - 00:08:01:22
Jacob
If you are a global company and you are targeting, users all over the world, it can make a big difference.
00:08:02:00 - 00:08:06:08
Steve
And last up on our paywall here. Payment methods, are they offering up enough payment methods here?
00:08:06:09 - 00:08:14:19
Jacob
Generally more payment options is better as it's a general rule. This is hard to do right to if you don't have a tool like like battle I guess.
00:08:15:00 - 00:08:21:21
Steve
And now that we've wrapped up our paywall, it's time to go from the web over to the app.
00:08:21:23 - 00:08:31:07
Steve
Ecosystem. So after we purchase headway, we're seeing these two buttons here. Get it on Google Play and download it on the App Store. But that's about it. How important is this last step here?
00:08:31:09 - 00:08:42:10
Jacob
It's never super easy and it's never perfect. QR codes plus email usually is the easiest and so you just try to do the best. It's possible with providing users options.
00:08:42:12 - 00:08:48:19
Steve
So now that we've wrapped up Headways web funnel, it's time for some big takeaways. What are two things that are doing really, really well here?
00:08:48:21 - 00:09:09:17
Jacob
The entry into the onboarding, almost the most important is getting people started super quickly. What is the super simple? Everybody can answer with one click. Just go in. And that's really great. They do an amazing job of alternating between the questions and, the motivation and and social proof and and never overloading you too much with questions.
00:09:09:22 - 00:09:14:08
Steve
And if you were to do another retrospective on headway, what are some improvements you'd want to see in 2025?
00:09:14:09 - 00:09:30:15
Jacob
One thing that would be cool is a little more real personalization based on the questions, maybe different flows showing you different things. You answer all these things, but your experience doesn't really change. And so I think that could be interesting. I think there's so many things you could do there.
00:09:30:19 - 00:09:40:04
Steve
Well, I want to thank Jacob Rushton for being here. Check him out on social and make sure you go to Retention Blog for a ton more breakdowns of apps like headway and a ton of other great stuff. Thanks, Jacob.
00:09:40:06 - 00:09:41:21
Jacob
Yeah, thanks, Steve. This is great.
00:09:41:23 - 00:09:55:08
Steve
Now, after all that work breaking down headway, I am tired, I need to relax, and I need to head back to my study. I want to make headway for being such an awesome product. I want to thank Jacob Rushford again for being here today. And I want to thank you at home for watching. Fix that funnel. Make sure you check us out next week.
00:09:55:08 - 00:09:59:08
Steve
Word breakdown. Asana rebel. Now I'm going to read something a little less scary.
