How I got here:

When I took over the growth team at Codecademy in 2018, I wanted to make the biggest impact that I could on the business. I spent a month reading all the core books on growth, listened to every podcast I could find on the topic, and studied how other companies had done it.

The team was super excited, we sourced ideas from everywhere, worked across the product without boundaries, and rapidly shipped A/B tests to see where we could make improvements. We waited with anticipation for the money to start rolling in...

And we failed completely.

Our work was too spread out and we weren't focused in the right areas. We'd see some small test work, but they were in parts of the product that didn't really matter. Because we had so many ideas, we wanted to test all of them, so we'd move on from good ideas too early so we could test new ones.

After a lot of trial and error, we learned where to focus and how to scale the business.

This work paid off, we 5x'd our ARR from $10M ARR to $5OM ARR and the company sold for $525M in 2021.

After the sale, I was reflecting on why we'd been successful and started to think about the lessons that we'd learned.

A friend asked me, if you were to take on that challenge again, how would I do it a second time?

This led me to start writing, which led me to advise other companies, which has allowed me to see that these lessons apply across multiple companies in a variety of industries.

What Actually Matters in Subscription Businesses?

What I eventually learned is that 5 core things really matter in a subscription business.

After you have enough product-market fit to determine that you have solved a real user problem, you should focus on the following areas:

1. Paywall & Pricing - What is the difference between your product(s) and how are you charging for that?

2. Purchase Funnel - How do users buy the product? Do they understand it and is it free from confusion, friction, and bugs?

3. Extending the LTV of your users - Once someone has decided to buy the product, how do you increase their value to you?

4. Payment Processing - How do you maximize the likelihood that you get paid from users who already purchased?

5. Churn Appeasements - Once someone wants to cancel, what can you do (ethically) to help win them back?

Additionally, we'll cover common questions that arise such as:

- To freemium or not to freemium? When is this a good idea and when is this a terrible idea?

- What type of trials, guarantees or other purchase flows work for your business?

- How much to discount annual plans? Should you offer lifetime plans?

- How long can you realistically expect users to subscribe?