Dose #111: Subscription Tips from a CTO

Tried and True Tips to Maximize Subscribers

Matt here with your weekly Subscription Prescription 💊

Ever wonder what features you need to make subscriptions successful? Or how you can maximize the value of your subscriber base? This week we take insights from a talented CTO about how to grow subscriptions. We start with 3 tips to focus on subscriber value, and then 3 tips to increase subscriber LTV.

This week’s dose is also an hour-long interview with Ben Fisher, a talented and accomplished CTO in the Shopify ecosystem. Listen to this insights during the full interview on your favorite platform:

Changing the Game in Loyalty

Is your loyalty program inspiring customers to engage with and buy more from your brand?

In a world where points programs miss on what your customers want and need, Upzelo is changing how you engage with them.

Upzelo is a customer loyalty, referrals, and rewards platform designed for online and retail stores. They’re building something special that focuses on how customers shop, refer, and pick winners for their repeat business.

Take a moment and check out their platform to see something different in the loyalty space!

What is both enabling and frustrating about e-commerce is the technology. At any given time, tech is making purchases easier, but implementing and building it can be a nightmare.

That’s why Shopify has come to dominate the ecom landscape; they’ve done wonders at making tech more accessible through their platform and app ecosystem.

Knowing what to build and how it will enable greater profitability for your business is difficult and expensive. So that’s why for this week’s dose I’m going to share some key insights from a good friend: Ben Fisher.

Ben is a fractional CTO to a number of brands and has built tech used by brands like Athletic Greens, Earth Breeze, and Biom. He’s built (and sold) numerous tech companies like Carthook, and Rodeo.

To put it mildly, Ben knows subscriptions. While you can grab the full interview from one of the links above, I’ve taken 6 simple ways he shared to improve subscriptions.

Understanding Your Subscription Landscape

Whether you’re evaluating a new subscription app or just trying to figure out the one you’re on, you’re probably wondering what tech you need.

Key Takeaway: Focus on what your subscribers truly value.

Keep these points in mind when evaluating what you need now or will need in the future.

  1. Evaluate Actual Needs: Assess which features are crucial for your business by reviewing support tickets and customer feedback over the last 90 days. Create a list of must-have functionalities and discuss these with potential vendors.

  2. Avoid Feature Overload: Many brands get caught up in the feature wars. Focus on features that have a direct impact on customer experience and retention. Make sure you’re enabling the right actions while keeping it simple overall.

  3. Customer-Centric Approach: Always think from the consumer’s perspective. Are the tools and features truly enhancing their experience? Is this something they’re actually using?

Reviewing support tickets and customer feedback will show you the right path forward. Sometimes this means turning off features that are harming user experience or building something new to make it easier.

Driving High LTV and Contribution Margins

You’re already working hard to keep people on a subscription longer by reducing churn. But what are you offering subscribers to improve LTV and profitability?

Key takeaway: Upsell Annual Subscriptions

Some simple methods to improve average LTV:

  1. Upgrading Monthly to Annual Subscriptions. Post-purchase upsells are a powerful strategy. Convert monthly subscribers to annual ones by offering attractive discounts. This approach boosts your cash flow and reduces churn.

  2. In-Cycle Upgrades. Present an annual upgrade offer 14 days into a monthly subscription cycle. This capitalizes on the customer’s initial excitement about the product. You can test this at different times, like to subscribers that make it to the 4th or 5th cycle.

  3. Simplified Subscription Management. Ensure your subscription portal is user-friendly. Eliminate unnecessary steps like password logins to reduce friction and improve customer satisfaction. Any time a customer can make a quick change without friction is a win.


One of the most impactful opportunities for any subscription brand is to focus on what customers want from you. This makes it easier to know what tech to buy or build for your brand.

You can also improve subscriber value by offering annual subscriptions. This allows you to capture more revenue up-front and guarantees you’ll have a customer for the next year.

Keep focused on what your customers want and offer great value to those who want to stick around.

That’s it for this week! Stay tuned for next dose #112 out next Tuesday.

 - Matt Holman 🩺

The Subscription Doc