Year-End Check-Up for Subscription Companies: 10 Questions to Ask Yourself Now

Your subscription model is working well, and you have a market cap reflecting your strong annual recurring revenue (ARR) to prove it. Still, don't rest on your laurels. Go ahead and toast your successful year—you've earned it!—but also take a few hours during the holiday quiet to audit your business and assess your opportunities and risks for 2020.

In some ways, transactional businesses have it easier. They know what to do next because there's always a new product to launch, or an unhappy customer to please, or a campaign to plan. Not so with subscription models.

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The life of a subscription business leader is marked by consistency and smoothness rather than abrupt projects and campaigns. It can be easy to just keep moving on autopilot. But markets can shift beneath our feet, and client needs can change in a blink. There are always things we can do better, and the end of the year is a good time to reflect on what they might be.

Here are 10 questions to ask yourself when planning for 2020:

1. ENGAGEMENT: Are my existing subscribers fully engaged? What are we doing to make sure that frequency, recency, and depth are strong?

2. ACQUISITION: Are new prospects finding our offer as compelling as they did last year? Five years ago?

3. PRODUCT ROADMAP: What new features do we plan to add as we move ahead? Have we taken customer requests into account?

4. BUSINESS ROADMAP: What do our best subscribers want that they might pay more for? What is possible now that we can offer that wasn't possible when we launched? How can new technologies and platforms help?

5. EXPANSION: What other customer segments could our offerings appeal to?

6. SUPERUSERS: Which subscribers go beyond just being good subscribers and actually contribute to the health of our business, perhaps as ambassadors, references, or focus group participants? How can we recognize them, encourage them, and create more of them?

7. EVOLUTION: Which subscribers are the costliest and most distracting, and how can we attract fewer of them?

8. COMMUNITY: What are the objectives of our community? How well are we achieving these goals?

9. SUNSET: What have we been offering that no one uses? How could we better apply our resources?

10. DATA: What have we learned this year about our business that we didn't know last year? What are we doing with it?

Just taking the time to sit down, get focused, and do this self-assessment can lead to revelations that change the whole trajectory of your business. They can set you up for an even better year in 2020.

Robbie Kellman Baxter

Robbie Kellman Baxter is the author of international bestseller The Membership Economy: Find Your Superusers, Master the Forever Transaction, and Build Recurring Revenue, as well as the upcoming book The Forever Transaction: How to Build a Subscription Model So Compelling, Your Customers Will Never Want to Leave (McGraw-Hill Education, March 2020). She is founder of Peninsula Strategies LLC, a consulting firm that helps companies excel in the Membership Economy and a subject matter expert on membership models and subscription pricing. Her clients have included Microsoft, the Wall Street Journal, and Electronic Arts. Over the course of her career, Baxter has worked in or consulted to clients in more than twenty industries. As a public speaker, Baxter has presented to thousands of people in corporations, associations, and universities. Baxter has been quoted in or written articles for major media outlets, including Harvard Business Review, the New York Times, the Wall Street Journal, CIO Magazine, and Brand Quarterly Leader to Leader. She has an AB from Harvard College and an MBA from the Stanford Graduate School of Business. To learn more or get in touch with Baxter, visit