Design

Retention Through Useful Features

Dec 09, 2015

I recently introduced a major new feature in Cushion—weekly summaries. On the surface, this might seem like a feature that originated like others. Maybe a user suggested it or I desperately needed it myself. Surprisingly, this wasn’t the case. Weekly summaries is the first Cushion feature that came from a behavioral need—user retention.


Cushion is nearing its 2nd birthday and appears to be doing well. I’m not ditching client work just yet or doing snow angels in money, but it’s on a consistently upwards path. Cushion should be growing faster, but something is holding it back. For every handful of new subscribers, a paying customer cancels. That “churn” word, that everyone in the SaaS world talks about, becomes the latest addition to my vocabulary.

Through conversations with users who cancel, I started to notice two patterns—1) most users don’t use Cushion on a regular basis, and 2) most people cancel their Cushion account because they don’t use it enough. When you think about these two patterns in parallel, it’s easy to see that they are directly connected.

The original intention of Cushion, however, was to fit this exact use-case. Because it visualizes a bird’s-eye view of your schedule and income, you don’t necessarily need to check it as much as you would a time-tracker or to-do app. To me, that’s a benefit—allowing users more time to spend on their actual work. Unfortunately, this doesn’t help with retaining paying customers. As people use Cushion less, they no longer equate the value with the monthly cost. Slowly, the cost of this week-to-week tool doesn’t feel as justified as an everyday app.

By designing Cushion so users don’t need to use it every day or every week, I have essentially built a churn machine. There’s nothing to pull users back in—they need to remember to come back. As a result, I need to straighten the ship and focus on user retention.


The most common way to bring users back is through email. Unfortunately, many apps abuse this approach by using marketing techniques that don’t have the user’s best interest in mind. As a user of many apps myself, I refuse to follow the playbook of assaulting email inboxes with opt-out drip marketing or other spam-like techniques. If I knew upfront that signing up for a service signed me up for a dozen unwanted emails over the next two weeks, I wouldn’t sign up. That should be an opt-in preference upon signing up, for users who need guidance.

retention-weekly-summary

Instead of using a marketing technique, I decided to improve retention with a new feature—weekly summaries. This way, users get a reminder to log into Cushion, but they also receive personalized insights that are useful to them—not a blind tutorial for a feature they might already know how to use. By providing users with data that’s actually useful, Cushion is starting out the relationship by being respectful rather than texting them every day and hoping they text back.

As an avid Slack user, I always look forward to their weekly summary email for the rooms I own. Most of the information is intended more for the project manager type, but I find it interesting nonetheless. I imagined what this email would look like for Cushion—what would be useful for freelancers to see after each week.

retention-graph

The most obvious insight is income activity. In Cushion, this means the amount you were paid that week, the amount you invoiced that week, and a sum of late invoices. All three of these are useful because they have the ability to either boost your spirits or kick you into gear. If you had a few paydays, you can pat yourself on the back. If you didn’t see a dime that week, this could serve as encouragement to either track down late payments or take on more work.

retention-outstanding-invoices

If a user has any late income, they would probably want to know which invoices are late. Under the graph, Cushion lists all of the outstanding invoices for that week. The list includes the relative due date of the invoice along with its amount. Instead of showing a MM/DD/YYYY-formatted date and forcing the user to calculate when the invoice is due in relation to the current date, Cushion will show “tomorrow” or “3 days ago”—much easier to process at a glance.

retention-active-projects

Then, below the outstanding invoices, Cushion lists the user’s currently active projects. Each one includes its relative start date and the estimated time remaining on the project. This gives the user a sense of how long it’s been and how far is left to go. If there are any listed projects that are no longer active, users can easily click the project to open Cushion and update the project’s status.


The email doesn’t seem like much, but it does a great job of keeping users informed on a recurring basis while reminding them to check in from time to time. Instead of blasting everyone with the same static email, users receive relevant data that they opted-in to receive.

I consider this Cushion’s first step towards establishing a routine for users. Every Monday morning, they can expect to receive their summary, and knowing this will prompt them to keep their account up-to-date. So far, it’s a great success. A handful of users have already let me know that they use Cushion more because of it—they feel the need to ensure everything is accurate before their weekly summary arrives. Considering my goal with this feature, that’s like music to my ears.

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Archive

  1. Funding Cushion
    Story
  2. Hiring a Team of Freelancers
    Story
  3. Taking a Real Break From Work
    Story
  4. Slack as a Notification Center
    Dev
  5. Document Your Features
    Story
  6. 300
    Story
  7. Vacations
    Design
  8. Offering Discounts
    Design
  9. Waves of Traffic
    Story
  10. Less Blogging, More Journaling
    Story
  11. Retention Through Useful Features
    Design
  12. The Onboarding Checklist
    Design
  13. Spreading the Word
    Story
  14. From Beta to Launch - The Subdomain
    Dev
  15. From Beta to Launch - Sign up
    Design
  16. From Beta to Launch - Messaging
    Design
  17. Launch
    Story
  18. Authenticating with 3rd Party Services
    Dev
  19. Intro to Integrations
    Design
  20. Inspiration vs Imitation
    Story
  21. The Emotional Rollercoaster
    Story
  22. Designing Project Blocks
    Design
  23. Everything in Increments
    Story
  24. Deleting Your Account
    Design
  25. Designing the Subscription Page
    Design
  26. Rewriting the Timeline
    Dev
  27. Restructuring the Individual Project Page
    Design
  28. Project Blocks
    Story
  29. Redesigning the Homepage
    Design
  30. Multiple Timelines
    Design
  31. Archiving and Estimate Differences
    Design
  32. Multiple Financial Goals
    Design
  33. Zooming in on the Timeline
    Design
  34. Currency
    Dev
  35. Preferences, Accounts, and a Typeface Change
    Design
  36. Sending Out the First Email
    Story
  37. Currency Inputs, Notifications, and Invoice Nets
    Design
  38. Dots and Lines
    Design
  39. Calculating in the Database and Revealing Tendencies
    Dev
  40. Improved Form UX
    Design
  41. Cushion is Online
    Story
  42. Schedule Timeline Patterns
    Design
  43. A Slimmer Schedule Timeline
    Design
  44. The Schedule Timeline
    Design
  45. Plugging in Real Data for the First Time
    Design
  46. Transitions and Project Lists
    Design
  47. Death to Modals
    Design
  48. The Individual Project Page
    Design
  49. Estimated Incomes and Talks with Other Freelancers
    Story
  50. Statuses to Lists and the Paid Beta
    Story
  51. The Timeline
    Story
  52. Invoice Terminology
    Dev
  53. Modal Forms
    Dev
  54. Wiring the Backend to the Frontend
    Dev
  55. Balancing Design and Dev
    Story
  56. Timecop, Monocle, and Vagrant
    Dev
  57. Going with Ruby and Sinatra
    Dev
  58. Ditching local-first and trying out Node.js
    Dev
  59. Switching to AngularJS
    Dev
  60. Building the Table with Vue.js
    Dev
  61. Clients, Projects, and Invoices
    Dev
  62. Introduction
    Story

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