5 tactics that converted 30% monthly paid users of my tool to annual plans

Hello PH family, After multiple experiments (both failed and succeeded ones), I have developed a list of 5 practices that actually worked for us to convert monthly paying users of SocialBu to yearly plans: 1- Ask for the upgrade when user's happiness is at its peak User happiness is generally highest right after you have resolved their issue/query in time. This is definitely the best time to ask for an upgrade since the customer is already happy with your service. You can simply send them an email or in-app message asking if they'd be interested in switching to an annual plan, and offer a discount if they do. 2- Offer yearly upgrade instead of custom plan Ask user to upgrade to a yearly plan instead of a custom plan if they want a little add-on or just want to increase their feature limit by a small margin. 3- Offer discount to product promoters If you use a Net Promoter Score (NPS) system, you can offer a discount to those customers who score your product or service as a 9 or 10. This is because they're already promoting your business to others, so they're more likely to be interested in an annual plan since it would save them money in the long run. 4- Keep enabled yearly pricing on pricing page If you have a pricing page on your website, make sure to keep the yearly pricing option enabled. This way, customers can see that it's an option and may be more likely to choose it instead of the monthly subscription. FOMO (fear of missing out) will make users feel as though they are missing out on something amazing if their price is changed from yearly to monthly. 5- Give a discount gift to loyal users Giving a gift is always a nice gesture, but it's especially appreciated when it's given to show appreciation for a long-term friendship. On user anniversaries - such as quarterversary, semi-anniversary, and anniversary - provide them with a discount on yearly subscriptions. Hope, it was helpful. Would love to know your experiences :)