throwaway_23124

> I'm a little confused on how you are interpreting the majority of your customers opting for discounted pricing as an indication that you should raise prices.

The way I see it, most customers are happy enough after a 30-day trial to commit to my product for at least a full year. That's a good signal for loyalty and the product being worth it for the price. While I agree that the discount aspect is a signal in the other direction, I think overall it looks like people will continue to subscribe even if it's pricier. That's why I'm leaning towards increasing prices. I don't know much about businessy things and I'm learning as I go, so take my opinions with a grain of salt.

I've had some really good suggestions in this thread to talk to my most recent subscribers to really understand why they paid annually straight off the bat, so I'm going to do that first before taking any action.

I see. My product is somewhat in between B2B and B2C (i.e. plenty of regular folks subscribing for their personal use, but also plenty of companies using it). Perhaps this is a strong signal in favor of price segmentation to make future B2B customers more than personal users?

I absolutely don't plan to change any existing subscription; everybody always gets grandfathered in forever. The early adopters' invaluable feedback + potential bad rep from raising prices is reason enough. I'm mostly looking for advice on how to price things for my future customers :)

>2 months off for paying annual pricing is a very good deal for someone who plans to use you product on the long term.

I too pay for some things on an annual basis (e.g. email). I guess never expected my product to be sticky enough for people to want to go annual straightaway. To be very blunt because I'm anonymous, how do I monetize this stickiness to extract maximum value from future customers?

>On the yearly subscription, do you charge for the entire year upfront?

Yes. The annual subscription is < $250/year, so I don't believe it's expensive enough to stop people purely because it's a big charge.

>How is the distribution of vintages of your user base?

My startup is fairly new (12-18 months old), so I don't have much insight into such statistics. However, I will note that growth has somewhat stagnated (<4% MRR growth every month). While I'm not looking to grow rapidly and I don't have any external pressure to grow (no VCs :)), perhaps the stagnation is a good motivation to introduce segmentation, higher prices, etc.

>it’s almost always a good idea to do it without disrupting (too much) your existing user base.

Absolutely. I always grandfather existing users and I have a few dozen very early users who are paying peanuts compared to the current pricing. I value their super early feedback a lot in shaping my startup, so I'm happy to grandfather their subscriptions forever. I even get emails every now and then from some early users asking if I could "upgrade" them to the current, higher pricing!