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?

> how do I monetize this stickiness to extract maximum value from future customers?

Don't. Focus on acquiring more customers instead.

Or do it but without screwing current customers, use them as your free marketing force giving them even more discounts to honestly give you good reviews / recommend to their friends with a referral program. Instead of putting that money into adsense of fb ads, put into your current loyal customer base to help you grow it organically.

Worked for PayPal, Uber, AirBnB, etc..

> To be very blunt because I'm anonymous, how do I monetize this stickiness to extract maximum value from future customers?

Addons/extras/upsells. Find some features that might make the most sense as something that exists outside of your current pricing structure, maybe due to specific fixed costs of some sort that don't make sense to roll into the plan pricing, and offer them a la carte at like $20/mo or something. This would allow you to bump your ARPU a bit.

Another option is services. Not knowing your product, its hard to make any concrete suggestion here, but data migrations and initial account setups are common ones.

If your product is priced well putting a year down makes sense. I only want to worry about you once a year.

I've often thought about giving a one month option and a three month option (quarterly) and yet I haven't really seen this in SaaS... do you think there might be some people who would prefer to only worry about it once every three months?

It's the worst thing you could possibly offer.

Customers will notice a "large" bill every three months. It's just infrequent enough that they don't remember what it was from 3 months ago. It's just large enough that they really want to check where the hell is all that money going to. Customers will investigate and that can only result in cancellation.

A monthly subscription is designed to be easily approved by a middle manager (and fly under the radar). A yearly subscription is designed for customers who plan ahead or cannot do recurring payments (recurring invoices/approvals is a huge pain to deal with).

I found this really helpful, thank you!

A company I bought a plugin from, had a one fixed price for all time. They kept all the old customers in that bracked, but new customers have to buy a yearly fee.

So I would create a new subscriber role and simply let your new customers pay a bit more.

It is wise to be upfront with existing customers : say you have need for more funds or more investments, relay that to your existing customers, say you are keeping their price (indefinitely if possible) and that new customers going to go into the new tier.

He can keep that pricing tier/billing plan for existing customers and create a less generous one for new customers. I would keep reducing the discount until sales fall way off.

What metric confirms that correlation?

It's basic pricing strategy:

Kevin Hale - Startup Pricing 101

https://youtu.be/jwXlo9gy_k4?t=578

So if you drop the price a dollar the day before Christmas Eve, sales drop, you can't drop the price any lower?

you can grandfather existing customers into old plans and still experiment with pricing.