How to Upgrade Your Early Adopters (and make them happy to pay)
This morning, I received the email below from Alex at Baydin. They make a fantastic Gmail extension called Boomerang. Of all the upgrade emails I've received over the years, this one stands out because it does the following:

(1) Expresses gratitude

(2) Provides context (my early donation; the year of free service they gave me)

(3) Presents me with clear options

(4) Offers a sweetener

(5) Has a clear sign up option

(6) Recaps product developments

(7) Offers me a simple unsubscribe option

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Dear Boomerang VIPs -

First, let me say thank you.

You voluntarily signed up for a paid subscription to Boomerang, before we had any pricing plans in place. Because so many of you chose to pay for the service early, we were able to demonstrate to potential investors that our service was providing a lot of value. That gave us the ability to raise the funding that allowed us to continue developing Boomerang over the last year. Without you, we couldn’t have done it.

When you bought your subscription, we asked you to pay whatever amount you thought was fair for a one year subscription to Boomerang. When we converted Boomerang to a freemium service last July, we set you up with a one year Pro-level subscription.

I’m writing today to let you know that your subscription will be a year old next month. There are two ways you can continue to use Boomerang.

[1] You can renew your paid Boomerang subscription. If you choose to continue on the Pro service level, your service will maintain the same feature set that you have been using over the past year. If you choose the Personal service level, you will no longer have access to some premium features, but you will still be able to schedule unlimited messages.

[2] You can use the Free Boomerang Basic plan, which provides 10 scheduled messages per month and access to the basic features in Boomerang, as long as you’d like. If you do not choose to renew your paid subscription, you will automatically convert into the Boomerang Basic plan on July 15th, and all messages that you schedule before that date will be delivered as scheduled. You don't need to do anything if you want to use this plan.

Your early support was crucial for us, so we want to make sure we show our appreciation for your help. Please sign up using the link below, and we will apply a 40% lifetime discount to your account. Your Pro subscription will convert to a Basic subscription on July 15th, so to continue using Boomerang without interruption, please sign up before July 15th.

Sign Up Here [Link]

Over the past year, your subscriptions have enabled us to make dozens of improvements to the service:
-Boomerang Mobile released in September. It’s the only way to schedule an email from your smartphone.
-Boomerang added the ability to schedule recurring emails in November. Gmail with Boomerang is the only mail client with this feature.
-Boomerang now lets you add Notes to messages that you schedule to return to your Inbox. They make it easy to remember why you Boomeranged a message several months back.
-You can now Boomerang messages in bulk. Check up to 10 messages in your Inbox, and Boomerang will return them all at a later time.
-Finally, earlier this month, Boomerang added the ability to schedule a follow-up message, and have it only be sent if the recipient doesn’t respond to your original message.

Thank you again for becoming the first paying Boomerang customers. We’re glad we’ve had the opportunity to provide this service for you, and we look forward to continuing to work with you in the future.

-Alex and the Baydin Team

Unsubscribe from these emails [Link]