Editor's note: This series is based on our new Alexa Skills course, How to Design for In-Skill Purchasing. This free course outlines the best practices for designing a great monetized Alexa skill experience.

Welcome to Part 2 of our series on designing skills with in-skill purchasing (ISP)! In Part 1, we discussed the different types of ISPs, and scoped a hypothetical trivia skill – Seattle Super Trivia – for three kinds of purchases (a subscription, some one-time purchases, and a consumable). Now that we’ve established some best practices for what to offer, it’s time to decide how we’ll offer these products to our customers. Specifically, when we’ll tell them about what they can buy. In Part 3, we’ll discuss how to write an effective upsell message, but we need to decide when those messages will appear first.

Unlike an app, skills don’t have a screen to use to remind a customer of purchases that are available: There’s no buy button in a skill, no modal windows, and no popups. A skill that offers in-skill purchases is most effective when it follows some of the best practices one might experience in a live sales conversation: The skill will need to engage the customer, get to know them, build trust and excitement, then ask for the sale at the right time and follow up in a way that isn’t intrusive or annoying.

No one likes a persistent car salesman that constantly tries to push their customers to buy a car that isn't right for them. Your skill should avoid pressuring your customer to buy something. Don't offer them the tricked-out 2020 armored sports car with all the upgrades before you find out the affordable, no-frills daily driver was the best fit for them: They'll have walked away from your lot (your skill) already.

Engage the Customer First

Customers receiving upsell messages during a conversation with Alexa only have the length of the upsell message and an open mic of eight seconds to understand what you’re offering and how it benefits their experience, then make a decision to say “yes” or “no.” That’s a heavy cognitive load for them to carry. A customer can’t make this decision without first becoming acquainted with your skill.

The best way to do this is to give the customer what they asked for first, wherever possible. If they asked your skill when the game is on, don’t make a customer sit through a subscription offer to listen to live games before answering their simple question (or worse, never answering at all). The customer should experience the benefit of your skill first. For example, the TuneIn Live skill will answer basic questions about your favorite sports team’s schedule before informing you you’ll need a subscription to listen. In our hypothetical trivia game – Seattle Super Trivia – this means we’re going to let the customer play their first game without mentioning in-skill purchases.

Here is an example of what NOT to do:

Offers Should Be Simple

Upsell messages ask the customer to process a lot of information, and we’ll want to reduce their cognitive load wherever we can. When a customer is confused, it’s just easier for them to say “no” to whatever is being asked of them. This means reducing the number of steps it takes to purchase and, for skills that offer more than one ISP, only offering one product at a time. For Seattle Super Trivia, that means we won’t try to sell the player a subscription, a one-time purchase, and hints at the same time.

Let's take look at an example of what NOT to do:

“Welcome to Seattle Super Trivia. It’s OK, you’ve probably never heard of it. Think you know Seattle? Think again, transplant. I’m about to school you! Before we get started, you can get a subscription to Seattle Super Trivia to get more trivia questions every day, purchase one of 50 mega-trivia packs, or stock up on hints before you do trivia battle. What would you like to do? Subscribe? Stock up on hints? Or get a pack?”

That was overwhelming. We threw a lot of information at the customer before they even got a chance to understand what the skill does. What are you likely to say to that prompt?

Complex:

Simple:

Be Relevant to Be Trusted

Offer an in-skill purchase when your customer will be most inclined to say “yes.” If you have multiple ISPs like our trivia skill, you’ll want to consider which to offer a customer first. For our trivia skill, we can offer a pack first since it’s an inexpensive, low-commitment purchase for those who’ve only played a couple times. If that customer returns to the skill and finishes our daily game of five questions several days in a row, that’s an indicator it’s a good time to offer them the subscription.

While the scope of your skill might affect when a customer is most likely to agree to a purchase, some milestones in their experience to consider surfacing upsells might include:

• A customer has run out of free content
• A customer has reached a point in the experience where it may be enhanced - but not blocked - by making a specific kind of purchase
• A customer has asked directly for content that requires payment
• When a customer returns to the skill for the first time since additional paid features were added
• When a customer has engaged with the skill successfully several times after declining the first upsell offer

Some inopportune times to surface an upsell might include:

• The first time the customer uses your skill
• The customer has asked the skill to stop, quit, or exit
• The customer has not recently had a positive interaction with the skill, such as after hitting several errors or not completing their primary task
• The customer has recently purchased from the skill and hasn’t used their purchase
• The customer has recently declined to purchase from the skill

Don’t Mislead, Confuse, or Disrupt

Don’t pull a “bait and switch” on your customers. They should clearly understand what kind of content they can access for free, and what content is “premium.” At the end of a round of Seattle Super Trivia, we’re not going ask our player if they want to play more trivia (of course they do!) and then tell them they can’t do that without a purchase:

Skill: Thanks for playing today’s round of Seattle Super Trivia. Want to play a another round?
Customer: Yes
Skill: Sorry, you’ll need a subscription to Seattle Super Trivia to play the daily bonus round. Would you like to learn how to subscribe?
Customer: No!

That was frustrating wasn't it?! Make sure you avoid doing this at all costs. Now let's take a moment to see what that would look like between two human conversational partners.

From now on, my poor player is going to be wondering when I’ll offer them landmines like that again, nervous every time they agree to an option that I’ll try to upsell them.

In the spirit of the discussion above about reducing friction and not trying to sell to someone we haven’t yet successfully interacted with (or haven’t even “met”), we don’t want to disrupt the experience they were expecting to get when they invoked our skill. In Seattle Super Trivia, we won’t stop customers with an upsell after agreeing to start their game. Let's make sure we AVOID the following:

“Ok, let’s continue your Seattle Superstars Trivia Pack. Before we get started, did you know we also offer 49 more trivia packs about history, animals, and music? Want to learn about more packs?”

Don't Upsell Too Often… or Too Little

When a customer declines to make a purchase, we’ll now have to decide when to offer a purchase again. Customers shouldn’t be shut out from purchases forever after their first “no,” but we’ll have to be contextual in the way we decide to make an offer again. Whatever upsell “trigger” we set, we’ll need to validate that mechanism. For example:

• If a skill offers a resource as a consumable that will be relatively scarce, a trigger to upsell when there is a low balance of such items is likely to deliver the message too often. Since Seattle Super Trivia only gives one hint a day for free, and offers a purchase of only three hints, we don’t want to set an upsell to trigger every time the customer only has one hint left: They’d be hearing upsells too often!
• If a skill upsell is set to be delivered every time the player is out of free content, they may hear the upsell as the welcome message every time they open the skill. Once a player finishes the Seattle Super Trivia daily game, we’ll want to offer the upsell again if they come back the same day, but if they decline that upsell, they shouldn’t hear that message over and over each time they open the skill until the next daily game is available.
• If a skill will surface an upsell after every trivia game the customer completes, the skill will deliver an annoying number of upsell messages if each trivia game is only three questions, while the skill may not deliver enough upsells if there are 100 questions per game.

Typical upsell intervals used by developers who have implemented ISPs include:

• Once every 24-72 hours
• After three consecutive days of play
• Once every set number of sessions

Consider a different, longer interval if a customer has already declined an upsell from your skill.

Now that we’ve decided what circumstances will trigger an upsell message and where, it’s time to write the message itself. But what do we write? How do we convince customers in just a breath’s worth of dialog? Stay tuned for Part 3 of this series, where we’ll discuss how to write an effective upsell!