The man behind the brilliant satire at ClickHole is headed to Seattle to answer a quintessential comedy question: Can you make a machine funny?

Jamie Brew, the Chicago-based website’s former head writer, will join the three-month Alexa Accelerator Program as one of the entrepreneurs and companies trying to improve Amazon’s Alexa smart speaker. Brew, along with Bob Mankoff, previously the cartoon editor of the New Yorker, founded the tech company Botnik, which has a predictive text feature that (they hope) can make Alexa funnier.

We caught up with Brew about his move, which was announced today.

You’re leaving Chicago! (Disclosure: This writer worked with Brew at Clickhole.) Are you going to miss your time here and at ClickHole?

Of course I’m going to miss ClickHole! That group of writers and friends and just people—you are asking me to get sappy here—I’ve never loved working with a group of writers more. Chicago has been such a home to me in the past five years, from being a fellow at The Onion to being one of the founding few at ClickHole. The Chicago community of artists is just so invigorating to be around, and has been such a receptive audience. I will miss Chicago like crazy. It was the true incubator.

Tell me more about Botnik’s predictive text feature.

It is directly inspired by your phone’s predictive text, the feature at the top of your touchscreen keyboard that gives you three suggestions of words that are likely to come next in the sentence. While the phone feature predicts based on its general collection of texts and emails, this feature predicts based on whatever source text you want to plug in [i.e. a paragraph from a book] and it offers many more options. Instead of the computer trying to guess what you want to type, this new interface is trying to surprise you and offer new options that you didn’t have in mind. It’s not trying to guess your intention, it’s more creative.

Where did you come up with the idea?

The suggested words on your phone are like a garbled and boring business email. It takes away all the creative elements of the computer itself. Both the user and the machine bring something to the table. With this feature I have developed, it expands the options to nine or 15 words that are plausible next steps in the sentence.

You’ve personally used this tool for songwriting and scripts. Does it make the writing better or worse?

It’s just a different kind of writing. The point is not to speed up the writing I would do anyway; the point is to do something different, that the computer and I would not do on our own. It’s a collaboration between yourself and the machine. It’s cyborg writing. It’s very different from my normal writing and maybe it has even affected my normal writing.

Now when you write without it, do you ever wish you had it?

The funny thing about the machine is that it takes the same first steps as you would as a writer, such as figuring out what phrases make sense for the chosen genre. With certain kinds of comedy writing, you want to evoke a writing style or a particular writer.

So how do you think your program could be incorporated into Alexa?

Well, the way Alexa is set up is she has a bunch of skills, each developed by different people. Our hope is to give the computer a sense of play: It doesn’t always have to be practical and geared for just information.

But humor is a very human and personal trait.

We aren’t trying to make the computer tells better jokes. We want to make the interaction between a human and the machine fun, and that’s not a matter of making the computer funnier, but making the way it talks fun or more interesting or more collaborative. We aren’t trying to outdo comedians at their jobs and we aren’t making the jokes.

What happens after the three-month program?

This summer is time for us to develop the application more and see how it works with Alexa. We present our product to a room full of potential investors in October called Demo Day. It’ll be great and I am excited to start.