Alexa, show me the door

Jonathan Aisenberg
Open Ais
Published in
3 min readJul 14, 2017


A lot has happened since I wrote about leaving Microsoft in 2014. Since then I’ve worked at two start-ups, had two kids, and returned to Microsoft to find what I was missing the first time around — a meaningful role where I felt I was learning, growing, and making a difference. I returned to a great team solving an important set of problems, and really began to feel at home.

I distinctly remember the night I was to return from paternity leave how excited I was to return to work, and commenting to Katie that I finally felt I was in a place in my career where I could really grow for a while, where the sky was the limit.

Microsoft makes it easier to be a dad in more ways than one

Which is why I can’t believe I’m saying this again: but I’m leaving Microsoft…again.

The short version of the story: I returned from paternity leave to a massive re-org: a new division, a new manager (or, rather, the lack of a direct manager), and very little to do. This would be starting a new job, and not one I would have applied for. I was of the opinion that if I’m going to be starting a new job, it should be one of my choosing, so I began looking for a new role internally. But after three months of recruiting basically full time…I once again found a better role outside the company faster than I found one inside of it. I’ll admit to being weary of the intra-Microsoft job hunt, and was less willing to stick it out for as long as I did the first time in hope that something would materialize in Redmond.

But I’m super excited about the opportunity ahead: I’ll be working on Amazon’s Alexa Skills team to bring more capabilities to the Alexa platform. And I get another opportunity to work with a good friend and fellow Simply Measured veteran, Uri.

When I feel that pang in my heart about leaving again, I keep telling myself that companies aren’t sentient beings; they don’t have thoughts or feelings about you. It’s not that they don’t care about you, it’s that they’re incapable of caring about you; be careful about the feelings you develop for them because they’ll never return the affection. Do right by the people you work for and work with, but do what makes the most sense for you and your family. And for me that means a change in scenery from the East Side to South Lake Union.

You want to know what I really think about Microsoft? I think it’s a great place to work, with some of the smartest and some of the kindest people I’ve worked with. I’m going to miss them a lot. And I can’t tell you how grateful I was to receive the generous paternity leave that Microsoft offers, and what a difference that made for our family.

So I wish all my former Microsoft colleagues well, and hope our paths cross again someday down the road.

Alexa, start new adventure.