Why I joined Microsoft

Ashley Willis (McNamara)
Published in
7 min readJun 29, 2017


The best career advice I’ve received so far is, “Never turn down an interview.” I generally follow this advice because you only have so much time in life to make an impact. Recently, I realized taking your own advice is much harder than I imagined… which is how I *almost* turned down one of the biggest opportunities of my career.

What you’re about to read are first world problems.

Before I started working at Pivotal, I had the opportunity to interview with some amazing companies, one of which was Microsoft. I interviewed for two roles at Microsoft, both were DevEx roles, but for different business units; I turned down both roles.

You see… I love what I do. I love developer advocacy, but most companies don’t know what that means.

If your Developer Advocate rolls up under marketing, you’re doing it wrong.

If your Developer Advocate doesn’t have a direct line to product managers and the ability to suggest changes based on developer/customer feedback, you’re doing it wrong.

If your Developer Advocate is being used as a sales resource, you’re doing it wrong. (That’s called Sales Engineering).

The job of a Developer Advocate isn’t a one-to-one job, it’s a one-to-many job. As a Developer Advocate, you’re spreading awareness and enabling developers to do what they love; write, code, and learn. I turned down the jobs at Microsoft because they were NOT Developer Advocacy jobs and Microsoft doesn’t care about Open Source developers anyways… right?

Fast forward: I accept an amazing job at Pivotal on an awesome team with the best boss ever. I was having a blast, though I was getting daily emails from Microsoft recruiters, I was ignoring them because I had no intentions on leaving Pivotal.

So, there I was, working from home and minding my own damn business when I get a Twitter DM from Bryan Liston inviting me to ChefConf, which was being held in my hometown. See, both Bryan and his boss Jeff Sandquist had been taking turns trying to get me to entertain yet another role at Microsoft, but I’d already interviewed and knew that Microsoft didn’t know how to do Developer Advocacy. I continued to decline the role, but at the end of the day, I won’t let where someone works come between me and beers. I went to ChefConf and spent the day hanging out with Bryan, who did his best to convince me that this team was different, but I knew it wasn’t so I continued to decline.

Later on that day Bryan had booth duty, so I went and had lunch with a friend. I explained the opportunity at Microsoft and explained that I felt guilty for even talking about it, I had only been at Pivotal for 10 weeks. What kind of person leaves after 10 weeks? My friend said something to me, something that I’ll never forget, “There is no loyalty in business, Ashley. You’re a single mom. You have a family and you owe it to them to see this Microsoft interview through.” Some of you are probably thinking, “That’s just common sense, Ashley.” I know, but sometimes the feelings of disappointing your community or co-workers outweighs the obvious and I was so worried about disappointing Pivotal I was sick over it. Like, literally sick.

So, I sucked it up and told Bryan I would move forward with the interview process and within a week I was in Redmond. I’ll be honest — I was not at all excited about working at Microsoft. I’m an Open Source nerd, why would they even want me? Hell, I don’t even have a Windows machine… oh no, they’re not going to make me use a windows machine, are they?

I show up at 9am for my first scheduled interview with Jeff Sandquist. I’ve admired Jeff for a long time–Jeff ran Developer Relations at Microsoft from 2005–2013 (back when Microsoft did Developer Advocacy well) before leaving and joining Twitter as their Global Director of Developer & Platform Relations. Now he’s back as the General Manager in Microsoft’s Cloud and Enterprise Group, and he’s very focused on rebuilding Developer Advocacy at Microsoft. He’s even created a new team that rolls up under engineering, and that’s the team he wanted me to join. Jeff and I spoke for an hour about his plans and what he thinks success looks like and I realized that I was wrong about Microsoft, but not without reason. Back in the days of Bill Gates and early Steve Ballmer, Open Source was a dirty word. In fact, Ballmer compared Linux and the GNU General Public License to a “cancer”, a stance he later went back on, but at the time Microsoft felt Open Source to be a major threat. And to some extent, Microsoft is still fighting off the lingering perception they’re not big fans of Open Source.

By now it’s 11am and I’m off to my second interview, I’m feeling better about the role, but I’m still not convinced. My second interview was with Rimma Nehme, Architect on Azure Cosmos DB and Open Source Analytics. I was most excited about this interview because Rimma is a woman in a highly technical role and I was curious about her experiences at Microsoft. Rimma and I sat and chatted about everything from kids to women in tech, then I asked her what she’d been working on lately. Her eyes widened and she told me about Cosmos DB. She spent the next 30 minutes whiteboarding as I sat there with my jaw on the floor–for those of you who don’t know what Cosmos DB is, it’s the first globally distributed, multi-model database service for building planet scale apps. Designed as a globally distributed database system, Cosmos DB automatically replicates all of your data to any number of regions of your choice, and it supports transparent multi-homing and guarantees 99.99% high availability. Sounds like magic, right? I left that interview inspired. Cool things were happening at Microsoft, this was a new Microsoft and I wanted to be a part of it, but first I wanted to do some research.

Was Microsoft really a new Microsoft? Here’s what I learned…

It turns out that Microsoft has the largest number of the top 500 Open Source projects for any one entity. Microsoft has 24 projects, way ahead of Google and Pivotal (each having seven) and Red Hat, which has six.

Not to mention their own open source projects like .Net Core, Visual Studio Code and TypeScript, Microsoft is getting a ton of help from the open source community. Over 60 percent of the contributions in CoreFX .Net core libraries and CoreCLR .Net core runtimes are coming from outside Microsoft, and they’re contributing significantly to external outside Open Source projects, such as Linux, Docker, and Kubernetes.

Open Source is all about community and ecosystem. No company can survive without a healthy ecosystem and Microsoft knows it very well, which is another reason they’re investing in Developer Advocacy again.

Microsoft has over 15,000 contributors on GitHub and over 6,000 employees contribute to Open Source projects, and have released over 3,000 Open Source projects. Microsoft’s Open Source programs office tracks nearly 10,000 Open Source components, everything from NPM packages to Linux distros used by Microsoft teams.

Yes, Microsoft is using Linux in it’s own infrastructure. The company also recently moved Windows development to Git.

The culture within Microsoft is changing as we speak. Linux expertise is spreading across the company and Open Source is no longer a dirty word at Microsoft.

With the interviews from that day and all the new knowledge I’d gained from doing my own research, I was now convinced that Microsoft was changing for the better, but was it enough to get me to leave Pivotal just 12 weeks after joining?

I made a list of pros and cons, Microsoft won hands down. The impact I can have at a company like Microsoft could be huge and at the end of the day, that’s what it’s about, right? All that was left was the question of Windows or Mac. I’m happy to report that Microsoft does, in fact, give their employees Macs. See? A new Microsoft.

I feel like I just did a lot of rambling with stats and whatnot and you’re probably thinking, “That’s all good and great, but really, I just want to know what happened at Pivotal? Who wronged you?” The answer is nothing and no one. Pivotal is a great place to work and I feel so fortunate to have been there, even if just for a short time. I’ll miss my team terribly and anyone reading this would be lucky to call Pivotal their 9–5 home.

That being said, I’m excited about starting my new chapter at Microsoft as a Principal Developer Advocate and as a bonus I’ll continue working with my Pivotal friends because Pivotal just announced a partnership with Microsoft!

So, two lessons here:

1) Never turn down an interview.

2) Companies CAN change.

[MSFT has made huge strides, but there’s still so much more that needs to be done]

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