What 2 Years at Microsoft can do (with the right team)

09 Feb 2024 12:11 UTC-05:00

It's amazing what you can learn in less than two years.

When I joined Microsoft I had one mission, help the Python community and few people like me in it. It was that simple. I was leaving my first DevRel gig and an amazing team of folks that I still try to keep up with to this day (Although it seems they've mostly headed to other places as well). The team I was joining was made up of two people I had looked up to for the majority of my time as a Python developer.

Jay with Nina and Ant - My Python Team when I started at Microsoft

I would also be across the virtual hallway from folks that were mentors in my tech career that would be inspirations to me to this very day.

Python Team at EuroPython

I was there for perhaps Microsoft's greatest shift of focus, moving into the AI space. I would see the push and pull that it would bring to developers and companies alike.

My first year was about learning how to think like a Microsoft employee. I would learn about thinking at scale and planning BIG. If you weren't making potential moves that could save hours of time or bring multiples of your salary in revenue, then it needed to better align with OKRs. I learned to fill a lane and play a role on a bigger stage. I would also learn that careers are personal and decisions in them are as well. I would lose two of my potential mentors before I would even start at the company and one more before making it 6 months in.

Jay and Ashely Willis

You don't go to Microsoft to make a new impact (I'm sure that my mentors will roll their eyes at me saying this). Microsoft is like the New York Yankees in the late 90's/Early 2000's. They were likely going to the World Series (I mean 6 out of 8 years between '96 and '03). If you became a Yankee, your job was to play your part and work hard so that when Jeter raises that trophy you can say you were there. You can flash the ring and then you get ready for next season when you do the same thing. You aren't the star. Shave your face and do your job.

Jay at a Braves Game because Like Hell you're catching at a Yankees Game

My first year I felt like I did that. I played the role and I still had some big hits. Like giving my first keynote with Melanie Arbor!

Jay and Melanie on stage

Photo by Bartek Pawlik - bartpawlik.format.com

My second year was the one where I wanted to be louder. AI was here to stay. The description of my job (and technically even my job title) had changed. In many ways I did what I could to hold onto my mission.

Luciana Rocking the Booth I was responsible for coming up with a lineup for

I also worked between the lines to empower communities and even launch Black Python Devs, the most important thing I've done in my time as a Python Developer. My team at Microsoft was extremely helpful in making this happen and so were many of my mentors that I made during that time.

Black Python Devs at DjangoConUS 2023

Photo by Bartek Pawlik - bartpawlik.format.com

In a bittersweet reality I have learned for myself that careers are personal and decisions in them are as well. Today ends my time with Microsoft. I'm off to push myself in a new direction with more responsibility and challenges. I'm happy that I was a member of Microsoft in this pivotal moment in their evolving story. I'm also happy that more than anything that Microsoft did for me was give me confidence as someone in the Python community that people look to for insight. They also gave me confidence in my ability to create content and represent a company and a community without feeling as if I sacrificed my place in either.

I want to give a special thanks to everyone on my team and the folks that I got to work with on a regular basis. You made our time together really special and I freaking cry at the thought of not getting to act silly with you.

I'll be sharing what's next soon but know that I'm not leaving DevRel and that I'm going to a place where I feel I can make an immediate impact and help them establish a strong relationship in the community. Be on the lookout for the next announcement but thank you to all the folks that helped me to get here and help me build the confidence that it takes to make a move like this.

Jay Starting Microsoft vs Jay a couple months before leaving