Wrapping Up My Latest Microsoft Chapter

Three years and a quarter ago, my hiring manager asked me - “How do I know you’re not going to leave Microsoft again if we hire you?” It’s not an unfair question to ask, especially considering that I was going for my third stint at the company. My answer to that was pretty simple, at least from my vantage point - I can never guarantee this, but I will give it my all to build the best product imaginable because I live and breathe developer experience.

Three years and a quarter - that’s how long it took me to decide that it was time to close this chapter of my Microsoft adventure. Today is my last day at the company, and next week I’ll be diving headfirst into a new challenge.

Developer Division & CoreAI

It’s more than a bit of a bittersweet moment, because the team and the role I was in were fantastic. After being there for the past year (the previous two I spent working in Microsoft Security), I can tell you that Developer Division, or DevDiv as folks called it before it got folded into CoreAI, is an extremely fun place to work. I’m not just saying this to be nice - it really is the place to be at Microsoft to ship fast, learn fast, and be on the cutting edge of what developers use every day.

This was my dream org since I joined Microsoft. We’re talking about the birthplace of Visual Studio, Visual Studio Code, C# (and the .NET platform), TypeScript, Visual Basic (that’s what I started with way, way back), and so much more. Could an absolute engineering geek ask for a better place to be?

It’s something I always aspired to be a part of, and through a mix of luck and a whole lot of very much unrelated and very much unexpected stress, this dream became reality in the very first weeks of 2025.

Since January of last year I had the privilege of tackling many interesting problems, like helping figure out the adoption blockers for GitHub Copilot, charting out the path for better authentication and authorization integration in our IDEs (I guess I put my Entra ID knowledge to use here too), building quite a few conference prototypes and demos, training the internal Model Context Protocol (MCP) security muscle, and most recently - launching GitHub Spec Kit, which blasted past 61,000 stars on GitHub. Like I said, this org is lots of fun, and I had a lot of agency to do things that are impactful.

Oh yeah, and did I mention that GitHub Spec Kit is the second most starred repository in the entire GitHub org? Talk about a little experiment getting out of hand.

But as with any career step, sometimes the chutes and ladders drop us in wildly unexpected directions. That’s exactly what happened here. The timing is a bit odd, considering that just this fall I shifted roles, but I knew deep down that the change was something I had to do - at least to try and apply my skills at a different scale. I’ve done moves like this in the past, but this one feels particularly poignant - and yet, very exciting.

Acknowledgements

I wanted to take a moment in this somewhat long-winded blog post to express my immense gratitude to a few folks who were absolutely instrumental to my career in the past few years and even way before then.

It would be a grave disservice to not first call out just how impactful the work of Amanda Silver is on everything that I did at Microsoft and even outside of it before coming to DevDiv. People might not know just how big of an influence she is on cultural, technical, and product direction in Microsoft’s developer ecosystem - she truly is second to none when it comes to understanding developers. In my eyes, Amanda is the Developer Division. I owe her my position in DevDiv and CoreAI as a whole - she did the most for me of any managers or mentors in the past half decade, and I know a lot of folks who feel the same way. My biggest reservation about leaving Microsoft was that I won’t get to work with Amanda on the same team.

A few other folks that I want to individually call out for all they did to help shape my latest Microsoft tour of duty:

• Simon Calvert, who provided a whole new perspective on what product leadership really stands for.
• John Lam, because GitHub Spec Kit would not happen without his work and research. When I think of someone who thinks outside the box, John is at the top of that list.
• Jeff Wilcox, who is always a voice of reason I can count on in the most uncertain moments.
• Clint Rutkas, who brought me to Microsoft and continued to be one of my best friends and trusted advisors for more than a decade now.
• James Montemagno, a ray of positivity and optimism who is best known for his “Let’s do it!” attitude.
• Scott Hanselman, who needs no introduction. His advice has guided me since his early podcast episodes and through my Microsoft career.
• Scott Hunter, who didn’t shy away from sticking his neck out for me in some of the toughest situations.
• Brian Peek, who provided a good dose of realism almost every day.
• Brady Gaster, who provided friendly support and lots of product suggestions that steered my projects in way better directions.
• Caitie McCaffrey, arguably the most impactful internal MCP champion who knows about distributed systems more than anyone I know.
• Henrik Metzger, the fearless leader of the Microsoft Identity Service Essentials (MISE) engineering org, who helped me build a much better understanding of the security world.
• Jenny Ferries, who was never afraid to say the right thing, and most importantly, do the right thing.
• Jackson Davis was my go-to conversation partner in the past year, and I think he secretly is the most interesting man in the world.
• Jean-Marc Prieur, the only person I know who knows more about identity than the entire security org.

Also, very special shout-out goes also to some of the most amazing folks that I had the privilege of crossing paths with, who more than once helped me beyond what one could even ask for: Julia Kasper, Annaji Sharma Ganti, Tyler Leonhardt, Mandy Whaley, Scott McMurray (Halo Studios), Diviyan Matheendran (Halo Studios), Nancy Anderson, Jeff Carnahan (Halo Studios), Toby Padilla, Mike Kistler, Lutz Roeder, Josh Free, Peter Marcu, Peter Maytak, Gladwin Johnson, Neha Bharghava, Keegan Caruso, Josh Lozensky, Kelly Song, Bogdan Gavril, Ray Luo, Travis Walker, Adrian Frei, Iulian Cociug, Chris Mann, Christopher Scott, Saeed Akhter, Stephen Halter, Stephen Toub, David Fowler, Joe Binder, Paul Yuknewicz, Shayne Boyer, Maddie Montaquila, Pierce Boggan, Maria Naggaga, Ernie Booth, Cassie Breviu, Eric Hollenbery, Hemory Phifer, Matt Ellis, Matthew Reyermann, Martin Woodward, Mario Rodriguez, Chuck Lantz, Tim Heuer, Denizhan Yigitbas, Evan Boyle, and a massive fleet of other Microsofties and Hubbers who I learned from every day.

And of course, shout-out to the Microsoft-internal MCP Security Core Crew - the “deep into everything security” people I’ve been collaborating with in the past year to make sure that we improve the MCP security posture inside Microsoft and outside of it (I think we did a pretty solid job): Barry Dorrans, Alex Sklar, Matthew Henderson, Nazmus Sakib, Stuart Schaefer, Tolga Acar, Diana Smetters, Pam Dingle, and David Parks.

Onward

If there’s one thing I’ve learned in my career - the tech industry is a ridiculously small space. If we worked or otherwise collaborated together, I am sure that we’ll run into each other again many times in the future. Guaranteed.

Will share more on the next adventure soon!