Landing My Dream Job

I never thought I’d be writing this. I’m normally fairly private about my personal life and I prefer to let my actions speak for themselves but I realize things don’t “just happen,” there’s a journey and it’s important that we tell our stories in hopes that our story helps someone else.

A couple of months ago I landed my dream job on Scott Hanselman’s team. Now that I’ve been there for a month-and-a-half, I wanted to reflect on my journey. My whole professional and pre-professional career has always been centered around the Microsoft technology stack. I preferred it over some of the other stacks as it let me focus on getting something done and not messing around with weird command lines or complicated tooling.

Ten years ago, the only jobs at Microsoft in New York City, where I live, were field sales and consulting. I was able to get a job as a Technical Solution Professional (tech pre-sales), responsible for selling Visual Studio and TFS to enterprise customers in New York. I had never been in a sales role, but I knew the product, I knew the technology, and was ready to learn. And learn I did.

I learned how to give technical presentations, how to talk to customers and solicit constructive feedback, and how a sales organization worked. I learned a lot about myself as well. I learned that I love teaching people how to use technology to solve their problems. I also learned that I wasn’t very good at the networking aspect of sales, “breaking in” to an organization to find the decision-makers.

As I got to the end of my first year in sales, it quickly became apparent that my time there was up. In the “bad old days” of Microsoft, stack ranking was king and I was going to be compared unfavorably with my peers. I was also blocked by my manager from finding an engineering role within the company, even possibly moving to Redmond. I was told I “was not a fit for Microsoft,” and that hurt. A lot. I was being forced out of the mothership and rejected by a company I admired.

Not one to be caught unprepared, I reached out to some contacts and found a new role as a consultant at a small, young, firm — BlueMetal. I was the fourth person in the NY office, with only about 25 people there in total. Consulting was a natural fit for me. I enjoyed the variety offered by working on different projects, for different clients, helping envision and develop solutions to meet their needs. It was at BlueMetal that I was able to refine my customer-focused skills and start contributing to the .NET open source community. I started to become more active by speaking to a variety of groups. I began speaking at local groups, like New York Code camp, and was eventually selected to speak at Xamarin Evolve in 2016 — my first major conference as a speaker. I was driven to build my personal brand by helping others succeed, be it blogging solutions to difficult problems, creating tools to fill gaps, or answering questions and participating in the conversation on Twitter.

Along the way, Microsoft recognized my contributions in the open source space with an MVP award in Windows Development in 2014, and in Developer Technologies in 2016. In 2018 I was nominated and accepted as a Regional Director, a small group of recognized technical and community leaders who help provide insight back to Microsoft.

Having carved out a role as Chief Architect of DevOps and Modern Software, I was having fun but I wanted more. I wanted to have a bigger impact, to help more people and to be more directly involved in the technology stack that I spent my career around, so I reached out to my contacts in the .NET team.

They say, “good things come to those who wait,” and that proved true for me. Sure, it took longer than I expected but an opening on the .NET community team that focused on the .NET Foundation materialized and I jumped at the opportunity. I’d worked on the advisory council and then the board of the Foundation for the past few years. I’d worked closely with two prior Executive Directors during the organization’s transition from a closely held, separate organization into one with a publicly elected board with broad ambitions.

Even though I had experience and relationships because of my role within the community, interviewing with Microsoft and waiting for their decision was an anxiety-inducing experience. I work hard to exceed expectations, prove my worth and never take anything for granted. When the good news came, I was overjoyed.

In several weeks I’ll fly out to Redmond for the MVP summit. It’ll be my sixth one, though my first being on the other side of the table. I’m both nervous and excited, as the summit is the one time of year when I get to see many of my friends in person. I hope to share what I’ve been working on, my vision for getting the community more involved with the Foundation, for improving diversity and inclusivity in our ecosystem, and for helping show a new generation how C# and .NET can help them do more.