A Work in Progress


Best Year Ever

My first year at CloudHealth Technologies

Today marks my 1 year anniversary at CloudHealth Technologies . This last year has been a whirlwind to say the least. While today marks the anniversary of my start date at CloudHealth the story actually begins several months earlier.

In 2014 I was working at Springboard Retail who, I might add, are doing some awesome things in the retail space. On June 24, 2014 I got a message on Stack Overflow Careers from a guy named Joe Kinsella wondering if I might be interested in exploring opportunities at his startup. It was not your typical cookie-cutter recruiting email, his startup looked really interesting, right in my wheelhouse, and he just seemed like a guy i’d like to get to know.

I let Joe know that I wasn’t interested in exploring new opportunities, but that I would love to meet for coffee and talk about tech and what we were each doing. We met up for coffee at Flour Cafe in Boston and had a great discussion about our backgrounds, and our thoughts about the cloud and the future of the cloud. As Joe told me about his vision for CloudHealth I was immediately full of ideas and possibilities of what could be done. We had a great conversation and I walked away knowing that I would keep my eye on CloudHealth.

While I was very interested in CloudHealth I was still intent on staying where I was. I had been at Springboard for less than two years and I felt that I had an obligation to see things through a bit further (I was engineer #2, and the first engineering hire.)

Two days later I got an email from Joe introducing me to the CloudHealth CEO Dan Phillips. Dan was interested in meeting as well. I went to the CloudHealth offices and had a great conversation with Dan about the Boston startup community, and startups in general. That night I had a conversation with my wife and told her that I felt I should stay at Springboard a bit longer, but that I could definitely see myself at CloudHealth in the future.

Over the next month or so I was hard at work at Springboard doing really cool things like writing a cross-platform C library for interacting with POS hardware for the Springboard Windows, Mac, and iOS software. This was super fun but there was a thread running in the back of my brain that kept repeating “What do you want to do with your career?” I knew that retail was not my passion. My passions lie in scalability, distributed systems, the cloud, and building and understanding complex infrastructures.

Joe reached about to me again in August and asked if I wanted to catch up. A quote from my response:

Two of the thoughts that have been rather persistent at the back of my mind lately are “I don’t really want to be a Retail/POS expert. It isn’t my passion” and “I should check back in with Joe.”

The rest is history, as they say. I met the team, interviewed, was wowed by level of the engineering team and by just how deep the CloudHealth platform already was giving the company’s youth. Joe gave me an offer at Barlow’s restaurant on A St. I talked it over with my wife that night and we decided together that CloudHealth was the right place for me.

As an interesting aside: As this process was really kicking into gear I got a recruiting email about a “Core Engineering Team Position at CloudHealth.” I informed the recruiter that Joe and I were already talking. I found it very serendipitous and I couldn’t help but feel like CloudHealth and I were meant to be.

It was hard to leave Springboard Retail. They were really small at the time and I felt like I was abandoning them. I’ve been heartened to see how far they have come in the last year as well. I’ve kept in touch with most of the people there (though not as frequently as I would like) and I wish them all the success in the world.

I started a few weeks before AWS re:Invent 2014 and I was immediately thrown into the fire, just the way I wanted it. I merged my first Pull Request on my first day and its been that way ever since.

One of the most memorable parts of my first six weeks at CloudHealth allowed me to marry my love of building systems with my past experience writing C++ and building desktop applications. We hit an honest to goodness Chrome bug that was triggered by our charting library under some circumstances. In order to prove it I got to go all the way down to 2D drawing library in chrome where the error occurred. We logged a bug with the Chrome team and it ended up getting fixed in the next major version.

From there I have traveled around to various projects and features within the platform doing what I do best: shipping software! I’ve gotten into every part of the system. I’ve been given the opportunity to take on and solve big problems, learn new things from incredibly bright people, bring new engineers along, and take the helm building one of the coolest, most forward-thinking aspects of our platform.

It came full circle a few weeks ago in the ramp up to AWS re:Invent 2015 . We had the opportunity to build an integration with a new service ( AWS Config Rules ) prior to public announcement. I spent my last 10 days prior to re:Invent getting this built into the platform

I have been incredibly fortunate in my career. I had incredible mentors early on who guided me through a period of explosive career and technical growth. I remember those years very fondly and I’m grateful that I have had those people in my life. I was given the opportunity to take leadership positions as I matured, and to help bring others along. This is where I finally realized that the hardest problems in technology are the soft problems. The people problems. The greatest rewards also come from interactions with people (friends, family, co-workers, customers.)

With that all being said this past year has without a doubt been the best year of my career. The excitement of a startup that feels like its on a rocketship, the buzz, the velocity, the sweat, the intensity, the learning, the sleepless nights, the wins, the losses, the laughs, and the people. Most importantly the people.

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