A Look Back on Five Years


This December will mark my 5 year anniversary with Amazon. As I come upon this milestone, I thought it would be good to reflect back on where the last five years have taken me, how I’ve grown, and share some perspective.

We all have different experiences. I acknowledge that my experiences may not be reflective of everyone else’s. Even though there’s always room for improvement in terms of how things could have gone, I’m nonetheless thankful for everything and everyone that’s been a part of my life and career to this point–they have shaped me into who I’ve become.


Five years ago, I was living in San Antonio and working at USAA. It was a company that I had worked for since graduating from college in 2005. USAA was a great place to work for someone coming out of school, and it exposed me to a lot of areas of business and technology that would be helpful in the future. However, I was never really happy living in San Antonio. Prior to moving there, one of my friends in college (who was from San Antonio) referred to it as the “biggest small town” (which sums it up pretty well). It is a cute place to visit, maybe raise a family and retire. However, as a single young professional at the time, I found that the city did not have much to offer in a social scene that spoke to me.

My original plan at the time was to work there for 5 years and re-evaluate where I was at, see if I was going where I wanted, and make any changes necessary. Five years actually turned into eight years due to the economy and job market, and 2013 ended up being the year that I got serious about making a career change. At the time, I was working in IT Operations at USAA as a Sr. Unix Systems Administrator. My partner, Raphael, had given me the extra motivation to look for other opportunities to leave San Antonio.

Neither of us was happy in San Antonio. Raphael’s work was requiring a lot of travel and he was getting pressure to move to a location that was more centrally located since traveling from San Antonio almost always involved a connection. USAA had recently opened an IT office in Dallas and I approached my management about relocating (on my own dime) to Dallas so that Raphael could get some flexibility with his work (and we could both leave San Antonio). I was told by my manager that this wouldn’t be a possibility (despite at least one other person on my team who was allowed a similar remote work arrangement). They probably turned down my request to move since this was also the same time period where USAA announced they were going to shrink IT Operations through attrition. This ended up being a blessing in disguise since it prompted me to look outside the company for opportunities.

Even though I was willing to relocate at my own expense to take another position, I was having difficulty getting noticed with San Antonio listed as my current location on LinkedIn and resumes. I always knew that San Antonio was a limited market for IT talent, and this experience confirmed it. I still remember during one of the company-wide meetings, the CEO at the time said something to the effect that “if you don’t like it, you can quit and we’ll find 10 people waiting outside the gate to take your place.” That was the mindset there–that you should feel fortunate they continue to keep you employed. I can say that a number of my colleagues were good people who had happened to get comfortable with the work that they did. But I saw a few that were forced to look for other opportunities and were unprepared since their skills had stagnated over the years.

When I decided to leave USAA, I had made up my mind that I wanted to work for a company that was either a Cloud vendor or was heavily invested in Cloud. I saw what we were doing at USAA versus the rest of the industry and my fear was that if I stuck around longer, my skills would stagnate and I might end up like some of my other colleagues. I’ve always been a quick study when it comes to technology, so I set out on doing the best to market myself.

I had a lot of contact with recruiters (that’s a whole topic on its own) and some phone interviews. None of the positions were terribly exciting. I was almost starting to think that I’d have to just suck it up and take something decent, just to make the move out of San Antonio to a bigger IT market and use that as a springboard to something bigger. Just when I was getting ready to change my approach, a recruiter from Amazon approached me.

The Move to AWS

Around the October timeframe, a recruiter from Amazon approached me on LinkedIn for a Cloud Support Engineer position. I don’t remember what my thoughts were about the position at the time–I was actually more excited that it was a position with AWS. I had been following the work that AWS was doing in the Cloud (despite the fact that it wasn’t really on anyone’s radar at my employer at the time) and knew that it was kind of a big deal. I ended up going through two phone interviews (about a week apart from each other). Shortly after the second phone interview, I got invited to an on-site interview in Dallas.

I knew that AWS was in the process of forming a Dallas office, but I had no idea that I was about to get in on the ground floor. I remember I interviewed sometime in November, and I received a call from the recruiter about a week later with an offer! The thing that impressed me (and still continues to do so) is how fast Amazon moves. The offer was to start the first week of December. I had already had some vacation with USAA planned and was actually on my way to Puerto Rico when I had to put in my notice, in order to give the customary two weeks. Since I was on vacation, I actually had to phone in my notice (I felt really bad about this), but the alternative would have been to wait until I got back, which would actually mean less than two weeks notice.

Those two weeks were a whirlwind. I remember getting back from vacation and Puerto Rico and having to make a lot of arrangements. Thankfully, Amazon was very helpful in this area. The relocation package and experts they hooked me up with were amazing. I found out that my first three weeks with AWS were actually going to be spent in Seattle for training (since the Dallas office was so small at the time). In those two weeks, Amazon flew me to Dallas and paid for me to find an apartment. They also referred me to a local realtor in San Antonio (Kristi Maxwell, who was amazing!) and we got the house prepped and listed during this time. While I was in Seattle for my training, Raphael worked with the movers (which Amazon arranged to have them box and move everything) and they made the move to Dallas while I was in Seattle for three weeks.

Having three weeks in Seattle for training was an awesome experience. There is so much to the Amazon culture that you get by being in Seattle. The Dallas office was probably about 15ish people in size when I started–too small for us to do any training. I believe that my hire batch was like batch 4 or 5 and there were 5 of us. The Dallas office eventually grew to the point where we didn’t have to send people to Seattle for three weeks of training, which is kind of sad since I really got a lot out of that experience.

{% include image.html file=“amazon-handprint.jpg” description=“It’s a tradition in support for every new hire to leave their mark. This is my handprint on the wall in the Seattle office. Support in Seattle has since moved from that building, no word what happened to that wall.” %}

When I returned back to San Antonio from Seattle, I came home to an empty house just to pick up my car. Raphael and Bentley (our dog) were already in Dallas waiting for me. It was really strange seeing the house completely empty and making the drive to Dallas by myself that night. Those three weeks of training was some of the most intense learning that I had experienced. Starting any new job is stressful. I’m still very thankful for the support that Raphael and Amazon provided me in this transition.

It’s hard to believe that in the two weeks between job offer to starting with AWS in Seattle, I had to find an apartment in Dallas and sign a lease, interview realtors and list a house, and prepare the house for moving. I still don’t know how we did it. We were so busy at that time (Raphael and I) that I had to go to Dallas by myself to find the apartment. Thank you, Raphael, for trusting me on our apartment!

Life at AWS

This December will mark five years for me at AWS. I joined AWS as a Cloud Support Engineer back when our Dallas office was around 20-ish people. When I left USAA, one of my colleagues made a comment that “USAA must have really pissed Ronnie off for him to want to go do support work.” The AWS Cloud Support organization is much different than what you might picture a support organization to look like. I learned so much on that role–things that I never would have gotten the opportunity to learn had I stayed in my previous position.

The one difference that I tell everyone about working for a technology provider like AWS is that you get exposed to many different technologies and viewpoints. It is not a monoculture like if you were working for a company that just consumed IT. You get to see inside of other companies’ (your customers) operations and are exposed to their business challenges and their preferred approaches. You don’t get that kind of experience if you happen to just be working for one of these companies–they are mainly IT consumers. And as an employee there, you are most likely just working on whatever technology stack or direction your management has chosen and your ability to influence direction is likely limited.

As a naturally curious person, I thrive on getting exposed to new ideas and technologies. It makes me want to go learn the technology for myself. Looking back at my previous experience in a siloed IT shop, I know this would not have happened. As I write there, I think about all of the various items I want to highlight, but each one of them could be an article on its own. I’ll highlight a few here.

  • Interviewing: One thing that I’ve become very comfortable with is interviewing candidates. At the rate that AWS grows, it forces you to re-think hiring. One thing that is different is that everyone takes part in the hiring process at Amazon. As of right now, I’ve interviewed over 260 people for Amazon.
  • Software development: My college degree was actually in Computer Science. However, my roles after college were largely in IT Operations so I never got any experience developing software in an enterprise environment. At AWS, I actually got the opportunity to work on an internal tooling project and code functionality that was used by the entire worldwide AWS support organization.
  • Public speaking: I’ve come to realize the importance of being a good communicator. If you watch a number of IT presentations, you’ll find that while we may be smart, we aren’t the most dynamic people to speak on a subject. This motivated me to join Toastmasters and work to improve my presentation skills.

When people visit the AWS office in Dallas, they are surprised when I tell them about our humble beginnings. When I started, we were 20-something people in a Regus office. For those that don’t know, Regus is a company (think of them as being a more utilitarian version of WeWork) that rents individual office suites. We probably occupied six or eight suites at the Regus in Los Colinas (near the DFW airport). This was initially intended to be temporary in nature until we got our permanent space in Plano. However, due to items outside of our control, the Plano office plans went south and the company had to look for an alternate location. Eventually, we moved into some temporary space in the Dallas Galleria office towers while we waited on our build-out of the permanent space in the same building.

I’ve heard some people comment that Amazon operates like the world’s largest startup. We definitely had that startup mentality during those early months at the Regus, and later the floor 6 temp space in the Galleria. There was definitely some adjustment from the other tenants in the Galleria Towers when we moved in. IT engineers can definitely stand-out in their dress and personal appearance. On more than one occasion, I heard of comments from the other tenants to our engineers. Once, one of our engineers was coming back from lunch with a Jimmy John’s Sandwich bag, and one of the other office workers on the elevator said: “I didn’t know you guys deliver in the building.” I don’t think it really bothered any of us, but we saw it more as a reflection of the “old-school” attitudes of the other tenants at the time. Since then, it’s become obvious that we aren’t going anywhere and the comments have stopped.

My career has progressed pretty rapidly at AWS. After a little over a year in Cloud Support, I moved into a role as a Technical Account Manager on the Enterprise Support team. It was in this role that I got to work with some of our largest, most technically savvy customers. It was also in this role that I got promoted to the next job level. I’ve always tried to approach career planning and development with a long-term focus. The question I always ask myself is “is this position going to give me the opportunities and skills to where I want to be long-term?” This is what led me to my current role as a Solutions Architect. In this role, I’ve gained exposure to the sales side of the business, but it has also allowed me to leverage my technical skills. AWS (and Amazon) is really a very special place to work, and right now in my career, I can’t think of any other place I’d rather me.


Moving to Dallas and joining AWS provided a big change of environment for me. Not only do I feel like I’ve grown professionally, but I’ve grown personally as well. I’ve heard many people over the years talk about how the environment you’re in and the people that you surround yourself with makes a big difference in who you become, and to a lot of extents, it is true.

Raphael and I joke about “San Antonio Ronnie.” It’s largely a reflection on my mindset before I got serious about fitness. While I wasn’t overweight, my eating and exercise habits were definitely not trending in the right direction. It was in the Spring of 2014 that I decided to join a CrossFit gym, and CrossFit has been a big part of my life since then. I’ve gone on to do things like running two half-marathons, cycling and completing a 75-mile and 100-mile single day rides, and overall just eating better.

2014 was also the year that Raphael and I got married. We have been together since 2007, so this was a big milestone. I think that not only has society’s attitudes have changed, but I don’t have any fear at my workplace with AWS. While I won’t say that my previous employer was hostile towards LGBT, it definitely had more of a “don’t ask, don’t tell” kind of mindset for most of the time that I was there.

When we first moved to Dallas, our plan was to live in an apartment until we figured out what part of the city we liked, and then we would buy a house. When we moved to Dallas, we decided to rent an apartment in Uptown/West Village, which is very much an urban location full of townhouses, bars, restaurants, and shopping. This was a great experience for us since we never got to experience this in San Antonio (since it didn’t have an equivalent at the time). Work was still only a 20-minute commute north. After our lease was up there, we moved to another apartment in Victory Park (close to the American Airlines Center stadium), because Raphael wanted a downtown view. Yes, the view was good there, but we gave up being located close to walkable amenities. This is when we decided it was time to buy a house.

The nice thing about Dallas is that there are lots of cute neighborhoods and areas, each with their own distinct vibe. We had been living in Dallas for about 3 years up to this time and had become familiar with a lot of the areas. One thing was certain: We did not want to go live in the ‘burbs. We wanted to live within the city so that we could be close to all of the culture and amenities. We did get sticker shock when we started looking at houses (Dallas can be an expensive market, especially for a desirable neighborhood in the city), and we entertained a lot of different options. If Raphael could have had his way, we would have ended up buying a condo in Uptown (there’s no way we could have afforded anything outside of a multi-family style unit there). Thankfully, our realtor and I were able to talk Raphael out of the condo idea which meant we began to look at single-family houses.

After a lot of research, Raphael decided to focus our search on the East Dallas area. East Dallas is generally defined as the area east of the US-75 freeway and includes the area around White Rock Lake. A lot of the construction is 1930s-1970s and the area has a lot of charm. We wanted a house that felt like it had character, not your typical American cookie-cutter construction. We got very lucky and found a 1955 mid-century modern house that had been well taken care of and completely remodeled in 2008. We fell in love with it immediately. This house almost didn’t happen–originally the owners had received an all-cash offer and decided to go with that first. After a few days, I guess the original buyers backed-out so they ended up accepting our original offer.

Even though the house was in good condition, like the other house that we bought in San Antonio, we went to work making it feel like our home. I remember looking forward to two things as soon as we purchased the house: Buying a Big Green Egg and retrofitting home automation into the house. We love our neighborhood too! We got very fortunate and the neighbors around us very outgoing and friendly. Fun fact: Unbeknownst to us, our neighbor two doors down moved from the same apartment building in Victory Park right around the same time we moved into the neighborhood. We didn’t know each other at the apartment, but we remembered what each others’ dogs looked like, and we’ve since become good friends here. The neighborhood is also super-accessible to bike trails and White Rock Lake, which was another motivating factor on the location.

New house, after we changed up the landscaping.
New house, after we changed up the landscaping.
Raphael and I at the Dallas Arboretum, which is near our house.
Raphael and I at the Dallas Arboretum, which is near our house.

Everything in life has its tradeoffs. The thing I really wish I could do something about is the physical distance between where we live now and the rest of my family (that lives in and around Houston). When I graduated from college, I quickly became aware of how few opportunities there are in IT positions in the Houston area when I attempted to find something close to home. When I graduated, I had three different job offers and not one of them was in Houston. In the family I grew up in, just about all of my extended family lived and worked nearby where they grew up, close to family. It has really been an adjustment for me living away from family. My parents have always been my biggest supporters, but at times I can’t help but feel like I’ve lost or don’t have connections with most of my extended family.


I’ve come to realize that goal setting is important in your personal and professional life. Last year, I wrote a post on my theme and overall goals for 2018 and I’ve mostly stuck to that. However, what I didn’t talk about were some more bigger-picture items. One of these is Raphael and I are working to acquire investment properties (i.e. rental properties) with some of the appreciated Amazon stock that I’ve accumulated. At this time, we haven’t found a property yet, largely because the math doesn’t work in terms of what houses cost versus what they rent for. We haven’t given up yet, but we’ll probably keep looking until early-to-mid 2019. If that doesn’t work, we may start to look at other alternative assets to diversify away from the stock market. Pie in the sky goal for this would be to grow this into its own business that Raphael could manage full-time.

In 2017, I said that I wanted to be more deliberate with content creation. I haven’t made the time in my schedule to make that a reality. I did recently take up journaling for personal benefits, and over time I hope to turn some of those ideas into more public works (such as what I’m doing with this post). I honestly need to sit down and create a foundational schedule for my weeks since my personal and work obligations don’t leave me with much free time, and the free time that I do get could be utilized being more productive on personal goals.

On the career side, I haven’t decided what my next move will be. The one thing about Amazon is that there is no shortage of opportunities inside the company. What I do see a shortage of, however, is that most of the company revolves around Seattle and there are not many opportunities (that I haven’t already done) in the Dallas office. I’m happy with the city that I live in, so at some point, I may have to get creative with my next opportunity in the future. There’s always management or sales, but I’d really need to do a lot of soul-searching to make sure that is a long-term direction that I want to commit to since my entire career has been spent on the technical side.

Wrapping Up

When I set out to write this post, I had no idea that I would end up writing something so long. In fact, I actually had to force myself to remain focused on the core topics, since there is so much more I could write about. My goal for sharing this has been to share my experience for how I got to where I’m at, along with allowing me the chance to personally reflect on my experiences. Feel free to leave a comment below and let me know what you thought.