Making the Transition to Sales Engineer Part 1: Started From the Bottom Now We’re Here

It’s official I guess. I am posting again after a self imposed, “I have no idea what to do with my blog now,” hiatus, since as you all may well know, I made a career change.

In the interest of full transparency, I still have no idea what to do with my blog now, but I also feel compelled to blog again.

So, for the time being, I am taking the advice of bloggers everywhere: “Just keep posting (you idiot).”

The Longest Disclaimer I Have Written To Date: Preparation Leads to Opportunity

I anticipate that this post may seem braggadocious. I assure you it is not my intention to show off here. I am simply stating factual things that happened and you can decide for yourself. I am thankful for the opportunities I have cashed in on along the way, and the wonderful people who helped to get me here. Always remember that whatever success we have in our line of work, we all stand on the shoulders of giants.

But, also, I would be remiss if I didn’t say that where I am now was not due to sheer luck and happenstance. There was a lot of hard work involved. I remember spending countless nights up until 2AM in 2001 learning how DNS worked, and AD, and DHCP. All while my now-deceased Maine Coon William slept soundly curled up next to my forearm.

William on my humidor.

I remember my first Sys Admin job supporting 14 employees at a non-profit where I was the IT department. I built computers to give to people with disabilities, which has been the most emotionally rewarding job to date . . . so far, anyway.

I remember installing/re-installing countless Linux Distros and setting up Samba and doing a Stage 1 build of Gentoo on my AMD K7 machine pieced together by a very nice vendor out of New Jersey who would frankenstein computers together at a discounted price for broke a-holes like me. And I did it so I would know the inner-workings of all the things.

I know what it’s like to manually meet dependencies for Linux applications. A skill that still comes in handy for Linux Admins everywhere.

If you want more of a rundown on my technical background, you can always read my post about it here.

I came up with my own learning system that allows me to learn things faster because I had to. Ask me about it and I will share.

I put my wife through nursing school by finding loopholes in the compensation plan where I worked at the time. And don’t worry, it was all perfectly legal.

I drunk-updated my LinkedIn profile on a whim in 2018 and hacked the keyword system that opened the floodgates for some very cool opportunities, one of which was another fortunate step on the way to where I am now. “Drunk logic” sometimes works, I suppose.

And along the way I have put in the time to hone my craft. And that’s really the first lesson I have for you: Always be honing your craft.

It also hasn’t been all rainbows and marshmallows. I have failed along the way too. Everyone does. Learning from your failures is literally how you grow. You deny your failures at your own peril.

At the risk of sounding all public-speaker-ish and eye-roll-y, preparation does lead to opportunity.

Let’s Go with the “Why” First

Gather round . . . tens of readers of my blog . . . and I will tell you a story. Why did I become a Sales Engineer (a.k.a. Solution Engineer or “SE”)? Well, my disclaimer is that I can only speak for myself. People are SE’s for a multitude of reasons. The other disclaimer is that I am only two months in and I could still crash and burn, but I seriously doubt that for reasons that qualify as a different blog post altogether.

But, the best answer I can give, is that I LOVE talking to people. Full stop. I love making them laugh. I love talking about the quirky hobbies they are into. I love solving their problems. I love whiteboarding. I love ribbing people. I love making SFW puns that get groans. The list goes on. Sure, the money is nice, and I’d be lying if I said that isn’t a factor, but it’s not the primary factor for me. In a way, this role is just an excuse to talk to people; I might as well use my skills to do just that.

To drive this home further, as discussed previously, I am not a great WFH kind of person. Don’t get me wrong, I love the option of working from home and I do cash in on it: categorize me as a “hybrid” worker who likes a good mix. If I have no human interactions face-to-face, I die a bit inside by the day. That whole idea of face-to-face interactions is a big factor for me.

Furthermore, I was fortunate enough to work for companies that are widely coveted by vendors, so I spent a lot of time with multiple SE’s and in more than a few cases, I was actually asked, unprompted, “Have you ever thought about becoming an SE? I think you’d be good at it.” And for a while I demurred. But over time, it became attractive to me for what I believe to be all the right reasons. I also learned what not to do as an SE from some of those experiences.

The Dark Side Part 1: Making the Decision

As I am sure many of you are aware, the running joke is that when someone goes from Engineer to Sales Engineer, it means they’ve, “gone to the Dark Side.” It’s a nice tongue-in-cheek phrase that I have come to embrace.

As with any other career change, making the decision to, “go to the Dark Side” was not easy.

I talked to people I know and trust who have been an SE for a long time. I drilled them on what the job is like, what the state of the SE business is in the long run, and ensuring my conceptions about the role are correct.

Furthermore, logic would dictate that if you go SE, you will never go back to what you did before. Why? It’s mostly math. It’s like, more money and stuff. Like potentially a lot more money. So if you cross that Rubicon, it will be hard to go back, unless you’re really good at holding back your finances.

And for me, not to sound all, “OMG IT’S FATE!” about this, but I feel like I was ready for this opportunity. I had all the right experience, I talked to all the right people, I found the right opportunity for me, and ultimately it was the right time in my life for this to happen.

The Dark Side Part 2: Notes on the “Dark Side” Running Joke

Good Engineers have what I would call a healthy skepticism of salespeople. In fact, isn’t that skepticism true for everyone? Who actually likes the used car salesman stereotype? You know, the douchebag salesman with the slicked back hair and the finger guns and the shiny tooth and the pinky ring?

Fun fact about me: I have worn a pinky ring since I was 16 because I idolized this guy, not because I am a Used Car Salesman or with The Mob:

Jason Newsted Pinky Ring

The way I see it, yes, there are evil douchebags who are in it for the money alone, and will bend or break the rules to make that happen.

I am not one of those people. I have the receipts. This job is not the first SE job that came along; I interviewed for others too that did not have the greatest of vibes.

As far as gauging your peers, the reaction from my in-the-trenches Engineer friends has been 98% positive. Many of them even supported me and said I would be awesome as an SE. There were a few who gave me the side-eye, or said, “Well, that’s . . . a choice.” And that’s fine. When things are rough for them they can always stay with me on my guest bed made of money.

How I Got Here

I have been working toward Sales Engineering my whole career, even if by accident. Maybe that’s some touchy-feely BS, but here’s what I am talking about, and this was my pitch in my interviews:

  1. I got my Master’s Degree in Information Systems Management (2000) – This gives me good business acumen: how to perform an ROI, basic accounting, how to match up solutions with business goals, and so on.
  2. I spent a long time as an IT Trainer (1999 – 2012). Part of my job as an SE is to train customers on solutions, or at least train them on the value of those solutions. Public speaking and whiteboarding is a big plus here.
  3. Switched to Engineering for-realsies (2012-2022), I spent time as a real-deal Engineer at two large Enterprise organizations. How did I do that? I literally went out with all of the Engineers to Happy Hour. Every time. Not kidding. I built rapport with them and I had the VMware/Linux skills to earn their respect. Once there was an opening, they brought me in.
  4. I got good at selling things internally (aka “getting buy in”) – As someone who automates all the things, there are situations where proposed automation has to be justified. And this is in a 360 degree fashion: Junior Admins, Peers, Management, and so on. How do you do that? A few things like, oh I don’t know, whiteboarding, Proof of Concepts, demos, training, people skills, diplomacy, and overcoming objections. You know, stuff that you do if you decide you want to be, oh, I don’t know, an SE and stuff.
  5. Started this blog and got involved with VMUG/VMWorld/Podcasts (2020-Present) – This gave me credibility for being in front of people. Not to mention this is part of a fortunate series of events that lead to getting my position as an SE. All of this gave me the receipts and credibility for what I bring to the table.

Advice: Going to the Dark Side

  1. Improve Your Business Acumen – I am sure everyone is aware of how awesome you are at engineering all the things. But if you don’t know why you’re engineering all the things and the monetary benefits as such, then you have some work to do. Know how to do an ROI and be able to make connections between the approaches/features of the software you are using/selling and how they can save or make money for the company. If you want to see what this looks like, you can take a look at one of my many receipts. Take a project at work that you have to sell internally and make it happen.
  2. Build Thy Network (of People) and Express Interest in Being an SE Now – I can’t take credit for this advice (thanks @JDWallace!). SE jobs are few and far between, so you have to be proactive. If you don’t have a network of people, you can start by getting involved with your local VMUG, or your local technical group of choice, or just plain say it out loud to people and stay in touch.
  3. Build Your Brand – Stay tuned for a post later on this one. I have a lot of opinions on this that qualify as yet another blog post altogether, so I shall refrain from detail and that phrase (“Build Your Brand”) probably means what you think it means. For now, just keep your Social Media Profiles up to date and we’ll talk later. That will be your homework!

Stay tuned for both Part 2, where I talk about my first two months as an SE and then a future post about how to Build Your Brand.

Hit me up on twitter @RussianLitGuy or email me at I would love to hear from you!

3 thoughts

  1. Love the content here! Really direct and engaging, can’t wait for part 2! Welcome to the SE world, I am looking forward to learning some things from your approach to this!

    Liked by 1 person

  2. Just come across with your blog, really it helpfull in many ways. I’m about to make a decision to change from Infra engineer to SE and your posting is helping me alot! thank you and keep going!


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