How I went from Army Officer to Tech Sales Account Executive

I loved my time in the military.

There aren't many jobs where you get to jump out of planes, fly around in helicopters, shoot guns, and blow stuff up multiple times a year without paying out of pocket.

There aren't many jobs that quickly put you in leadership roles where you have anywhere from a dozen to hundreds of people under your responsibility.

There aren't a lot of jobs where you get empowered to train and mentor people around you. But… As much as I loved my time, I kept a solid foot in the civilian world, and many of my friends were in the tech and finance fields.

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I also was introduced to the

WallStreetPlayboys

known as

BowTied Bull

about a decade ago and was influenced by much of the writing.
It started with an article called
Everything You Need to Know About Choosing a Career

• Sales: You are paid for each sale you make. Each sale is an *event*

• Silicon Valley: The leverage in your financial model is equity the sale of the security is the *event*

• Wall Street: You are paid for each transaction closed *event*, or each position closed *event* and to a lesser degree each handshake that results in increased business *event*
  

But I figured - I’m likely not going to go back to school to become an engineer and build a startup. I also don't want to work 100 hours a week on Wall Street, nor go back to school to get an MBA at the moment.
So I decided if I wanted to make the most money post-military - Sales would be my choice.
My second line of thinking was, well, which sales areas make the most money?
Tech & Medical. Well, Medical sales can be lucrative. People will always be sick. There will always be new medical advances and equipment to sell… but I didn’t consider it as free a lifestyle. Medical Centers can often be in remote areas and require you to be physically present. If you go into surgical tech, you damn near become a doctor's assistant, spending hours in a surgery room.

Tech, on the other hand, will let you travel to some of the top cities lifestyle-wise: Miami, NYC, San Francisco, DC, etc. On top of that, you have a much greater potential to simply work remotely.
I made my decision to go towards tech despite having at least 2 more years before leaving the military..

Starting my own company.

Having multiple friends in the tech area. I was lucky enough to be surrounded by a lot of people in the crypto arena. I had been heavily invested in the ICO arena and eventually started my own company, essentially leveraging the military decision-making model in go-to-market strategies.
I worked with a number of companies and organizations - until the government finally stepped in and started asking questions.
The IRS, SEC, FinCen all were concerned with the business, and we ended up shutting it down and moving on. Crypto was a little too wild west, and we had an inkling of what was going down. I was still an officer, so I wasn't interested in getting caught in an investigation.

Fortunately, the skills I learned helped me a year and a half later as I exited the military.

At first, I assumed I would have to take a pay cut to SDR since I didn't truly have corporate sales experience. But I had a lot of experience selling and understood that a lot of military skills also translate into the sales world.

Working with autonomy
Back planning missions
Working “cross-functionally”
Times management
Leading your book of business
If you can show competence and build trust with a group of soldiers, you can do the same with a group of engineers directors, and C-suites


I prepared for about 4 months, researching the tech sectors, and crafting stories based on my military career that were relevant to their companies and studying for a couple of certifications. I also contacted and worked with multiple programs that were focused on helping veterans transition into tech.
Fourblock, Breakline and Tech Qualled are some great resources for transitioning veterans.

Most civilians are wowed by the military; I didn’t have to embellish anything.
When it comes to questions like "Tell me about a time when you set a goal for yourself and achieved it" and "Tell me about a time when you delivered results despite a challenging environment," they were easy and showed experience.

Secondly, I was extremely valuable to companies as a person who had prior experience working with blockchain, cloud, fintech companies at a more executive level than most.

Another thing that helped greatly was that I saved a large chunk of cash before getting out. Luckily, the crypto market and lots of overseas time savings gave me a massive stack of coins to live on.

Instead of needing to take the first offer to keep food on the table, I had the freedom to interview with multiple companies until I could find the best offer and negotiate higher.

Eventually, I landed an interview with a FAANG that was launching a new segment in a new city. They were building from scratch and needed people with experience building from the ground up. They valued the fact that I had both strong leadership abilities and had already completed a couple of the certifications they were looking for.

My first offer ended up being around 200k.
115k base
50k Variable
56k Sign on bonus
Along with about 150k worth of stock, I was given the chance to come in as a senior-level account executive, both to sell and to help build the organization, possibly transitioning into management.

*And I went above my quota that first year

Since then, I have worked at multiple companies, ranging from startups to field positions and enterprise (though I personally don't care for enterprise as much). I also utilize those skills to train and mentor other potential sellers and veterans looking to get into the tech sales industry.

While I primarily write about the travel space, feel free to contact me whether you are looking to break into the tech industry as a regular guy or a veteran. In the future, I may be launching more information on the industry and how to work remotely as a seller.