I remember getting to college orientation and being asked what I wanted to choose as my major. I was absolutely clueless. I had grown up on military bases, with my dad being in the Air Force and my mom working in various jobs at the bases on which we lived. Every adult I’d ever known was in the military or worked for the government. My perception of the work world was totally warped. Over the years the idea had been drilled into my head that once you graduated high school you just go to college to get a degree and then you get a job. At no point before the age of 17 had I been asked which degree I wanted and what job I wanted to get. I did not realize that this youthful indecision was setting me on a 15 year journey to sales.
The background
While at a loss for what career I should pursue, I found a creative way to delay that decision and promptly flunked out of school. I suspect this is partially because I had no idea what I wanted to do so was aimlessly taking classes and felt no drive to finish anything. And also largely because I was a relatively smart student in high school that didn’t have to put forth any effort to cruise through my classes and that lack of accountability did not translate well to college. Regardless, after three failed semesters of being pre-law (lawyer was one of the few jobs I knew existed) LSU politely asked me to not come back for awhile. I enlisted in the Air Force instead.
The Air Force taught me a lot; I’ll dive into those lessons on another post; I started to write them here but it was quickly turning into a novella. But the major lesson that I didn’t realize until I landed in a sales role was that my motivation is almost entirely dependent on my expectation of the outcome. If I believe the outcome is fixed or predetermined, I will give the absolute bare minimum effort. In scenarios in which I have direct influence, I’ll pour my heart and soul into it. It’s this character trait has me well-suited for sales.
After a few years in the Air Force I realized I needed to reboot life and get a college degree. I came back to LSU and took on life as a 26 year old college freshman. I still had no idea what I wanted to do, but at least knew the world was a bit wider. So wide in fact that I ended up declaring 16 different majors over my six year scenic tour of undergrad. In the order I can recall them I ran through: construction management, marketing, finance, economics, mechanical engineering, civil engineering, chemical engineering, petroleum engineering (you can see that progression), nutrition, kinesiology, pre-physical therapy, pre-veterinary, pre-law, history, sociology, business management, and finally back to economics. Those last three were the result of my panic around turning 30 and still having at least a year of school left; I needed to find the fastest path to graduate and make some money. I ultimately settled on economics as it was the fastest path with a respectable name.
As I was taking this grand tour of LSU majors I needed to keep some kind of money coming in so I worked for a delightful local restaurant. They were some of the best years of my life and I worked with some amazing people. I also worked with some complete pieces of shit. I’ll write more on all this later, but the short version is I had a blast there, it paid a ton of bills and allowed me to mature greatly as a worker. This was also my first real taste of the idea that the amount of work you do can directly correlate to your earnings, though obviously on a much smaller scale. I considered staying in the restaurant business but I have dreams of owning a beach house in Destin one day, and to do that I needed to spread my wings, stop being a fake manager, and enter what I still called the corporate world. I had no idea what job I wanted to do, but I knew I wanted to get one.
The hunt begins – the startup and the acquisition
Job hunting was hard. Despite the Air Force telling you how much companies value your military experience, it turns out that was an absolute lie. Hiring managers do like it as a point of conversation, but getting past the screening software to that step was tough. I found out later from a friend in HR that I was also terrible at resume optimization. As a result I spent several months looking for jobs but found there weren’t many companies looking for a random economics major with no relevant experience. This made me realize my destiny probably sat outside of Baton Rouge or New Orleans.
I weighed pros and cons of several cities, decided on Dallas, and set upon a job hunting extravaganza. I took some Adderall and applied to about 100 jobs in one night; probably three got back to me, and one of them was willing to hire me. It was a terribly run startup that had all the classic tropes of a bad company (I simply didn’t know what they were at time). It paid absolute shit, less than I was making as a waiter / fake manager at the restaurant but I didn’t care. It was a step in the direction I wanted to take. I moved to Dallas and got started.
I was 100% confident that no matter what the job was I’d be the best at it. I’d outwork everyone else, get noticed and get promoted. I realize this is often a myth in the modern work world, but I actually pulled it off. I ran circles around the people I was working alongside– not a hard feat as they were mostly incompetent or lazy. When the company was acquired just a few months into my tenure I got promoted to where I was finally making more than the Chick-fil-A employees down the street. As our organization evolved I got another promotion shortly afterward, still making pretty rough money but finally livable, while the work became increasingly oppressive.
The formerly [forced] fun startup had effectively shifted to a call center, and my role was evolving to where I was becoming a call center manager. No matter how hard I worked I couldn’t make any progress on metrics, and before long my job was just doing the documentation to get people fired. Though I hated it, this pushed me even further toward my first sales role. As I was commiserating with a colleague about the sharp downturn in work conditions, she told me about the company her husband worked for. It was a small pseudo tech company that operated akin to small SaaS operations. I wasn’t sure where I’d fit in there, but went through the interview process to learn more.
You eat what you kill
The interview was very open and ended with them asking me if I’d given thought to being in sales. I’d never really considered it before then, mostly because I had no clue what it really entailed. If I ever mentioned working over the phone my mother would screech “IT’S NOT COLD CALLING IS IT!?!” I believe she had a bad experience with a job at one point. I was really intrigued by the idea, but having no sales experience I had to first spend a few months with the product and the customers and get reps by upselling current customers. My role had me going all over the country to meet recently signed customers, training them, and identifying upsell opportunities. Business travel was fun for about three months and then realized why everyone eventually hates business travel. I was burning out on that quickly, but fortunately the time came for me to take over my own territory. The hunt was on.
“You eat what you kill” is the way the sales role was described to me, and it’s what got me hooked. This was a fascinating sales job; though it was an Account Executive role it was truly combining a sales development representative role with an account executive role. I got to own and develop a territory. I won some exciting deals, bent some rules to get deals done, and had some heartbreaking losses. I learned how to execute discovery, how to pace my prospecting, and how to run demos. There were a lot of the things the sales org didn’t do that I didn’t know existed yet, but this was a very solid foundation.
The company and product were actually a bit of a disaster, but honestly that made my sales process all the more fun. I developed relationships with my customers and peers that continue to this day. It was a fine job, but was focused entirely on the franchise automotive dealership industry and I needed to broaden my horizons a bit.
The next step
I had recently gone on my first ski trip and fell in love with Breckenridge, Colorado. I had a belief that I needed to be a man of the mountains, and when I was looking for jobs Denver was one of the first places I searched. I ended up with a great company that still has the most amazing office I have ever seen. This thing was 88,000 square feet of mid century modern decor with every snack imaginable all the time, along with a full cafe to cook us daily breakfast and lunch.
This sales job was also the first one for me to make use of a proper tech stack. If there was a tool to drive customer acquisition, this company had a vendor for it. We had a pretty solid product with a fairly respected name, and I was selling to small businesses which always has a pretty light hearted atmosphere to it. I was certain this was going to be my sales job for years to come, selling document generation and contract lifecycle management during the week and enjoying Denver and the surrounding mountains on the weekends.
The one hiccup in this plan is that I started that job in January 2020. I had about eight weeks to take in this amazing office, and then we all went home for two weeks to flatten the curve. Denver found itself particularly fond of lockdown policiess, and in early May they suggested this would go on for months longer. I was getting fat and quite unhappy in the city, so realized I needed to go to a place where I could live life a little more freely. As we were going to be remote for the foreseeable future I made my way back to Dallas and decided to figure out what to do with a return to office policy when the time came.
It’s worth mentioning that my manager at this place was one the worst managers I’ve ever experienced in my entire life. From day one I thought she hated me, and that was surprising given I’ve historically gotten along with managers unless they give me reason to not do so. No matter what I did I was always berated. She even set up our weekly meeting as “1 v 1” instead of “1 on 1” to properly convey the combative nature of our talks. Every week I felt like I was a boxer with his gloves up pinned in the corner just getting clobbered, hoping I kept my job until the bell rung. I found out later that every member of my team felt the same way, as did most of the company. She was a great seller but lacked the people skills to be a manager. Everyone that was there when I started left her team over the course of the year.
The upgrade and the sales life
As the months progressed and coronavirus started to ease its grip on employees being remote forever, my company started to tease the idea of returning to the office. This was not great for me as I was several hundred miles away and didn’t have the kind of relationship with my manager where we could work out a remote position. This was also when I was getting a litany of messages on LinkedIn from recruiters. These messages are quite common for salespeople, but this company stood out. After a couple weeks of interviewing I had secured a raise and a new job at an incredible company.
This is a true outbound sales role. If I don’t actively prospect and hunt, deals don’t come to me. I am competing with ~80 other reps for the same business, and it often comes down to who thinks the most creatively and acts the most urgently. I don’t get to sit back and wait for leads to send me an email and politely ask to buy. I have to think up every account I want to pursue, find new angles my coworkers haven’t, and be ready to make a deal when the customer is finally ready to move.
I earn a decent salary; far more in salary alone than I did just a few years ago, but where the earnings actually stand out is commission. While I don’t believe too much in the accuracy of sales math, there is some truth that if I spent all day every day prospecting and hunting I could make even more. Transversely, if I did absolutely no work I’d be out the door within a few months. This is truly the life for me, as my day to day actions have a direct impact on my paycheck.
People ask me why I got into sales, and I always tell them it’s because I didn’t want to do anything else. I really love the sales life.
