From Account Executive to Sales VP of a Billion Dollar Company — Here's How

Nine months ago I was hired as the VP of Global growth Sales at a billion dollar tech company. I'm responsible for driving tens of millions in annual revenue while leading three separate sales orgs. And not that long ago I was completely convinced I did not want to be in sales. I actually accidentally got into sales and then I absolutely sucked at it for two years. A big part of my early struggles were tied to my personality or at least my perception of my personality. I've been an introvert my whole life and because of that I I wouldn't be able to become a world class seller because all the great salespeople I saw seemed to be natural extroverts. I was missing numbers. I was watching all of my friends and peers promote fast while I was stuck. I didn't realize it for quite some time. It wasn't my personality that was slowing me down. It was my own mindset that was literally killing any chance I had to become good at sales. Now looking back at my career, I've noticed many ups and downs that I've had and how I could have saved so much time if I would have just known how to do a few few things right. So in this video I'm going to do a small breakdown of my journey starting as an SDR all the way to vp so you can hopefully scale faster than I did or simply learn how to be a better seller and leader which I guarantee will help you make more money, hit your goals and top the leaderboard. Now I when I landed my first role by accident because I thought I wanted to be a consultant, I did an internship and I hated it. So when a small startup recruited me and I went in for a SDR role, I was very reluctant. I literally told the co founder of my final interview I didn't want to be in sales. He said it's fine, you can, you can start in sales and then change later. You'll just make less money. So I took the role, planning to change later and then after just three months as an sdr, I promoted to be an AE despite not being ready for that role at all. That was a really tough two years. I even remember 1/4 being at literally $0 on the last day of the quarter which is a miserable place to be as an ae and I closed like a really small deal to finish around 10%. I was having a lot of self doubt. I was making excus and I was constantly comparing myself to others and why I wasn't doing as well. When I saw my friends doing better, I would dig in to how they were doing it, but not in a way to help me get better. In a way to help me feel better about myself. I'd say, oh well, they've got better customers that upgrade. Of course they're closing more or they're they're getting better inbounds than me. I basically had 30 reasons why I wasn't doing as well as them and I had convinced myself that none of them were my fault. I remember having a one on one with my skip level manager. So my manager's boss or he gave me a piece of advice that completely changed my career. He said, you got to run in your lane. I was so worried about what others were doing that I wasn't able to run in my lane. I realized that every minute I was worrying about how somebody else was having success was time that I wasn't working on my own. We've all heard the the phrase that comparison is the thief of joy. I also learned that comparison is the thief of productivity. I also realized that I was emotionally hedging. I was convincing myself that I wasn't having success because I wasn't in the right situation, the right territory and even more dangerous, I'm not having success. But I could if I really tried. I was afraid to completely commit because it's a scary thing because if you completely commit to something, you're forced to take accountability if you still fall short after doing all that you can. So my first step was committing to myself that I'd sprint in my lane and do everything I could to get good. Which meant I had to start obsessing over skill development across every role of my career. I've had to learn critical new skills to continue to progress as a Junior ae. I had to learn how to run full cycle deals because as an SDR all I had to do was sell the first medium. The transition to AE took me those full two years before I was comfortable running full sales cycles. Now there were three skills I had to master to get good at the Junior AE role. The first one was confirming that we had found a real pain worth solving before moving on from discovery. No longer spending time on super superficial issues. The second one was finding additional people in the account that might benefit from our solution to build momentum across a wider base. Not just relying on my one champion to bring the deal home. And then the last one was making sure that my demos were no longer high level overviews, but rather showing the customer exactly how they'd use our product in their environment for their use case. As I did these things. I finally hit my groove as a junior AE and I promoted a couple of levels into a senior AE role. My deals in this role started getting much bigger when I began getting higher in accounts earlier rather than waiting until the end. As a junior ae, I wouldn't get execs involved until it was time to sign the agreement. As a senior AE closing much bigger deals, I learned to get them involved earlier to define the solution, drive the value and access larger budget. I also learned the so what? Test, which is the idea that when my champion presents to a CFO or a CEO what the value is, they had to answer a CFO saying well so what? What is the value to the business, not just what is the value to you? I was then promoted into my first leadership role when I showed two skills. I demonstrated an ability to teach others how to sell and my process became repeatable. If you want to go into leadership, you have to be able to answer the question how are you having success? If you can't define it, you can't teach it. And by the way, if you want to take a deeper look inside inside my sales brand, I do have a newsletter where more than 16,000 people like you are getting weekly drops of my best knowledge and you can get that link in the description now. After after several years leading sales orgs at Qualtrics, I realized a new challenge that was killing my growth and progression. I realized that I only knew how one company operated. For me to hit my potential, I needed to put myself in a new environment and a comfortable environment to stretch me, which led to me taking a smaller job at MongoDB. I went from running 10 teams and more than 60 account executives to running only three teams. But it was a more technical product, a company with more rigorous process and an opportunity to get into the DevOps space which is one of the fastest growing and most relevant industries today. That step back in my career paid off in a massive way. After spending two years at MongoDB, growing my role from leading just a couple of teams to leading North America for their high tech acquisition, org launchdarkly recruited me for the largest role of my career, an opportunity to lead global sales orgs and multiple functions. I never would have had that opportunity had I not left Qualtrics in a downward move into a more complex sales environment to expand my skill set. I've been fortunate to have a really fun career so far. I've won AE of the Year, Manager of the Year, RVP of the Year, and most recently VP of the Year plus several other awards at every company I've worked at so far. But I love to reflect on how I started because I didn't want to be in sales. And then I sucked at sales for more than two years before anything started to click. My slow start is a big part of why I love to teach sales. I firmly believe that sales can be learned. You aren't born great, and I absolutely know this. True, because I wasn't. Now, this is just a small peek into my story, but if I could summarize all of my most valuable lessons in one place, it'd be in this video right here. In 10 minutes, I can show you the most value I've ever given on YouTube so far, so I'll catch you there.