Thankful.ai’s McDermott has Expert Tips for Starting a Career in Tech Sales
I had the pleasure of interviewing Dillon McDermott, VP of Sales at Thankful.ai has spent the last 12 years working in tech sales. He’s spent time at early-stage startups as well as publicly traded software companies, and has experience as an individual contributor, sales manager and VP.
Thank you so much for joining us!
Awesome to be with you guys — thanks for having me!
How did you break into a career in tech sales?
My first job out of school was an AE at a technology publishing & software company — so I kind of jumped right into it. I wasn’t necessarily seeking a position in tech, or sales, for that matter. In fact, had majored in finance and was mostly looking for jobs in financial services in Boston. But, once I got an inside look at how technology companies operate, and the types of culture they foster, I was hooked.
In 2013, I moved to San Francisco and was thrown right into the thick of the tech scene. I was suddenly surrounded by so many companies that were innovative, full of passionate people and much more progressive than what I was accustomed to. I thought to myself — OK, this industry is for me.
What is the biggest challenge you see most new sales reps encounter?
I think when you join a new company there’s usually a certain sense of pressure to learn the product and market quickly. That stuff is important. But, people tend to think — the faster I can become a subject matter expert, or be able to answer every product-related question, the faster I’ll hit my number.
I always tell new reps — the first thing you should learn is how your solution helps the customer. What pain will disappear from using the product? Or, what benefit will they receive? From there, just getting really comfortable with discussing that — asking the right questions, sharing examples of how you helped similar companies, etc. Those are how you open up meaningful discussions that help you earn trust, and ultimately win business.
What is it that most excites you about sales?
For me, it’s always been about being able to compete. For those that know me, I’m a pretty reserved person. I’m not the loudest voice in the room, and many times in my career, I’ve had people tell me — “you don’t seem like a salesly person”….I take that as a compliment, by the way. But, despite not always being the most vocal, I am tremendously competitive. I always want to win, whether that’s out-performing the competition or my peers, or beating a benchmark I’ve set for myself. I love to compete.
Sales is always about raising the bar, setting new goals, going toe-to-toe with competitors and finding ways to win. Every day throws something different at you, and it’s fun being in an environment that constantly challenges you like that.
If you had to share, “words of wisdom,” with a new Sales Rep who’s about to start their career, what would they be?
A few things come to mind:
For one, use your resources! Sales is a team sport. The most successful (and consistent) performers I’ve seen are not the ones that know the product the best, or get by on charisma or their ability to “wheel and deal”. Being a good sales person is like being a quarterback in your deals. You call the plays and show others how to execute, but you will rarely win alone. Knowing when and how to leverage your teammates is key. It helps to open new doors, build credibility and solidify your deals.
Also, learn from your mistakes. Especially in the early years when you’re still figuring things out, it’s important to analyze situations and determine what you could have done differently. In this business, even the best lose more than they win. But what makes them the best is that they learn from their losses and figure out how they can avoid those situations in the future.
How can our readers follow you on social media?
Connect with me on LinkedIn! https://www.linkedin.com/in/dillonmcdermott/
This was very insightful. Thank you so much for joining us!
Thanks for having me, guys! Great to chat with you.
