Jason Usdin currently lives in Stamford Connecticut with his wife Allison (also in sales), daughter Zoe, and Bernedoodle Rusty. Outside of work he enjoys tennis, fitness, cooking, swimming class with his daughter Zoe, and music (piano and Sax player). Making the adjustment from NYC life to suburb life has been fun these past few months for Jason and his family.
You received your masters degree in special education. How and why did you make the decision to go into sales?
It's funny, I come from a family of salespeople. However, during college I really found that I enjoyed working with children, which led me to becoming a kindergarten special education teacher and receiving my masters right after undergrad. While teaching, I was running a tutoring business and fitness business on the side. In 2015, I looked at the back of one of the textbooks I was teaching, and I reached out to the company to see if they were hiring. Lo and behold they were looking for a jr. rep to drive around door-to-door and sell textbooks to administrators in the state of NJ. I wanted to find a way to mesh my love for education and my passion for sales. I was always the kid who won the wrapping paper sales contest at school. Growing up, I would knock on every neighbor's door in my neighborhood until they bought something. It was a natural fit, and I was lucky that Houghton Mifflin Harcourt took a chance on a young scrappy teacher. I was still helping people, and learning sales at the same time, translating the patience I learned while teaching into a career in sales.
You sell professional services to help organizations with their AWS ecosystem (Amazon Web Services). Is it challenging for non-technical salespeople (non-developers) to sell technology to leaders/engineers? Any tips for other sellers who are in the same boat on how to overcome this and sell better?
From the outside looking in, it can definitely be intimidating. I was taking a course in Amazon Web Services (AWS) in 2017 because textbooks were evolving into platforms built on AWS. It was definitely challenging at first, but I had great mentors. I was able to shadow many seasoned Account Executives and managers during my first few months at Onica (my first AWS partner role in 2019). In addition, a requirement for onboarding was to pass the Amazon Cloud Practitioner test, which guides you in learning all of the 200+ Amazon Web Services, as well as the business value of each. With the cloud services constantly changing and transforming, there are always courses available to take to continue to grow technical acumen. The biggest piece of advice I would give anyone looking to go into a technical role with limited experience is to invest in the AWS cloud practitioner course and Amazon's free courses around the technical/business value of the cloud. And now with GenAI being today's hottest topic, I would highly recommend familiarizing yourself in that space as well. I am lucky that Caylent (my current company), invests in its employees, and gives us access to plenty of professional development.
What’s the biggest issue in your sales organization right now? Leads? Long sales-cycles? How are you working to overcome it?
The biggest obstacle is actually not within my organization, but it's actually more in my personal life. I recently became a father for the first time, and it's very important to find that work life balance, especially with a baby. Sales is a job where you are always on (nights/weekends — the hustle never stops). But after having a daughter, I've realized that even though speed matters and customers are always looking for that response right away, more often than not, they understand that family comes first. It's been an adjustment, but my customers and my colleagues have been very supportive. Sometimes that email that comes in at six or seven at night can wait — and it took me a while to learn that! Reading “If You Give a Mouse a Cookie” with my daughter is much more important. I am lucky that my manager has been supportive and guided me through this as he is a father as well.
How could someone get into a tech-focused sales role like yours?
Invest in yourself. In my opinion, technical literacy is more important in today's society than any other skill. Continue to surround yourself with modern technology and do not stop learning. Don’t be afraid to take risks either. I recently built an entire music video using AWS GenAI services with no skills in engineering. I did it all through watching a free YouTube course. There are so many free courses, YouTube videos, and even paid courses in cloud technology, and just modern technology in general. However, with that said, I cannot do my job without my engineers and technical team. I have a great support system, and I learn from them every day. Shout out to James B!
What advice would you give to someone who is just starting out and is considering a career in sales?
The best piece of advice I ever got was don't come sprinting out of the gates. It's very hard for salespeople to have patience. We all want that first sale to come through the door the minute we start our job. I remember my first sales call. I wanted to show my boss that I learned the product line, so I pitched every single product to the superintendent (science books, math books, literacy books, etc.). It was a disaster. So I would say, even though you know what you’re selling or THINK you know what you are selling , learn your pitch, practice your pitch, but most importantly: understand your customer’s needs.
