Q&A With Jennifer Terrell, Former Sales Executive at LivingSocial and Groupon

Jennifer Terrell

Jennifer Terrell is a former Sales Executive at LivingSocial and Groupon. She earned a BS in medical technology from Purdue University before completing her clinical work at the Duke University Medical Center. But the bulk of her education, as she describes, is from the school of hard knocks. Terrell considers herself a life-long student of the crafts of sales, sales management, and sales leadership. For the past decade, Terrell was a sales executive in the online retail space, and helped scale the daily deal industry into a global marketplace. She now specializes in helping startups and growth-stage companies to build and scale their revenue-generating teams. Jennifer lives in Nashville, Tennessee with her husband JT and their two sons Hank and Mack.


Where did the idea to enter the sales industry come from?


Back when I entered the field in 1993, most people came into it by happenstance. I had gotten my degree in medical technology had done my clinical work at Duke University Medical Center, and my life’s plan was to go to medical school. I moved home and was studying for the MCAT, and I started looking in the newspaper for part-time employment to get me through. I saw an ad for a 100% commission-based sales job, went in for the interview and got the job. I was working there for two weeks and made a ton of commission plus. It was pretty shocking to me the amount of money I just earned.


I think there was a bit of divine intervention because right around that time, I was seeing a neurologist for a medical issue I was having, and we got to talking about my pursuit of the medical profession. She said to me “just be sure that you’re going into the field for the absolute love of patient care, and because you want to help other people above all else”. She also added that “you are going to have at minimum of a decade doing a lot of things that don’t look anything like prestigious doctor work, and you’re going to get out of school with crushing debt, and don’t even get me started about the business side of things and how hard it is to make money while giving the appropriate amount of time to your patients”.


I remember walking out of her office and doing the math of my head about how much money I had made over the last two weeks versus the amount of money I’d be making over the next 10 years. It became clear to me after that conversation how absolutely passionate I actually was about selling. I was good at it. I wanted to get better at it. I couldn’t stop reading and researching and learning about it. Here we are two decades later and I’ve been lucky enough to have held executive level positions at major disruptive growth companies, and have hopefully been able to inspire hundreds of young sales people entering the profession over the years, all because of that timely conversation I had with someone who encouraged me to only pursue something that I was truly passionate about.


What types of individuals are successful in sales?


Recruiting for sales is really tough because the qualities that people need to be successful in the field are qualities that are really difficult to uncover in an interview. There have been hundreds of books written on the ideal profile of a salesperson and how to uncover those underlying characteristics. But in my experience you could line up the top performers I’ve had on my team at five different organizations and you won’t be able to find a pattern in terms of education, background, etc. I usually look for a couple of different things if I can identify it:


First there’s disciplined self-starters. A lot of times a military background or people who’ve been working from a very young age, like waiting tables at 16 or cutting lawns at 13, are the candidates who always catch my eye.


Secondly, I’m looking for people who thrive off winning. Competitors… athletes in high school or people that played college sports usually stand out to me as well.


Number three is people who are more process-oriented and focused on outcomes as a result of moving through steps A to Z, which is a really different quality than you might think I would want for a salesperson.


In your opinion, what does the ideal company culture look like?


As I’ve always had the luxury of being in the sales industry, I can tell you that sales teams will establish their own micro culture within the broader organization’s culture, no matter how much you might try to prevent it. I look at my job as a sales leader to make sure that the two cultures don’t run counter to each other and that the sales culture is a healthy one, as closely aligned to the company’s values as possible. And that’s not always easy, because high performing sales people a lot of times aren’t great collaborators. I always try to keep a couple of themes central to the sales culture most. Number one is transparency, always being open with communication, understanding how what they’re doing is impacting the business, and tons of recognition and growth.


Ownership and performance is very important too. The best thing about sales is that we can be measured, in terms of awards and incentives and commission. And I would say the worst thing about sales is that we can be measured, but it’s important to understand that and to take accountability at all times for your performance… when it’s good, and just as importantly, when it’s bad.


What is the single largest problem facing online retail companies today?


Customer acquisition on the demand side. I’ve always been fortunate enough to be on what we call the supply side and it’s relatively easy to get merchants and suppliers to understand why they need to work with you and to sell them on the idea that you can help them move their business services. The hard part is actually delivering on that promise by bringing enough eyeballs to your site and enough buyers to the table so that your suppliers get results. A marketplace model is a really tricky business to be in and I’ve always had a tremendous amount of respect for my internal partners who have the responsibility for the customer acquisition side of the equation.


What have been your top professional accomplishments in the past five years?


Certainly holding the Head of Sales role, overseeing more than 500 sales people at a billion-dollar company has to be up there with the things I never imagined happening to me when I was 18 years old. I’ve delivered several keynote speeches in front of hundreds of people, including LivingSocial’s Annual Conference at the Gaylord Opryland, and the CardLinx Association Conference in New York, which I had never envisioned in my younger self. The successful launch of the Groupon Plus platform for merchants was a labor of love that started with a concept and ultimately resulted in a product that came to life and is now being used by thousands of local merchants.


That was my first experience being involved in a product launch more deeply than just on the sales side. Seeing that it takes a concentrated effort from so many smart and hardworking people to make something like that happen was an amazing experience.


Most recently, helping my husband launch his very successful Petra Consulting practice. My husband JT Terrell is an accountability coach for senior leadership teams and specializes in implementing the Rockefeller Habits to scale organizations quickly.



What are the most important personal satisfactions working within sales?


Well, number one is job security. I never have any anxiety about how I’m going to be able to afford my family’s style of living, because I 100% dictate that. It’s totally freeing to know that you can simply make money at will because generating revenue is your skill set. There will always be a company that needs your skills. I think that sort of fearlessness comes from having worked in 100% commission sales for the first 13 years of my career. I joke that I’ve been flying without a net most of my life and I have yet to hit the ground. So now in my leadership career, I would say that the personal satisfaction comes from helping other people new in the profession to develop their skills and reach that same realization that they are in total control of their financial destiny.


What does your career path look like and how did you get to where you are today?


I wish I had some secret advice. I’ve always been of the mindset that if I just do the job that’s in front of me, and completely knock it out of the park, that good things are always going to happen. I honestly have never been the type to be thinking about how can I get promoted or what can I do to position myself for the next opportunity.


I know that sounds crazy, but it’s actually worked out for me to just focus on what’s in front of me at the time. Every opportunity that I’ve had, someone has always approached me and said, “I’d like you to think about doing x because we think you’d be great at it”. Maybe it’s because specifically in this current environment of everyone needing immediate gratification, everyone wanting to get promoted, employers find it refreshing to have someone on the team who is just solely focused on doing well in their current role and being supportive. I think that makes them want to give me more responsibility.


What is the ideal experience for a customer/client?


You know, I think the age old saying is still true and I tell my sales people this all the time: quit selling and focus more on the relationship. Under promising and over delivering… that’s the ideal experience we want our customers to have.


Can you share some career advice to others?


First is to figure out your ‘why’ sooner rather than later. If your entire purpose in life is to make a ton of money, that’s fine, know that’s your ‘why’ and that you’re going to sacrifice some happiness and some job satisfaction considerations along the way. And vice versa: if you’re super passionate about a certain path that is never going to be lucrative, make a conscious decision early and just be solid with your decision. Remember why you’re doing what you’re doing every single day because if you’re conflicted on your why your career is always going to be a rocky road.


Secondly become a great communicator. Great communicators are in short supply these days and there’s a wealth of information available to help you become an effective communicator. If you can master that skill set, this will do more for your career than anything else I can share with you, and it will also help you in your personal life.


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