Jennifer Terrell

Being productive isn’t just about putting out volumes of work, it’s about organizing yourself to maximize your unscheduled time completing the highest priority tasks.


Jennifer Terrell of Nashville, Tennessee, is a lifelong student of the craft of sales and sales management. Rather than using her impressive academic pedigree from Purdue and Duke Universities to land a “real” job in the medical field, Jennifer continued her education at age 23 at the ‘school of hard knocks’ – taking a position as a 100% commission-based salesperson with no benefits… and she never looked back. That first job culminated in a 13-year run at that company, rising from an independent contractor salesperson to the most senior sales leader in the national organization, overseeing a sales force of more than 200 people. That’s where Terrell first discovered she was a builder of successful sales teams, and her passion ultimately led her to seek out other opportunities to start and scale sales for emerging companies and products. In 2010, Jennifer became the first sales leader to join a little-known startup called LivingSocial. 18 months later, with unicorn-status under their belt, Jennifer had helped LivingSocial grow to more than 300 sales people across 100+ cities and she was leading half the team as the VP of the Eastern half of the US and Canada. She became the head of Local Sales in 2013, managing revenues in excess of $1B, and oversaw a team of more than 500 sales team members, including hunter telesales and field sales teams, account management, and inbound sales channels before the company was acquired by Groupon Inc. in 2016. Jennifer remained with Groupon for 2 more years, where she was able to parlay her love of building sales teams from scratch, but within a large established organization this time. Working with marketing, product and engineering partners, Jennifer helped launch a new platform within the daily deal giant, and built a sales team of more than 100 people selling that product to local merchants across 23 cities. Recently relocated from Chicago to Nashville, Tennessee, Jennifer works alongside her husband JT Terrell, specializing in helping start-ups and growth-stage companies build their revenue-generating engines (coincidentally, JT is an accountability coach for senior leadership teams and his niche is in implementing the Rockefeller Habits to scale organizations quickly). Jennifer loves the exposure to entrepreneurs who are passionate about executing against their vision. Jennnifer and JT are also busy raising their two young sons, Hank and Mack, in their new Tennessee surroundings. They enjoy sports, their church community, and plan to someday have a family band.

Where did the idea for your career in sales come from?

When I first entered the field in 1993 it was never a career choice to pursue sales. With a degree in medical technology and a life plan to go to medical school I was looking for part time employment. The job market wasn’t great and I needed to work. With the advice from others who believed that I would be great at selling, I found a sales company that was willing to hire me and entered the field while studying to take the MCAT. I took a 100% commission-based job and in two weeks was handed a cheque for $1600, which was more money than I had ever made in two weeks. In the end I never took the MCAT and for many years I felt like my career in sales was sidetracking what I was really meant to do in my real profession, the medical field. But in the end I realize that I was lucky because my career in sales and sales leadership has been far more exciting and lucrative than it would have been for me as a doctor and I certainly have far less debt and student loans to pay off.

It is also much different today because sales is now a recognized curriculum in universities and I think that the career has much more prestige than it did when I signed up many years ago. Young people today can now evaluate their abilities, skills and passions, and be purposeful in their determination about whether they want to pursue sales as a profession. This has been great to elevate the overall professional, and it means that the talent in the field these days is much more skilled and sophisticated.

What does your typical day look like and how do you make it productive?

My typical day starts off with a plan from the night before which is laid out to maximize every minute of the day. Without this, I know that I would be able to accomplish very little. I use a combination of my calendar and scheduled meetings to capture both meetings and unscheduled things that I need to do for the day.

I use an actual system of productivity that I learned many years ago – it’s called ‘David Allen’s Getting Things Done’ system and it’s a way to make sure that you’re doing the most valuable and highest priority task at any given moment. It does take a lot of dedication to stick to the system and you have to block out time to plan every week. You have to make sure you schedule time for important things that are fundamental to your value system – like prayer, quality time with your children, and self improvement time such as reading. To some people it sounds silly to be so scheduled, but for me I find it is the only way to getting important tasks done.

How do you bring ideas to life?

Honestly, the creativity and ideas side of business has never been my strong suit. Where I excel is that I’m really a ‘doer’. My skill set is in bringing other people’s ideas to life. With my background in math and science I thrive in building the steps one at a time to create the process to get an idea into the implementation phase. It took me a long time to realize that this is my brand. I am an execution person; I take my executive partners’ vision and make it a reality.

What’s one trend that excites you?

One trend that excites me is the transparency around entrepreneurship, and the challenges of being in business as portrayed on shows like ABC’s Shark Tank. I love that the world can now see how common people are making the economy run every day in every way. I grew up in a small business family. My parents owned a hardware store and other kids thought we were rich because my dad was a business owner, but they had no idea of the stress involved in being able to make payroll every week and the amount of hours that my family worked. My dad worked six days a week and made countless sacrifices to be an entrepreneur. So it’s really exciting for me that the world gets a front row seat to on their TVs to appreciate the bravery it takes to set out and become an entrepreneur. I think that it has really helped inspire tons of people to make things happen and it’s also kept people from getting into trouble by trying to do something that they’re not mentally equipped to take on. It’s just an awesome education for entrepreneurship that previously didn’t exist and I think it’s really valuable.

What is one habit of yours that makes you more productive as an entrepreneur?

Easily the Two Minute Rule I got from the David Allen program. It states that if whatever task is facing you right now it takes you two minutes or less to do, just do it now. Get it out of your psyche, because to file it, delegate it, or put it on a list for later is going to take you more time than doing it now. Secondly the mental energy it consumes rolling around in your head is likely far more detrimental than the two minutes you lose by knocking it out.

What advice would you give your younger self?

Don’t do a reality show. Well, I say that because I did a reality show that lasted for one season and was part of the ever-popular ‘Housewives’ franchise. My professional brand took a real hit as a result. It shifted the conversation about me with executives, investors and boards of directors from “tell me more about how you are able to get such amazing results building these high-performing sales teams” to “why in the world would someone of your professional status with your accomplishments think it was a good idea to be on a trashy reality show?”. At my level, your brand is really everything, so I totally understood where people were coming from.

That being said, the choice for my husband and I to conceive and have my second son happened as part of the story line on that reality show, and I look at him every day and think he is the best deliberate decision I have ever made, so I guess I wouldn’t give my younger self that advice after all. Maybe instead I would say “pick your words wisely when you do that reality show, because internet video lives on forever!”.

Tell us something that’s true that almost nobody agrees with you on.

It is an advantage, not a hardship, to be a woman in the workplace over these last 25 years and that the majority of men are actually rooting for your success, not trying to keep you down.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Consciously remind yourself to show gratitude every day, to your boss, to your employer, to your employees, to your team members, and in my case to Jesus Christ. Remember how lucky you are to have the opportunity that’s in front of you today and make the most of it. Because I guarantee there is someone out there that is dying to take full advantage of the opportunities that you currently maybe taking for granted.

What is one strategy that has helped you grow your business?

Maybe not grow my business but certainly grow my career. I call it my strategy of drafting. Just like NASCAR you can get where you want to go by using an aerodynamic technique of capitalizing off of the reduced drag created by aligning with a leader car. I found that when I have stopped focusing on my own goals and instead align myself and my mentality securely to my bosses’ goals, and I mean waking up every single day thinking about nothing other than how can I make my boss successful, that amazing things end up happening to me. Not only is it a great working relationship, because what supervisor doesn’t love working with somebody who’s totally focused on their agenda and is loyal to them, but also when your boss’ career is elevated, it opens up opportunities for those beneath them and I have successfully drafted with almost every boss I’ve ever had.

What is one failure you had as an entrepreneur, and how did you overcome it?

I would say the biggest failure I had was with a startup that was offering me a lot of money to come build a sales team for them in an industry with a product that I knew in my heart was not a good market fit. I wasn’t mature enough in my career and didn’t have my value system as securely established as it is today and I took that opportunity, even though it was super short sighted. It wasn’t long before, regardless of the success we were having on the sales side, that the company folded due to vendors pulling their contracts. I had to justify that decision and those two years on my resume to every employer I talked to after that. I overcame it by being honest and it all worked out and I was lucky to find the next company.

What is one business idea that you’re willing to give away to our readers?

My husband and I used to be in the party rental business and we’ve often talked about the crushing expense that young couples face in having a great wedding. We would like to come up with a wedding expense sharing service where by coordinating dates and venues with other couples, they can afford to have an elegant event that is more cost-effective.

What is the best $100 you recently spent? What and why?

Leader Books which is a subscription service that provides handpicked books on leadership. But more importantly, it gives you a 21 day reading plan as well as an insightful guide on the books and how to use the information and actually implement it in your career, which is often the hard part for me.

What is one piece of software or a web service that helps you be productive?

Workflowy, which is a note taking app. It has replaced my Google spreadsheets, Evernote, and my notes app on my iPhone. You just have to use it for a week and I promise you’ll be hooked on it, everything from my meeting notes to my karaoke song list is on it.

What is the one book that you recommend our community should read and why?

Scaling Up by Verne Harnish. It’s for entrepreneurs who are wanting to grow and scale quickly, but it also has great simple business concepts that are applicable to use for small teams within larger organizations. Everybody can learn something from it.

What is your favorite quote?

“Hard work beats talent when talent doesn’t work hard.”

I feel like I have never been the most talented person; whether it be in sports, arts, or even in my profession, and I’ve certainly never been the smartest. But I think that knowledge has always helped push me to work harder than other people as a result. I heard that quote from a soccer coach when I was 14 years old and it changed my life.

Key Learnings:

● The fastest path to success is in helping other people rise to theirs and then drafting alongside
● Being productive isn’t just about putting out volumes of work, it’s about organizing yourself to maximize your unscheduled time completing the highest priority tasks
● Show gratitude every day – to your employer, your employees, your peers – as a conscious reminder to yourself to not squander the opportunity you have in front of you today
● The two-minute rule will change your life
● You don’t have to be the most talented person in the room, just don’t ever get outworked