#KeepGrowing: From Retail to SaaS Sales: Growing Your Passion Through Sales

Growing through your sales career is just as important as advancing your career. For Ebony Wiggins, a Commercial Account Executiveat KeepTruckin, growth means challenge.From her first retail sales job at 16 years old to her current role in SaaS sales, Ebony is always looking for the next opportunity to grow and challenge herself.

During our conversation, Ebony stressed that she likes to challenge herself, not just with her job, but beyond her career as well. She challenges herself to do less talking and more listening, to get to know people a little better, to have real conversations and not to shy awayfrom hard conversations.

Q: You started your sales career at 16. You were so young! How did you end up in sales?

A:I like the challenge of sales. Both then and now, I always feel like I’m growing in this industry. In sales, every day is different and as an extrovert I enjoy the social aspects of the job. I like talking to people, getting to know them, and with sales, I get to do that and make money. I also enjoy the fast pace and go-getter environment of commission-based sales. I startedmy sales career at 16 years old, in retail, here in Nashville in designer liquidation, selling high-end overstock apparel. Customers were spending their hard-earned money, and they want to walk out looking fabulous. It was important to me to be honest with them. I have always sold with integrity, honesty, and tact – it is who I am at my core. I think this foundation has helped me have a successful sales career.

Later I worked in sales at Postmates, a food delivery service owned by Uber,  for about two and a half years. I was promoted four times while working on enterprise accounts with national brands like Potbelly, Chick-Fil-A,Cold Stone Creamery, andSubway. It was great to achieve that level of success, butI wanted to take my career to the next level; I wanted to do more.I wanted to get to know my customers, build a relationship with them and help them achieve their goals over an extended period of time. One of my friends shared her positive experience at KeepTruckin, soI decided to learn more. I joined KeepTruckin in September 2020 and it’s been a great experience so far.

Q: Tell me a little bit about your ramp-up. What was it like getting started at KeepTruckin?

A:The ramp-up period was excellent! It definitely exceeded my expectations.KeepTruckin hastools in place for ongoing virtual collaboration and communication. I was able to connect with the sales engineers for the demos, and sales managers are always available to offer solutions, navigate the sales process or the client buying journey and provide leadership and insight.My coworkers and other team members are ready and willing subject matter experts, there to offer help and assistance or just there to cheer you on.Also, KeepTruckin provides an incredibly detailed training program that got me geared up, ready to sell, and hit my quota.

Q: When you’re not selling or working, how do you like to spend your time?

A:So when I’m not selling and not working, I’m a Planned Parenthood activist, human rights advocate, andtravel enthusiast.I do a lot of advocacy work. I was a national speaker for Planned Parenthood and did a lot of lobbying.I attended the extraordinary Senate Judiciary Committee hearing in which Christine Blasey Ford accused Supreme Court nominee Brett M. Kavanaugh of sexual assault. I’ve spoken on behalf of Planned Parenthood, advocating for safe and legal access to reproductive healthcare. I’ve spoken at presidential forums, including the 2018 presidential forum, and had the opportunity to speak with Bernie Sanders.

I also spoke at the first-ever presidential forum that focused on reproductive rights. All of the 2020 presidential candidates were in attendance, includingElizabeth Warren, Cory Booker,and now President Biden and Vice President Harris. During the pandemic, I have spent more time on phone banks and virtual coaching with storytellers to register people to vote and encourage people to vote.

Q: That’s awesome! In terms of your career, what’s something you’re working on right now that inspires you, or something exciting within the industry that you’d like to share?

A: Something that separates KeepTruckin from a lot of other SaaS solution providers is that our technology is developed in-house, and it’s designed to ensure it’s easy to navigate. It’s easyfor the drivers to use, and it’s easy for safety and fleet managers to view, monitor, track, manage and ensure compliance. The ELD (Electronic Logging Device) rule – congressionally mandated as a part of MAP-21 – is intended to help create a safer work environment for drivers and make it easier and faster to accurately track, manage, and share records of duty status (RODS data). We focus on providing a complete solution: trucking companies get everything they need with the dashcam, and it syncs with that vehicle gateway, the asset gateway and tracking devices onthe trailers. All three of the devices can sync together and be managed and operated from one place, so I think that sets us apart.

Additionally, we are continually adding new features. We just launched the smart load dashboard, which allows drivers or companies looking for a load to pick up and dispatch. Drivers can go on to the smart load dashboard and find jobs for their drivers.

Q:It sounds fascinating to work withthese new cutting-edge technologies! When you think about your career and where you are, what’s the best career advice you have been given?

A: Make sure that whatever you’re doing, you do it with integrity. Also,put your best foot forward. Work with dignity, respect, and humility. It’s easy in sales to get a big head, but it’s critical to remember that you’re not any more important or any better than anyone else. Whether it’s a customer or a coworker, it doesn’t matter their position. Everybody deservesthe same level of respect, and everyone deserves to see the best parts of you. Ultimately, it always comes back to integrity which has been so critical and important for me.

Q:As you look back on your career, is there anything you would’ve done differently?

A:  Listen more. It’s something that my mom taught me, and sometimes it’s tough to do because I can be an outspoken person, but sometimes it really does pay off to just pause and listen. When I think back, there are some situations where I wish I had taken the time to listen. I have learned that I don’t always have to speak or add my opinion.  I’ve learned that things will work out and that sometimes it’s okay to just watch and listen.

Q: One final question for you as we wrap up our conversation: what’s one message you would like to send to our community that you haven’t had a chance to talk about?

A: One message I would like to send to other women of color in sales is: recruit, recruit, recruit! If you know someone you think can do this job, but maybe isn’t getting the right opportunity, reach out to them. Offer to help, make an introduction, or help coach them during the interview process. Whatever you can do, help another woman grow into a sales position.Be a resource for someone else so we can all see more diversity in our sales teams.


If you find yourself being the “onlyone” on your team, in the room, or the company, help recruit. One of the ways that we can stop being unicorns is to bring more people like us into the industry. Here is an easy way to get started. Please bring a friend, colleague, or sista in sales and join our #KeepGrowing virtual event!

Sistas In Sales & KeepTruckin are thrilled to invite you to a virtual experience to celebrate Women’s History Month. Join Sistas In Sales, the global leader for women of color in professional sales, and KeepTruckin, a unicorn SaaS company, on a mission to modernize the trucking industry on March 25thfrom 1:30PM – 3:00PM for a two-part experience – learning, networking, and recruiting. Register Here

In honor of Women’s History Month, let’s all choose to #KeepGrowing!

– Cherilynn

Chief Learning Officer, SIS

Cherilynn Castleman, Global Sales Keynote Speaker/Trainer/Executive Coach, has been a sales executive for 20+ years. With her natural talent for teaching and a drive to sell, Cherilynn uses her skills to coach and train other executives and sales professionals. Author ofWhat’s In the CARDS? 5 Post Pandemic Sales Strategies

Sistas in Sales, LLC (SIS) is a community for women of color sales professionals to network, advance their careers and most importantly, find sisterhood – offering events, thriving Slack community with companies hiring now, and career coaching services. Learn more about Sistas In Sales membership here, connect with us on LinkedInInstagramFacebook, and Twitter.

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