From Car Sales to Tech: An Interview with Nikki Ivey

Nikki Ivey started her sales career in 2004 as a seller for Budget Car Sales. She is the Director of Sales at Assembly, a company that is redesigning the way corporate teams come together by providing remote culinary experiences in the home. Along the way, Ivey has been a reporter, insurance salesperson, and social media manager. She recently co-founded SDRDefenders, an organization designed to help and support sales development reps.

I asked Nikki about what led her to tech sales, what advice she would give to sales managers, and her pathway to success.

How did you get started in sales?

Well, my background can certainly be described as unconventional. I was a teen mom, and let’s just say less than 1% of teen moms of color will graduate from a four-year college before the age of 30. What prompted me to get into sales was that I knew I loved communicating. I had an aptitude for it, and I also liked helping people.

I had a job selling cars, and a gentleman came in to buy a car from me. When the whole experience was over, he asked, “Why are you working 12-hour Saturdays? With your skillset? Do you know that you could be working in an office with regular hours, and they have snacks!” It turns out that he worked at a tech startup in Austin. The person who was the VP of Sales there at the time was Scott Leese. He hired me into my first tech sales job.

What did you learn about yourself in your first sales jobs?

As a new seller, and I think this is probably the case for a lot of younger sellers, you do find out what you’re made of. You find out what you’re willing to accept in a work environment and what your bandwidth is for the level of activity that’s necessary at that time. And you figure out either you want to do it or you don’t, and it can be an incredibly enlightening experience. So that was where I developed this love for prospecting, particularly at the top of the funnel — opening a conversation with a person and seeing how it can lead to good outcomes for everyone involved.

Tell me about the transition from car sales to tech sales.

The transition was about learning how to translate my experience and even the way I spoke about my experience. So, for instance, when I was selling cars, the bulk of my day was going on test drives. In tech I learned to talk about a test drive as a demo, because that’s the language that is spoken in B2B tech sales. That’s how I was able to get a foot in the door. I learned how to talk about my experience with car sales in parallel with a B2B tech sales role. I had a list of folks who bought cars three years ago, and now we were trying to get them ready to trade in. I did have a set number of those folks that I wanted to contact every day to see who I could get to come in. These are all parts of the sales funnel and prospecting.

What I think is an area of opportunity for the industry is that talented people who can enrich an organization often don’t know that such an opportunity exists. I only got that opportunity, because someone came and plucked me from obscurity and said, “Hey, this is a thing that you can do.” And sometimes what you see in your environment can affect or limit what you think you can do. I didn’t know any black people who were in the tech industry period, let alone sales. Because of that, I thought that the qualifications were going to be more outside my reach than they were. I discovered these are simply people with ideas, just like me, and that really boosted my confidence and made me feel like this is something I can do.

Now, through my SDRDefenders organization, I’m working on coaching and supporting SDRs, people who are just beginning their sales careers. I’m also working on attracting folks who might be out working some retail job and, like me, can be plucked from obscurity. And I’m working on attracting more of those folks into the profession. I’m doing that with the SDR Defenders and Sales for the Culture. I also did it through a black-owned consultancy that I worked for, called The Cultured Perspective. That’s where I got to coach for growth beyond just the SDR seat. This includes areas like teaching organizations how to build strong employer brands and employee advocates through empowering their salespeople and building their personal brands as well. Many people seem inauthentic when they’re trying to build their brand. It’s tough to know who’s a credible source to learn from, and, if I’m trying to build my own brand, do I imitate these folks because they are getting accolades and being called influencers? Who gives them that title? I liked to coach on this theme of authenticity. You have to talk about what your experience is in order to set yourself apart.

What has been your biggest challenge in sales?

My biggest challenge coming into sales was deciding if I wanted to be liked by my peers and leaders or respected by them. And that was a challenge, because when you come into an organization, feeling like you belong energizes and motivates you, and you can mistake the kind of attention that you get for that, and the way people respond to your likability. I almost fell into a trap of letting myself become a mascot, somebody who’s great to have on the team, because I’m fun to be around, but not actually putting in the kind of work that earns respect and builds a career. Early on that was a stumbling block for me.

Additionally, when someone new comes to your team, it is easy to be hyper competitive toward that person. I’ve done this myself, and I’m not proud of it. “Oh, I don’t want them to shadow me. And I don’t want to have to teach this person, because I’m trying to get my number and all of that.” But if we decided to take the opposite approach and pour into other people, the way that we needed someone to pour into us, that’s how we affect change beyond the bottom line.

What’s your advice to others you want to be successful in sales?

Be curious. You need a genuine curiosity about who you are and what you can accomplish. In other words, you need to enter it without expecting an outcome, other than learning about yourself. Opportunities and successes will come, just be patient.
Pay attention to how it feels. For instance, how does it feel when you get hung up on a bunch of times in a row compared to when you win your first deal? Learn that there must be a balance in how you react to both of those situations. When I was able to do that, and to apply that to other parts of my life, it was impactful.
You are stronger than you think. A lot of my life experiences were already building up in me, the type of grit and work ethic that makes people successful in sales. As a teen mom, I was in the situation where you have got to have grit just to survive — it’s character building. And sales helped me understand that’s something that can be applied in other environments, to help other people, to help myself, and to help your organization.
Communication is key. I have learned that the conviction with which you are able to communicate ideas is very valuable. Conversely, I used to consider a lot of what some would call my “soft skills” or intangibles as less valuable because they come naturally.
Be yourself. Don’t discount the charisma, effervescence, and charm that you have. To an extent, when you get into sales you sometimes must perform with more than what your sales and product knowledge might give you. Meaning you must apply all your skills and allow them to work for you as well. These traits make this work even more fun and that can be a differentiator in this field.
Don’t compare yourself to others. I beat myself up when I didn’t get the results that the person next to me was getting and, at the same time, I could get a little bit arrogant when I was getting better results. That really held me back, and neither position was productive. In retrospect I would have spent less time comparing myself to other people.

How have you built your confidence?

My mom always told me, “Let them tell you no, instead of you telling yourself no.” Challenge the stories you tell yourself about what you can and cannot be. Silence the voice that says that you don’t belong, because everybody in the room doesn’t look like you or has a similar background. That’s not the case. The case is that you’ve belonged the whole time. They might not have been looking for you, but that’s okay because you found them. So, walk into that room and own it.

You can do it. And most folks who are successful in their careers now as sellers tell me that they wish they had started sooner. And that’s exactly how I feel, because when you start sooner, usually you’re going to learn more quickly when the stakes are relatively low. And at the same time, you set yourself up to be ahead of the game in terms of building wealth. And that’s incredibly difficult to do in many other industries right out of college and especially without a college degree.

What’s your advice for sales managers on building diversity?

I would tell sales managers to have a tough conversation with themselves about whether they’re really doing everything they can to democratize access to this industry. Are you being stewards or are you being gatekeepers? So as a steward, it is incumbent upon you as a sales leader to be looking as far and wide as possible for the best person for the job. For example, say you’re a Silicon Valley tech startup. If you’re only looking for folks in that environment who graduated from the same Ivy League schools, you can tell yourself that that means you’re getting the best talent, but how can that be true when you’ve significantly narrowed the pipeline? I would say first widen your aperture. And I would say to view the new people who you’re inviting into your organization as the pipeline for the future of your organization. If you do that then people will be more likely to stay, and you won’t lose money to attrition. People will be more engaged and will feel more included. All the numbers say that this will make you more profitable.

Another competitive edge that an organization can have is an effective sales culture. This is increasingly important for new and younger sellers. The willingness for certain organizations to advocate for one group or another can affect your ability to attract elite talent. Diversity is only one piece of the organizational culture. There’s also this element of initiation in sales, let’s see if you can handle this environment, sink or swim. Therefore, I do so much work supporting SDRs. They might tell you to make two hundred calls using a Rolodex, and you’re talking to people who never saw a Rolodex. So why would you say that and expect them to perform? So yes, I would say an effective sales culture is not just a key differentiator for organizations to attract better talent and avoid costly attrition, it is a way to make a significant impact on society.

Do next generation sellers have some advantages?

Next generation sellers bring an optimism and enthusiasm about not just their own futures, but about the future of the world. In a typical tech startup, often the founder is just really jazzed about the tech that he or she has built. In my experience, when you walk through that door, you’re being inspired and compelled to believe that the work you’re going to do with this organization is going to change people’s lives. And I think that this generation that we’re talking about is particularly good at that. They have opened their minds and believe that they can have an important impact. That kind of conviction cannot be taught.

Why do you think comfort with technology is crucial for sales success?

While this generation of people will often come into an organization already having a high level of comfort with technology and had screens in front of them all the time, many grew up without a computer in the house. While a lot of folks will diminish the importance of that fact, we live and work in a time where digital presence is a force multiplier. The key differentiator is to have as many folks as you can in your organization who are comfortable with technology. That way you set the stage for a future of success in sales.

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