EPISODE 490: Being Fearless in Sales Conversations with Women in Sales Leader Kristie Jones

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[EDITOR’S NOTE: This is a replay of the Women in Sales virtual learning session sponsored by the Institute for Excellence in Sales on March 22. 2022. It featured an interview with Kristie Jones, principal of the Sales Acceleration Group.]

KRISTIE’S TIP: “Be fearless in speaking up and saying things are not okay in a way that you can be heard. It’s not about stomping out or raising your voice. It’s about, “Hey, you’re probably not even aware that this happened in the meeting, or that you made this comment that made me feel small and invisible.” It’s our job. We are going to have to support each other. We’re also going to have to have uncomfortable conversations in order to help move it forward. No change in our country and other countries have happened without having uncomfortable conversations happen.”


Gina Stracuzzi: Kristie Jones is the principal for Sales Acceleration Group. She’s going to tell you about herself and then we’re going to dive into the really juicy stuff. Kristie, welcome.

Kristie Jones: Gina, thanks so much for having me on. I spend my days helping mostly tech startup companies. Companies that probably have received some series A funding, helping them build out their sales process, their sales strategy, in a lot of cases, helping them actually hire their first few sales reps, SDRs, BDRs, AEs, and customer success. Making sure that, again, that stuff gets sticky. I spend most of my time helping them focus on building top of the funnel. If we can’t sell anything, the pipeline is empty.

Gina Stracuzzi: Talking to you offline a little bit beforehand, I know that regardless of whether you’re a startup or a large corporation, you have knowledge and insight that everyone can use. That’s what I really want to get down to. Let’s talk a little bit before we get into all that about how you got started in sales and how that shaped you moving forward.

Kristie Jones: I grew up in a sales family, first and foremost. That definitely I think gave me an advantage. My family owned a Coldwell Banker franchise, a real estate company. My father was the owner broker. My mother, after 18 years of teaching English and Spanish to high schoolers, got her real estate license over one summer and then never looked back. She then began selling real estate. I affectionately say to people I got my MBA at the kitchen table, because even though my parents worked in the same office, they never saw each other. Catch up time always happened over dinner, if my mom wasn’t out listing a house, or selling a house, or presenting a contract. I have a younger brother, and so he and I were the beneficiaries of getting to hear a lot of things about business at a very early age.

My family was always very transparent about finances as well. I knew when my dad was and wasn’t taking a salary in order to ensure he was able to make payroll. I knew what my mother made on every single house that she sold. Money was very transparent in our family. Then really the issues that my dad faced as the leader of that organization and the issues my mother faced as a top sales rep in a very competitive industry. She says, “There weren’t a lot of friends around. You said hi in the hallway, but those were your competitors.” Unlike other situations that I’ve been in where everybody can win, because everybody has a territory, when you’re selling within a geographic region in the city that we lived in, everybody was, even people in your own office were competitors.

I know that that really shaped where we are today. I ended up taking the sales leadership path that my father had positioned for me. My brother happens to be very, very successful, one of the top four sales reps in his company. He took the individual contributor route like my mother. I have no doubt that that kitchen table conversation that we had day in and day out shaped who we are and the areas that we chose. Ironically, my brother and I would never switch spots. He thinks I’m crazy, I think he’s crazy. But no doubt, I saw the ups and downs of businesses, I saw the challenges my mother had as a female salesperson. I also saw how my dad handled and managed both genders. The influence there was definitely critical and has shaped how I operate and how I treat others.

Gina Stracuzzi: That’s remarkable. What an opportunity too, because in other fields, there might not be as much as you could glean from the conversation. If your parents weren’t in the same field, they wouldn’t have been having that level of conversation. That really is an MBA sitting there. Hats off to your father that he made sure everyone else got paid before he did, which can be tough on a family, but that’s good leadership for sure. Let’s talk a little bit about the startup environment and how that is for females, and if you see some of the same issues that can sometimes plague a corporate culture.

Kristie Jones: I think it’s everything from female founders are not getting the level of funding that male founders are getting. It starts there. In the six years that I’ve been consulting with founders, I have yet to work for a solo female founder. I’ve worked for women who had male co-founders, but in working with probably 60 plus, 75 plus companies over the last six years, I’m still waiting for my first female founder to show up that I can work and support.

First off, in my world it starts with the money. The people who have the money are mostly men in the VC world. We need successful women, whether they be in corporate environment or whether they have a family business, we need women to finance and support other female founders. Because we’re just not getting that kind of funding from the male VC dominated world, and the PE world. I think that’s always my first disappointment. Again, I love working with my male founders, and they’re all super smart, but I think it’s hard. I think it’s hard for women in tech to be present and to be there in force when they don’t have a lot of role models.

Gina Stracuzzi: I have read about groups of women who are trying to change that, trying to start some VC rounds themselves. I’m sure banks don’t make it easy. As you say, it’s still a man’s world in that respect. What are some of the lessons that you see when you’re working in this world that perhaps women who are in startups, and this is really relevant to women in corporate worlds too, see some of the difference? How would you suggest that women capitalize on those differences so that they can really move beyond the stigmas we just talked about, the things that hold us back regardless?

Kristie Jones: Women in general are relationship oriented. Maybe not as competitive as men seem to be, but when you look at some of the statistics, women, and particularly in tech, are as or more successful than their male counterparts as far as hitting quota, relationships that they’re building. I think as a sales leader, when you’re building out a team, you need diversity. It makes everybody better. It’s going to provide other points of view, but women are going to have to start advocating for themselves. I take a little bit of a different stance. Yes, I’ve got some suggestions about how men can help women in a sales environment, but women are going to have to help themselves. Then they’re going to have to get over some of the stereotypes.

I shared with you early on, before my mother became a real estate agent, she spent 18 years teaching English and Spanish. If you even go back to that generation, which isn’t that long ago, my mom’s still alive and in her mid-70s, you were a nurse, or you were a secretary, or you were a teacher. Even comparing it to the minority situation and going all the way back to slavery, how long it’s taken minorities to get somewhat equal treatment, I don’t think we’re there yet. But when you think about the fact that women, even if they went to college, they came out of school into very segmented professions. We’re a little behind the eight ball, we’re still a little behind the eight ball. Women are going to have to advocate for themselves. Women are going to have to go out there and not only promote themselves, but also promote other women, support other women.

One of the things that I do, and people ask me about this all the time, I’m a junior achievement instructor. I teach second grade and seventh grade. Second grade, it’s all about our community. One of the reasons I support junior achievement and I’m a volunteer is because every one of their curriculum at every grade level has a financial piece of it. Financial literacy is such a challenge. Women have got to get comfortable without earning their partners, their spouses, without earning their male counterparts. Getting more comfortable with just money in general and having those conversations and not feeling badly about out-earning men that are in their world.

In that little second grade class, we do my community and I give everybody a little bit of money. Everybody picks a business that they want to run. Then they go and buy things from everybody else. They go to the pizza place and get a slice of pizza. Then they go to the florist and they buy a flower. One of the reasons I do that is I want little girls to see, and I tell them about what I do, and I tell them about my business, and I empower them. I have a very strong personality and I want them to know that it’s okay to go into sales. I want them to know it’s okay to have conversations about money. The seventh grade curriculum I teach is on international business, about tariffs and things like that. I think exposing girls at a young age, and all along, and supporting those to let them know that, “These are professions that you could be going into as well.”

Gina Stracuzzi: Sales can be so lucrative. If you are hitting your numbers and doing well, that gives you freedom to take off and go to a soccer game, because you don’t need to be in the office till 10:00 at night. There’s a lot of financial independence there and also opportunity for more flexibility, which is one of the reasons I love seeing women going into sales. There’s so many efforts underway now to recruit more and more women. I just had a conversation with somebody the other day who was talking about, we used to just go into colleges. Now we’re going into high schools and talking to them in ninth grade about the value of thinking about sales. I love what you’re doing at the grade school level. That is awesome.

Kristie Jones: The other thing that women have to do is they’re going to have to advocate for themselves. In some cases, I’ll be fairly blunt here, but I don’t know that all of the discrimination against women that’s going on is malicious. Some of it’s just ignorance. By not saying something, by being belittled or being dismissed in a meeting, and going back to your office and going on about your day and not taking somebody aside whose intentions were probably not to be harmful but were just unaware of that situation and the comments that were made. It was interesting. I was reading an article today from Harvard Business Review about the concept of blacklisting something and whitelisting something, and how there are underlying potential connotations there. I think, again, “chairman” of the board, not chair of the board. There’s a lot of things that are just embedded in our everyday vernacular that I think we could be more aware of.

I got a chance to go to the AA-ISP Leadership Conference in Chicago in person. It was amazing. One of the speakers there, her name’s Eva Helén, and she wrote a book called Women in Tech, a Book for Guys. She makes a very big distinction between being an advisor and being an advocate. I think a lot of men are being an advisor and providing advice, but there’s a difference between providing advice and actually advocating for someone. I think when a woman is in a business, she needs to understand that distinction well, and she needs to seek out not just advisors, but advocates. Because an advisor will give you advice, but an advocate will invite you to the board meeting.

Gina Stracuzzi: We talk about that a lot in the Women in Sales Leadership Forum, the difference between mentors and sponsors, but also having your allies. You are so right, Kristie, that often things that happen aren’t malicious. They’re just either how it’s always been done and nobody is correcting it, or people sometimes are just clueless. If you don’t speak up, nothing’s going to change. Speak up for other women. Take the person aside and say, “Hey, listen, I know you’re a good person. I just wonder if you realize what happened in there.” It doesn’t have to be adversarial. If they still do it after that, then you know you’ve got a different kind of problem. But usually people are like, “Oh my gosh, no, I didn’t mean that at all.” You just say it once and they’ll get it.

Kristie Jones: I think women also have to come to terms with the fact that we in some cases are our own worst enemy. I was talking to my son yesterday, he’s getting ready to graduate from college, and we’re starting to look at jobs together. We were on Indeed and we were on the campus recruiting website. A lot of the jobs, they needed two to four years’ of experience. He goes, “I don’t care.” He’s like, “What’s the worst that could happen? They never respond?” That’s a very male attitude. He’s like, “I got nothing to lose, I might as well do that.” But women will look that thing over and say, “Two to four years’ experience. Heck, I barely even had an internship in college,” and they won’t apply. I think there’s all this underlying psychology that nobody’s really talking about.

One of my favorite stories to tell was I went into a company when I first started my business in consulting to work with their sales team. Ironically, the top three sales reps were all women. I was doing a bunch of research on the prior year, and average sale, and close rate and all, I was getting all my sales data together. I about fell out of my chair when I realized that all three of those women in the prior year had been within $5,000 of each other at the end of the year. I walked into the male owner’s office and said, “Were you aware that all of these women are within $5,000 of each other?” He was like, “No.” I said, “That’s not a coincidence. That’s those women not wanting to outperform each other or make each other look bad.” They had a close relationship. It wasn’t conscious. I was convinced of that, but it was subconscious or unconscious.

I said to him, “As an experiment, I’m going to take one of these women and I’m going to work with her secretly on the side, and I’m going to pump her head full of positivity and I’m going to tell her she can do more. I’m going to challenge her to get a higher average sale.” A year later, she’d out-earned those other two by $100,000 in revenue.

I think we have to be conscious of the fact that sometimes we’re our own worst enemies. Sometimes we’re not comfortable competing, not just with men. We’re sometimes not comfortable competing with each other. I’d spent some time with all three of those ladies, all of which were in relationships, and said like, “How do you feel about out-earning your partner or your spouse?” Because that’s uncomfortable for some women.

I have a friend who runs a very successful business. She’s an S Corp. As a result, she pays herself a salary, but she pays herself a salary just under what her husband earns. I asked her why and she said, “I just don’t want him to feel emasculated. I want to make sure that he still feels like he’s the head of the household.” Those kind of things are prevalent. We spend a lot of time talking about how men are not helping us and that men are not supporting us or lifting us up. But in a lot of cases, like I said, 70 years ago, we were nurses, and secretaries, and teachers. Now, I don’t know that the psychology or the mentality has caught up with the fact that we’re in these positions.

Gina Stracuzzi: To your point earlier, it’s interesting because you have those situations where women don’t want to compete with one another. Then you have other situations, and this is more germane to corporate situations where there aren’t as many seats, or at least it’s not perceived that there are. It becomes more competitive than collaborative, and that doesn’t serve anyone either. Helping companies understand what’s happening, and as they open more doors, don’t make it competition for the women then. They should be able to stand on their own merits, and wherever they get to, they get to. But that doesn’t have to be at the expense of another woman who could be also in the top three.

It is interesting to really talk about the socialization of women and girls, and the role that plays. When women break out of that, especially in sales, it is the stratosphere, and it is wonderful. I haven’t heard too many stories about out-earning their spouse, but I suppose that is true. It wouldn’t surprise me, to be honest. Let’s talk a little bit about that, or a little bit about an adjacent issue, which is the lack of representation in female sales reps.

What do you think companies can do to attract more women and then retain them? Because that’s an issue that we’ve talked about quite a bit in the various women’s networking groups that I do, and on this podcast, and elsewhere, that sometimes women get into organizations and it is not what they expected, or there isn’t the support that they need in order to be successful. Some companies can attract them, but they can’t retain women. Do you find that within your sales company clients?

Kristie Jones: I haven’t found a ton of that, I’ll be honest. I think because just the world that I live in, we’re just so happy to have revenue we don’t care where it comes from, or who sells. [Laughs] But I do think of a couple of things. One, you have to be writing gender neutral job descriptions. There’s a website out there called, if you just Google gender neutral job description, it’ll come up. I run all of my job descriptions through there. It’ll flag. It’ll say, “These are masculine words. These are feminine words.” I keep rewriting my job description until I get to neutral. It is “crushing it,” “Rockstar,” those are very male dominant words. You’ve got to be very careful about the language that you use. Again, women won’t even apply if they don’t have the four years of experience you want. They’re sure as heck not going to apply if it sounds male-dominated. You’ve got to start by getting a gender neutral job description out there in the web.

I was on a panel at the AA-ISP Leadership Summit. Somebody stopped me afterwards and said, “No women are applying.” I go like, “Yeah, no women applied for me either.” He’s like, “Well, how are you hiring them?” I go, “You have to go find them.” You have to go find them in other sales arenas and convince them that it’s okay to come over to the tech side, the dark side. You can go there. There are loan officers at banks. They are in retail. There are a lot of places where women are dominant.

I grew up in a retail environment. I was a buyer with Macy’s. I had plenty of good female role models as leaders in the retail environment, but there were men at the top. They only went so far, but I was grateful to have worked for several female leaders in the stores and in the buying offices that really shaped me, and then I knew I had support from. But I’m in the same boat. I shared with you earlier that I spend about 20% of my time doing what I call hiring help for my clients, project managing the hiring process. Women aren’t applying for my jobs either. They have to go be found. You have to go out.

Even as a man or a woman, you have to build a female network who know other female sales reps. Again, we don’t have to take them from tech. There are plenty of industries where women are selling, and selling a different product or service, that could come into the SaaS world or could go into selling hospital equipment in healthcare. If you build it, they won’t come. You have to go get them.

Gina Stracuzzi: Well, what you said just made me think that the tendency is to send women to get women, but it might be of value to send men to get women. These are men that can have really frank and honest conversations with them about the environment that their company can offer them, and set them up with male allies in the company right from the start. Because that could really change the direction of male versus female, because it shouldn’t be that way.

There are lots of really wonderful men, and they make great allies. But they’re also fearful because they don’t want to be labeled as not helpful, or coming off as condescending or whatever it is. I’ve talked to a lot of men who are like, “I don’t want to be alone with a woman anymore in an office. I’m afraid I’m going to say the wrong things.” We have to get by that on both sides and open the communication up. But I think sending the right guys to do the recruiting could actually be pretty valuable.

Kristie Jones: I agree. Again, I have benefited from amazing male mentorship. Everything that started, as I mentioned, with my dad, and my brother who is an individual contributor, has also been very influential in how I’ve shaped things. But I have sought out both men and women. I by happenstance happened to move across the street from a very powerful female leader in St. Louis area, who is the CEO for the American Red Cross for the majority of Missouri and some of Arkansas. We spent our nights on my deck or her patio drinking wine and debriefing our day and talking about some of the challenges. Even though I was in a SaaS tech startup environment, she was running a nonprofit, there were so many lessons that we could share with each other. I was grateful to have her every day to be able to debrief with. That just fell into my lap. That was by the grace of God. But I’ve had to seek out other women.

I’ve run across other women that I have had to go back to and say, “Hey, I saw you speak at this conference. I want to spend some more time with you.” I totally agree that men could go in and will be helpful with the recruiting side, but I think this is kind of a own your own ship thing for women, where you’ve got to surround yourself with men or women that are going to help promote you, and support you, and make the introductions that you need to be made, and that will vote for you when it’s time for that promotion. You’ve got to be very discerning about who you bring into your circle to make sure that they’re going to be an advocate, not just someone who supports you.

Gina Stracuzzi: We like to leave our audiences with one piece of advice that they can put in place to improve or accelerate their sales career starting today. What advice would you have for women moving forward?

Kristie Jones: I think it’s kind of a culmination of everything we’ve said today. I think you need to be fearless in speaking up and saying things are not okay in a way that you can be heard. It’s not about stomping out or raising your voice. It’s about, “Hey, you’re probably not even aware that this happened in the meeting, or that you made this comment that made me feel small and invisible.” It’s our job. We are going to have to support each other. We’re also going to have to have uncomfortable conversations in order to help move it forward. No change in our country and other countries have happened without having uncomfortable conversations happen.

Transcribed by Mariana Badillo

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