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Lori Richardson’s 40-plus-year career has been defined by her support of fellow women in sales.
Since 2015, Richardson has worked with Women Sales Pros, an organization that strives to recruit and retain female talent in the sales world. Through her work with the organization, she wrote the 2023 book She Sells: Attract, Promote, and Retain Great Women in B2B Sales and has been hosting the Conversations with Women in Sales podcast since 2020, spotlighting “a woman in sales who is doing incredible work” every week, according to its bio.
Richardson spoke with Revenue Brew about her mentorship, how to overcome generational stigmas, and the future of women in sales.
This conversation has been edited and condensed for clarity.
How did you get started in sales?
I loved school so much, but when I got to high school, I didn’t like it at all. It was very cliquey. I was working in middle school—I’d go to my grandmother’s after school, so it kept me busy, but in high school, I just didn’t like it… When I heard that you could take a GED test and get out of high school I thought, “Well, why would I want to be here, if that was the case?” I didn’t study; I went to a location; I took the test and passed.
At 16, I left, and I got into college and I got my degree in early childhood education. I got a two year degree. I was doing great. I was on the fast track, and then I got pregnant, and then I got married, and I married an abusive person, so I left for my life. At 19 years old, here I was with a baby, and I’m working in teaching, which didn’t pay me enough to support my family, so I thought maybe I could sell something. Technology was really taking off back then—this was the early ’80s—and I thought, maybe I could sell something in technology.
How did you work up the ranks in the sales world?
I grew up in Seattle, so that was when Bill Gates was starting Microsoft and he wanted to put a computer on everybody’s desk. I thought, “I could sell a lot of those.” I got a job selling technology—selling computers, peripherals, and software. We sold software in a box back then, and I got a job in it, and it was amazing. I went from one company to a better organization, and then I was calling on big corporations and working with Boeing and all sorts of different companies, selling them hundreds of thousands of dollars worth of products. Sales enabled me to be able to leave work and take care of my family.
How did you get started with Women Sales Pros?
Initially, it was a group of 50 women sales experts like myself. We had our own companies. It was started by a woman named Jill Konrath, who was one of my mentors. She’s written a number of books on sales. She was the big deal back then on the main stages. She would be the one woman with all the other men on the stage. At some point, I expanded that from helping this small group of 50 women. I wanted to help women in sales in general, so I did some virtual events. Then I realized during the pandemic, there were more women in sales groups sprouting up, and I didn’t want to compete with them. People would say, “I don’t know if I should sponsor your group or this other group,” and I said, “No, you sponsor anybody you want. We’re all working toward the same thing. We want more women in sales.” Now I work as a megaphone. I’m a pipeline. I support all the different women in sales groups.
What kind of work do you do with the organization?
Where I think we miss a mark sometimes as women is that we go off, we start something and kind of do it on our own, but we don’t get all these other people involved. I’m bringing them in—all the other women in sales groups—so that we can affect change to help. There’s still women that are paid less than men in some sales and sales leadership roles. Clearly, men are promoted more than women, so I’m working to help women know what to do to go to the next level in their organization. A lot of women just get tired of being around this male-majority world, and they go off. We see more women leaving in their 30s and 40s now than we ever did to launch their own business where they might consult or be a fractional chief revenue officer or a fractional sales leader.
How are you helping women find success in sales?
The first thing is mindset. I speak a lot about mindset. We speak about not waiting for someone to tap you on the shoulder for a promotion. You should be clear. I should go to you and say, “I want your job.” If you’re my boss, tell me how to get there because men are very comfortable doing that. As women, we were not raised to do that typically—don’t make waves, don’t speak up, just kind of go with the flow. Now, we’re seeing more women that are able to speak up and say, “I want to negotiate my salary.” I’ve had situations where a leader told me she interviewed seven people for managers: four were men, three were women. Every one of the men asked to negotiate their salary, and none of the women did, so it’s helping to break these societal norms.
How do you see generational stigmas still impacting women in sales?
There are over 200 schools around the country that have sales programs, and women excel in them. Sometimes professors that I know will hyperlink me on LinkedIn when they show this picture of five women who are all the finalists, because they have competitions around the country. We take these very successful women, and they get an entry-level job in sales. Then they might get a sales manager position as equally as the men. But, then the men get the next promotions more than women do. They call it “the missing rung.” Women just get stuck there and more men will go on. Then they, of course, will get higher salaries, and, of course, they’ll get promoted, and then they’re in the C-suite eventually. What I say is, “How do we have all these amazing women in university sales programs? How come 50% of sales leaders are not women?” That’s what I’m very curious about, and it’s because of the system.
What can sales organizations and sales leaders do to make their teams more inclusive?
Many people seem to understand that teams, in general, are more profitable when they’re more inclusive, but they don’t seem to put it into action. I would say it’s really to take action, to look in different places on where to hire. Look at different ways, don’t just do the same things that you’ve done over and over again, which is typically what we do in sales. Sales often will promote the top salesperson into management because there’s so many systemic things.
I'll give you an example. People will say, “Who are the top sales leaders on LinkedIn? Let’s do a poll and see.” They’ll get the names of almost all men because more men are on LinkedIn than women. Many women look at LinkedIn, but they don’t comment. Isn’t that interesting? They’ll come up with their list, and there’s 100 men. When you think about it, it makes sense, but it’s harder to be like, “I wonder who’s not on here that should [be]. How could we be a little more diverse in our thinking?”
In a time where people in government are saying this is not a good thing, I’m going to keep pushing for it because we know it builds better teams, and we know it builds better business.