At first, Lori Richardson didn’t notice any difference between her experience in tech sales and the men on the team.

She started her career in the eighties, at a time when business and sales were booming. During her first job, she didn’t recall any issues of being passed over for roles or men on the team getting preferential treatment.

But then it came time to apply for her second job. As she watched men on her team leave for bigger opportunities and more pay, she had to fight through multiple, excruciating rounds of interviews for a higher role. Even when she earned the position, she felt like she had to win her employer over.

The reason: Most companies had never hired a woman in field sales (a senior position at the time), only support roles, Richardson said.

“Fortunately for me, I closed a multi-million dollar deal within 90 days,” Richardson said. “The [customer] worked with me because they didn’t like the guy who was the sales rep before me. … I salvaged that opportunity. That was a great turning point for me and gave me confidence.”

The erroneous assumption that women couldn’t excel in sales played a significant role in creating a gender disparity in sales leadership, according to a report from the Boston Consulting Group.

Biases like that have continued to manifest themselves in sales for decades. It’s there in the metaphors referencing sports dominated by men. It’s there in who has traditionally received promotions.

“In order for us to enact change in the future, we do need to have everyone there so that we can take forth these lessons and make progress.”

And it’s still there today in unequal pay and who does and doesn’t get brought into leadership meetings, Richardson said.

Some of these biases can be so subtle that it goes unnoticed on the sales floor unless it happens to you or you educate yourself about them. And yet, conversations from women about the bias they experience and how to fix it is often discussed in a room of just women, said Alexine Mudawar, a major account executive at Displayr.

“The demographic breakdown of [networking] groups lean predominantly men,” Mudawar said. “Within those groups, sometimes there is a smaller subset of women and I do feel like those conversations do end up getting siloed and we’re just talking amongst other women.”

The only way the industry is going to change is if everyone participates.

That’s something Richardson has been focused on changing throughout her career as a sales advisor and founder of WOMEN Sales Pros, a company dedicated to helping women advance in sales. It’s also part of the mission of the Women in Sales Club, a networking group launched by two Richardson mentees, Gong Sales Development Rep Manager Gabrielle Blackwell and Mudawar. (Richardson also serves as Women in Sales Club’s advisor).  

The group, which meets every Saturday on Clubhouse, is focused on enhancing and empowering women in sales, but they also want men involved in the conversation.

Since launching earlier this year, Women in Sales Club has gained more than 3,000 followers. They meet every Saturday and hold panel discussions on topics like ageism in sales, resilience and the power of finding community. Women and attendees from underrepresented communities in sales are front and center in the conversations, but they also want men in sales to show up, be vulnerable and listen.

“In order for us to enact change in the future, we do need to have everyone there so that we can take forth these lessons and make progress,” Mudawar said. “It is important for there to be representation from everyone in those discussions. And that was one piece I wasn’t necessarily seeing.”

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Participation Leads to Change

From the beginning, Blackwell and Mudawar wanted to reach a broader audience with their Women in Sales Club.

Both women knew what it felt like to be an “only” on the sales floor. Mudawar, who is now a major account executive at Displayr, started her career as the “only woman” on the sales floor; Blackwell, who is a sales development rep manager at Gong, began hers as the “only Black woman.” They also shared a passion for creating internal resource groups and training sessions to empower women on their teams and had participated in women networking rooms that were isolated to just women.

After meeting on the new social media app Clubhouse, they saw an opportunity to bring those conversations to a wider audience.

In the last few years, Richardson has seen an increase in women employee resource groups and networking groups within sales.

Women alone can’t carry the burden of change. Men still hold the majority of sales leadership positions at nearly 57 percent, according to research from the career website Zippia. As a result, the rooms where decisions on promotions, mentorship and project opportunities are made are often dominated by men.

“It’s critical for the success [of these initiatives]. I can’t just talk to a few people in the room and expect the world to change,” Richardson said. “Who are the leaders in companies? Well, they’re mostly white males right now. If that’s the case, we need to have those guys to be involved in what’s happening.”

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When men do take the time to engage in these conversations and educate themselves on the different experiences of women in sales, they can have a bigger impact as allies.

Richardson recalled an event she held in which women sales reps shared their fears that they wouldn’t be able to have children and still work in sales. Their reason: The time off would be too difficult to come back from, Richardson said.

That insight shocked one of the men in the room. He went back to his own company and created a sales-specific parental leave policy designed to alleviate those concerns, Richardson said.

“People aren’t thinking about those things because they don’t have relationships with anyone that has [a different] experience.”

That can be the impact, but it’s just one small instance. Too often, Richardson has privately given feedback to men in leadership roles about how they can better support women and they respond defensively.

“All I want is for men to be open and to not be defensive,” Richardson said.

Mudawar has received messages from chief revenue officers and sales leaders who are men asking what they can do to recruit and retain more women sales reps. If more men in leadership attended meetings like Women in Sales Club, they’d become more aware of any activity that could be driving women out of sales, Blackwell said. 

They might learn that their use of “bro” or promotion decisions are actually creating a culture that’s driving away women, Blackwell added.

“People aren’t thinking about those things because they don’t have relationships with anyone that has [a different] experience,” Blackwell said. “It doesn’t mean you’re a terrible human being or company, but it could be experienced as inconsiderate and not thoughtful, which is the antithesis of what you want to do with diversity and inclusion.”

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One of the most important steps men can take to be better allies to women in sales is to take the stories and lessons they learn from the club and educate their teams, Blackwell said. Speaking up is the fastest way to turn DEI from lip service to action.

“The takeaway [for men] is not just ‘I can mentor other people,’ but I can bring the learnings from what’s happening in the Women In Sales Club into these rooms where decisions are being made and have a big impact,” Blackwell said.

Mudawar also wants to see more men step in to mentor and sponsor other women. Mentorship and sponsorship, which involves a senior-level employee advocating for a colleague, are both essential to career growth. A study from diversity nonprofit Catalyst found that having a mentor and sponsor can be a differentiating factor for who gets leadership roles and are crucial to helping women overcome barriers that typically stand in the way of career progression.

“Find some women on your team and switch things up so you can learn from their experiences and what their experience working in their organization has been, and help coach them as well.”

Yet, 36 percent of men who are managers were hesitant to mentor and work one-to-one with women because they were “nervous for how it would look,” according to a study from Lean In, an organization focused on helping women advance in the workplace.

While women sales reps often get paired with women managers, that’s not always an opportunity for many women in sales as men remain the majority of leaders. If men don’t step up to mentor other women, then those opportunities for career advancement will continue to be lost.

“Find some women on your team and switch things up so you can learn from their experiences and what their experience working in their organization has been, and help coach them as well,” Mudawar said.

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Show Up, Be Vulnerable

Before Mudawar and Blackwell start a Women in Sales Club session, they reestablish the group’s intentions.

First, they explain that it is a club for women, but they also take care to point out that men will also be in the room. Overcommunicating the purpose of the room and the desire to connect with all attendees creates a more inclusive environment that allows everyone to be vulnerable, Blackwell said.

“Without having those integrated conversations, people are just going to be resentful,” Blackwell said. “I don’t think you can actually have an inclusive environment, you can’t foster a culture of diversity and equity in a place where everybody is afraid of irritating each other.”

The most important thing a man looking to be an ally can do in spaces like Women in Sales Club is to be vulnerable and show up ready to learn, Mudawar and Blackwell explained. For their part as the leads of the room, they encourage all attendees to ask difficult questions. As long as the person comes from a place of learning, they’ll assume positive intent. When a man takes the time to ask questions during a meeting, that’s often where learning happens.

“Without having those integrated conversations, people are just going to be resentful.”

“We’ve had situations where men in the group say, ‘Wow, I’m listening to these stories and it’s hard to hear these experiences. What can I do?’” Mudawar said. “That person is showing up multiple Saturdays trying to do better. … So, we’re like, ‘Here are some things to think about and look out for these situations in the future.’ That in itself is a step.” 

But the room isn’t there to pander to men and fix everything. The intent is for men to engage in the conversation. Otherwise, nobody wins, Blackwell said.

“You have to have men in the room raise their hand and go, ‘What can I do better? What can I do to support?’” Blackwell said. “That’s what we want. We want men to feel as though the door is open for them to engage.”

As Women in Sales Club grows, Mudawar and Blackwell’s goal isn’t for it to be a space that’s just for women. Instead, their hope is that the community will look like the future of sales.

“I think about the rooms we host and the people who show up, and that’s what I want the future of sales teams to look like,” Mudawar said. “We have folks who are diverse in every single aspect from age to race to educational background to work history. In the future, we hope to see a [sales] team that looks like who is coming to these conversations.”

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Still, sales has a long way to go to be diverse and inclusive. While Richardson has seen more diversity and inclusion initiatives within the profession, the pandemic also created setbacks for women. More women left their sales jobs, went part-time or were laid off than men, Richardson said.

Richardson does remain hopeful that the remote environment and the deemphasis on travel for senior sales roles will mean more opportunities for women to advance their careers. However, change will hinge on whether sales leaders are simply paying lip service to DEI or participating in the conversation.

“I’ve seen companies that have improved their policies because the employee can go wherever they want now,” Richardson said. “Women that I know didn’t feel listened to, who were frustrated at their companies, they’re going to leave. Or their companies are going to start to listen and make changes so that they feel valued.”

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