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From 98% men to 55% women: 5 tips for gender diversity in tech sales

Rachel Bates knows a lot about diversity in tech sales – or lack thereof – in Boston’s thriving tech sector. Her wake-up moment was noticing a glaring lack of gender diversity in the tech industry when interviewing for new opportunities earlier in her career, in late 2016.

Keith MacKenzie
Keith MacKenzie

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“My experience up until that point in sales and in tech sales was that it’s been a heavy imbalance of males to females. When I was looking for a job, I had had interviews for sales leadership roles all around Boston and I counted that I actually met with 50 people, 49 of which were men.”

When 98% of the decision makers you come face to face with in the job hunt are men, that’s an embarrassingly telling statistic.

“I was amazed that it was so high,” says Rachel. “I started talking about it with people and I realized there was an appetite, especially after the [2016 American presidential] election, to talk about gender diversity in the workplace. People wanted to talk about why there was a lack of women in sales.”

Balancing act

Rachel’s experience is not just an anecdotal thing, nor is it an anomaly in the industry. In 2017, recruitment expert Carolyn Betts pointed out in Mashable that just 25% of salespeople in tech companies were women, and that number declines as you climb the ladder: just 12% of those in tech leadership roles were women.

That number calls for improvement, and there are reasons for the call: Microsoft’s Rakhi Voria writes in Forbes about the very tangible benefits of having women in sales, for instance, women are statistically better at sales than men are. She also points out that companies with a higher proportion of women in their employee base are more profitable, with that number even higher when companies have a higher number of female board directors.

More arguments for balance come forward: women are more collaborative and are excellent at building relationships; a crucial facet in sales where success comes out of building trust between parties. Rachel attests to this herself: “I’ve worked with many female sales executives, men too, who have different skills such as listening, [and] empathy that they can bring to the table, which is really important, particularly in inside sales.”

Plus, if the world out there is 50-50 in gender, that means your customer base is likely around that number as well. So, wouldn’t it make sense to build out a more gender-balanced tech sales team to best tap into the market?

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Seuss wisdom

There’s a moment in Dr. Seuss’ The Lorax where Ted, the main character, is given a seed by the Once-ler and is told: “I know it may seem small and insignificant, but it’s not about what it is, it’s about what it can become.” That seed of opportunity, for Rachel, came in the form of her long-time capacity as Workable’s Senior Vice President of Sales and Marketing.

“I started at Workable in November of 2016, and I was in a unique position in my career, because there was no sales team,” Rachel explains with a chuckle. “I was hired to build the sales team from scratch. I think there were two people in sales at the time, and then within the first couple of months, I realized we need to be at 50 by the end of 2017.”

That’s a significant task for a hiring manager; 50 hires in one year, or nearly one new salesperson per week. Rachel was upfront about the scale of that challenge, and realized this was her opportunity to lead the walk as well as talk the talk.

“I felt empowered, and this was the one time that I’m going to have a more gender-balanced team. It was my mission and it was really, really hard.”

Two years later, she points to her sales department and the presence of women is clear. As of December 2018, out of Workable’s approximately 65 employees across four different functions in sales, roughly 55% are women. Rachel considers this a significant accomplishment in her career, where she was able to step up and make a difference in her work environment and, she adds, cause ripples in Boston’s tech sector.

So, how did she do it? Rachel offers five tips for the budding tech sales diversifier:

1) Embrace the “nice to haves”

It’s easy to fall into the trap of hiring men to fill out your tech sales team because, for example, in Boston, the majority of those who meet your requirements of experience in tech sales are going to be men, says Rachel. After all, the disparity in gender is a self-perpetuating cycle – when tech sales is male-dominated, you’ll see more men than women applying for a job, which means more men being hired – by men – which means more experience on the resume for men than for women.

“If you put on your job description that you need two to three years of sales experience and you’re hiring in Boston, guess who you’re going to get?” Rachel says with a smile.

So, Rachel had to think about alternate ways to bring in female job seekers who could do the job. One way was to cast a wider net and consider those who have the skill sets you want to see in a salesperson but don’t necessarily have an expansive sales background. Rachel refers to Brooke Weimar, whom she hired in March 2017 to be an account executive. “[Brooke] lived in Alaska because of military history and had years of running a gym and hiring and running sales up there,” Rachel explains; “I was like, ‘Fantastic,’” and hired her for the position.

Brooke may not have possessed the traditional 2-3 years of software sales background that would be ideal, but the range of other sales skills in her resume was easily transferable in Rachel’s eyes. She’s now a senior global account executive at Workable.

Rachel emphasizes the value of assessing a candidate’s “other” skills and not being so quick to dismiss those without a comprehensive sales background.

“[You need to be] thinking about that on the job description: what’s required versus what’s nice to have. Then you might be open to more candidates.”

2) Broaden your announcements

Don’t just rely on the same sources for your candidates, Rachel stresses. There’s a danger in that, because many networks are limited to the same select few people with common links such as having attended the same university, worked together in a previous job, or are from the same area – which all lead you back to the same problem of lack of diversity in tech sales and, again, is a self-perpetuating thing. In a tech world where just 25% of the employee base consists of women, you’re going to find that same limitation in those professional networks.

“If you’re just using referrals, or perhaps only looking on LinkedIn for two to three years of experience, you’re only going to find the same type of candidates,” Rachel says. “Typically, I’ve found that women or even different types of people might not have access to the same networks that other people might.”

So, look outside of that traditional box. Broaden your horizons and look beyond the usual candidate resources by posting to specialized sites in addition to the popular ones, including those that cater to a specific niche such as She Geeks Out (SGO).

“[It’s] making sure that your job’s distributed and advertised in as many places,” Rachel says.

The result? More candidates to choose from.

“You are going to get a high volume of candidates. And there’s something to be said [for that]; once you have quantity, that you might get more at that level.”

3) Be loud, be proud

Don’t beat around the bush. Be overt and open about your initiative. Build active alliances with pro-diversity groups. Get involved in the conversation and insert yourself into it.

Rachel, for instance, participated regularly in events and podcasts hosted by SGO, outright promoting herself as an active proponent of gender diversity in tech sales.

“Be clear about what you’re doing and what you want to do with your tech sales team,” Rachel says of her experience working with SGO. “[This] developed a lot of internal conversations and I realized there was an appetite among the team that they wanted to talk about it, too.”

Rachel also established a reputation in Boston circles as someone who was not only passionate about gender diversity but was in a position to do something about it as well.

“And so,” she adds, “it became part of our conversation about ‘Why work at Workable?’ and ‘Why join the sales team?’, about the culture and the environment that we wanted to create.

“Recruiters started to talk into it, too. They said, ‘Rachel’s very passionate about it.’ And that made us more attractive to those female candidates who were applying.”

“Outright talking about the fact that you want to have a gender-balanced team is appealing in itself in developing relationships.” This can attract more female candidates to your team, too.

4) Build from the top-bottom

When you’re a female candidate looking for a job and you find that 49 of the 50 people who interviewed you are men, that signals a clear need for greater female representation in hiring teams in your industry. So, the fourth tip in Rachel’s arsenal is to ensure greater balance at that level and higher up.

“When [candidates] come in, make sure that they’re meeting with female leadership and they see people in these roles,” Rachel says, explaining that this wasn’t always the case in her career even when the team was clear about its priorities.

“I’d go in and we would hear about wanting to have a diverse sales team, and yet I’d only see males and I’d only meet with senior leadership who are men,” she says.

Having greater female representation at the start not only impacts your diversity initiative in a positive way, it also fosters greater inclusion.

“When they start, they feel more comfortable too, so it’s not just about your hiring process. It’s about the onboarding and making people feel welcome.”

If you don’t have female representation in your hiring teams or in the department, you can improvise: “If you don’t have them in the sales team, perhaps having some people from other teams for the inclusion aspect [will make a difference].”

In short: standing up and professing your support for diversity and inclusion is not enough. Take initiative and walk the walk in addition to talking the talk. Candidates will be more motivated to work for companies who represent and understand them, and back that up with action and culture.

5) Bolster the foundation

It’s not only about showing female leadership; you can also diversify your efforts at the entry-level positions and work your way up. Rachel refers to her own team as an example.

“Here, we have the SDR [sales development representative] team, which is more entry-level,” she explains. “We have people who come out typically from colleges, the recent graduates, or [those looking for a new career]. That’s a great place to start, because you’re not looking for experience, you’re looking for attitude, drive and other types of skills,” Rachel adds, alluding to her first tip of being open to those from different career backgrounds looking to move into sales and looking at the “nice to haves” in a resume.

Her efforts in doing so have benefited Workable as a whole. “I think we even have a higher proportion of SDRs who are now being promoted from within, so it’s building that long-term mix as well.”

Finding the balance

Rome wasn’t built in a day, and neither can diversity within your tech sales team. It’s a multi-pronged effort: cast a wider net by including more “nice to haves” in your job descriptions and advertising in more places, be clear and passionate about your initiative, bring in more women at the decision-making level, and build all of that up by filling entry-level positions with women.

But Rachel reminds us that once you take that step, you have to go all in to see those long-term benefits.

“Are you willing to wait another month because you want to interview three women before you hire the qualified men and make sure that they have criteria like that?” Rachel says. “You have to be prepared to put your business goals at risk to be able to do it ultimately. Which, I believe, will help your business succeed too.”

And the buy-in at the top level is essential. “You could do these five tactical things, but if you don’t have that executive leadership and want and drive to do it, it doesn’t make much of a difference,” says Rachel, noting that she had, and still has, the full support of Workable CEO Nikos Moraitakis – particularly when factoring in the impact to the bottom line of gender diversity in tech.

“It’s so much now that I think I have 60/40, and I need to recruit some more men,” Rachel laughs, before adding: “I think we’re just talking about having a more balanced workforce, right? So I think 50/50 is not a 60/40 or anything like that when we’re hiring at such a high volume; I don’t think it’s unreasonable. It’s bringing the needle closer to the middle.

“In building and growing our sales team I spend a lot of time thinking about balancing the types of people we have and might need on the team and the skill sets that they bring. I think when it’s 50/50, it’s not a minority. It’s like it’s a balance. It’s just about balancing it out.”

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