Inside Writer

– 12 min read

Women in sales at Writer

Taking the lead in enterprise AI

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Writer Team   |  March 7, 2025

Women in sales at Writer: Taking the lead in enterprise AI

In honor of International Women’s Day, we’re spotlighting the incredible women in sales roles who drive AI adoption among enterprises. Despite the industry’s low levels of representation and barriers to career progress, they’re climbing the ladder and leading transformative change.

To truly accelerate action for gender equality, companies must prioritize and actively support women. At Writer, we believe that women in tech sales shouldn’t fight to make their voices heard — they should actively lead their field. And it’s our responsibility to uplift their voices. With a women-forward team and a female CEO, May Habib, at the helm, we’re creating an environment where women confidently thrive and lead.

Meet a few of the talented women at Writer who set the standard for excellence in sales:

  • Alice Chang, head of SDR and PLG
  • Jess Tourville, enterprise account executive
  • Nicole Morris, enterprise account executive
  • Kayla Jacobs, account executive

Summarized by Writer

  • Women at Writer, including our female CEO, are leading the charge in AI adoption, despite the tech industry’s low levels of female representation.
  • The company’s sales leaders, such as Alice Chang, Jess Tourville, Nicole Morris, and Kayla Jacobs, highlight the importance of representation and the unique skills women bring to AI sales.
  • The presence of a female CEO like May Habib provides a powerful role model, fostering an environment where women can thrive and lead with confidence.
  • The company’s core values of connect, challenge encourage a human-centric workforce, making Writer an Inc. 2024 best workplace and a top choice for women in AI sales.

The challenges of working in a male-dominated industry

Innovation and disruption are the norm in the tech industry, but one thing remains stubbornly unchanged: the gender gap. As of 2022, women make up only 28% of the tech industry workforce. Women fill just 37% of entry-level roles, setting the stage for a cascading effect throughout their careers. By the time they reach the senior VP level, this number plummets to a mere 19%. This “broken rung” phenomenon makes it difficult for women to climb the corporate ladder and severely limits the visibility of female role models at the top.

Being the only woman in the room

With such low representation, it’s not uncommon for women in tech sales to find themselves as the only woman in the room. Jess Tourville says she can count on one, maybe two hands, the close female colleagues she’s had working in tech sales for 12 plus years. This can be isolating and intimidating, but it also presents an opportunity for resilience and leadership.

Nicole Morris realized early in her career she was often the only woman in the room, which came with the pressure to prove herself and justify her expertise more than others.

“Instead of letting that discourage me, I try to see it as an opportunity to lead by example and show that women really do belong at every single table — not just as contributors, but as decision-makers, as thought partners, and really as innovators,” Morris says. “And in AI in particular, the challenge is even more pronounced because the space is really marked by very high expectations, but also a lot of noise, and everybody is expecting generative AI to be the next big thing, but most companies are really floundering as a lot of folks are over-promising and under-delivering.”

The higher up the ladder you go, the less representation you encounter. This lack of female leadership makes navigating and advancing in the industry even more challenging.

Lacking representation and role models

Even at the beginning of the pipeline, women are less likely than men to get hired for entry-level roles. Men significantly outnumber women at the manager level, making it incredibly difficult for companies to support sustained progress at more senior levels. According to the World Economic Forum’s Global Gender Gap Report 2024, it’ll take until 2158 to reach full gender parity.

“Specifically for sales — and I will say enterprise sales — [when you look at] the presence of female leadership, the air gets thinner at the top,” Alice Chang says.

This lack of visibility has far-reaching implications, affecting how companies identify and nurture talent. When most leaders are men, the criteria for success and the attributes of a successful candidate can become skewed.

“Representation cascades down to ‘How do we pattern recognize successful attributes?’ And when you have a diverse sort of representation in more senior leadership positions, the way each of them identifies talent, objectively, what seems to be a successful candidate, how we hire, how we interview, and then the future talent pipeline, then it gets kind of pulled into the company,” Chang says. “It makes a huge impact for like different layers in the company hierarchy.”

For Kayla Jacobs, the presence of Habib as CEO was a decisive factor in her decision to join Writer.

“You always want to have someone that you can look up to that’s doing the thing that you ultimately want to do or showing that leadership that you’re trying to evolve into,” Jacobs says. “So having May be here was a really big factor for me in actually coming to Writer.”

Breaking new ground — and glass ceilings — in AI

If we want to reach gender parity before five generations pass us by, AI offers a promising solution. Many of the early use cases for AI were in functions like marketing or customer support — sectors that women have historically dominated. In the US, nearly 70% of customer service representatives and almost 60% of marketers identify as women. This is a chance to develop the workplace skills of the future before — or at least in pace with — our male counterparts.

“What I’m seeing in AI is it can be used in any department, especially Writer,” Tourville says. “So at Writer, our buyer profile is everyone under the sun in theory, right? So what I’m really enjoying about that is when I think about some of these accounts that I’m working with and some of the really close relationships I’m building, it’s all with very successful women within these organizations.”

At Davos, Habib highlighted the significant role women are playing in AI. Two-thirds of our top customers have women as executive buyers, champions, or both — nearly a quarter falling into both categories.

When you look at generative AI adoption by seniority and function at tech companies, women are actually leading the way. Senior women in technical functions — engineering, IT, customer support, sales, and marketing — are ahead of their men counterparts in adopting generative AI.

“I actually think with the introduction of AI, [it] requires somebody who is analytical, strategic, and can pattern match the nuances and deep understanding of a workflow or how work is being done, and apply this technology in a really seamless way, woven into the fabric of people, how they do work,” Chang says. “How do you do that? Well, you really have to have active listening, and the ability to observe and be very open-minded and low ego on where this path would take you. And I tend to find that a lot of female candidates really do that well.”

Women taking the lead at Writer

67% of US-based women C-suite officers, executives, and mid-level managers still say there aren’t enough women leading the conversation about generative AI. At Writer, this is where we want to lead by example. We’ve built a women-forward team backed and advised by successful women, leading to measurable success. Companies with more than 30% women executives are more likely to outperform companies with 10% to 30% women executives. And these companies are more likely to outperform those with even fewer women executives, or none at all.

The power of having a woman founder and CEO

Women represent fewer than 20% of leadership positions in the tech industry, with a mere 15% holding the title of CEO. Talented women don’t just lead Writer, the company is founded by one. Our co-founder and CEO May Habib is one of only 12 women co-founders and five women CEOs on the Forbes’ AI 50 list.

Tourville says that the diversity she sees at Writer is unlike anything she has experienced before, and she believes it starts from the top.

“Anyone that knows Writer knows May, and it’s amazing to see, and it’s such an inspiration. I think everything starts at the top,” Tourville says. “So I think having a female CEO, that trickles down into all the different departments.”

For Jacobs, one of her favorite things about working at Writer is having Habib at the helm. The presence of a strong female CEO not only provides a powerful role model but also fosters an environment where women can thrive and reach their full potential.

“I have a direct manager who is a female. I see other managers in leadership in sales that are female. I have a VP that is a female. We have enterprise sales leaders that are females,” Jacobs says. “We also have a ton of enterprise sellers that are females, but this also goes across the board…There are so many women that I can look to, to ask for advice, to ask for mentorship, to be able to follow in their example, and follow in their footsteps here of the paths that they’ve taken.”

As the Head of SDR and PLG at Writer, Chang has undergone significant growth and learning under Habib’s leadership.

“You really have a role model, and it gives you permission to express yourself in a different way, seeing that there’s a female leader who has succeeded and carved out a space for herself in these very crowded rooms,” Chang says. “And for me, as a female sales leader, I have learned and benefited from this representation of female leadership.”

Connecting, challenging, and owning at Writer

Our three core values at Writer are connect, challenge, and own. We approach hiring with purpose — seeking not just employees — but true team players eager to invest their passion and skills.

This emphasis on culture and a human-centric workforce landed us on Inc.’s 2024 best workplaces list. We’ve also been listed in Business Insider’s startups to bet your career on.

“I think with this connect, challenge, own that we’re bringing to the fold, it’s really encouraging anyone — especially women — to be able to speak up and voice their opinion and challenge when they feel that they have something really important to say and really wanting to stand behind their beliefs for something that’s going on with the customer or for anything that you’re doing,” Jacobs says.

And for Morris, she says that “own” is where she’s seen the biggest difference compared to other companies. Writer doesn’t view ownership as a buzzword but as a way of working and an expectation.

“I’m trusted to lead, to execute, and really to drive outcomes without micromanagement, and that level of autonomy is really empowering, especially as a woman in sales, because it reinforces my expertise and my judgment,” Morris says. “At many companies, these values are like words that are written on a wall, but they’re not lived day-to-day. And again, at Writer, it’s not just part of the culture. It defines the culture. And that makes all of the difference in creating an environment where I, as a woman, can thrive and lead with confidence.”

Our advice for saleswomen in generative AI

When we look specifically at sales, women represent only 40% of mid-level B2B sales employees, dropping to 31% at the senior level. Now is the time to increase those numbers, and AI gives us the perfect opportunity. So, if you’re a woman interested in a sales career in generative AI, this is what our leading women at Writer have to say.

“Here is the thing that I’ve learned firsthand from May Habib. When you walk in and you clearly know the market, you know their industry, you know their customers, you know your product and your value proposition better than anybody else, you really shift the conversation,” Morris explains. “And suddenly, it’s not about gender, it’s about expertise. It’s really been confidence-building to be at Writer at a place where we don’t just make claims, but we actually deliver results. We’ve helped more enterprises build and scale ROI-positive AI programs than anybody else. And so that has been really inspiring.”

We work with hundreds of enterprises like Accenture, Intuit, L’Oréal, Uber, and Vanguard to transform the way they work by automating their mission-critical workflows.

“It’s a really fun space to be in if you’re ready to work hard,” Tourville says. “You have to be on your toes 24/7, but get to be along for some transformational journeys with large, well-known customers. This is an incredible opportunity to get in front of some of the very biggest of the big companies with the biggest household names you’ve ever seen because they are starting their journeys [in AI].”

Take the lead at Writer

Here at Writer, we’re committed to accelerating action for gender equality. If you’re a woman in tech sales looking for a supportive and inclusive environment, Writer is the place for you.

Check out our careers page and be part of a community that values and empowers women to lead and succeed.