A potent combination of sales skills and AI technology may prove to be a boost to women seeking leadership roles in today’s organizations. But the path to success requires greater amounts of education and and a sense of curiosity.

That’s the view of Cherilynn Castleman , managing partner at CGI LLC, Harvard instructor, and co-chair of the Women in Revenue AI Leadership Council, along with Dr. Ginna Santy , executive director of Women in Revenue . I recently had the opportunity to meet with Castleman and Santy, who discussed the challenges ahead.

Overall, progress has been slow, with the share of women in leadership positions declining in recent years. Liz Elting, in a recent Forbes article , cites data from Grant Thornton that shows women currently hold just 31% of senior leadership roles in the U.S., down from 34% in 2025 and 35% in 2024. Internationally, women make up 28% of leadership positions, according to a report out of the World Economic Forum.

Overall, women represent just over half of the overall workforce, according to data from the U.S. Bureau of Labor Statistics.

Now, a combination of sales skills and AI may help change this equation. “Sales is a gateway skill, which opens doors because one needs to convince about their ideas and thoughts to get promoted and hired,” said Castleman. “Sales as a gateway skill and AI as a gateway technology, put together, is the fastest path to get in the room where decisions are made. Master sales skills and AI technology, and your doors are open."

It’s all about gaining AI fluency from the point of ideation and development, Castleman urged. “Women are heaviest users of AI tools anywhere, but we’re rarely in the room when the tools are designed. Women need to be coached and trained ”to be excellent at these systems that nobody asked us how to build, how to help build, and none of us were in the room when those were designed.”

AI also serves as a valuable tool to provide financial fluency. The ability to track and increase revenues is the most prominent skill organizations seek in leaders. “You have to demonstrate value financially,” said Santy. "You have to bring the judgment, but if you didn’t take finance or accounting, AI will do that heavy lifting for you.”

Learning to navigate the so-called attention economy is another key skill. “We’re drowning in noise all the time,” said Santy. “To be able to curate your way through it and stand out in it in some way is becoming exponentially more difficult as AI produces more and more content.”

It’s pertinent to develop the skills to navigate a world in which transactions are conducted by bots and systems more than humans. “How do we stand out in that world,” Santy asked. “That is part and parcel to sales, and something I hope women in particular really pay some considerable attention to.”

While AI and technology handles data and pattern recognition with ease, business is still person to person, said Castleman. “What sells is people knowing that you care about them.”

Even in a world dominated by agents selling to agents, “decisions still come down to a relationship between a salesperson and a buyer, and that will never change,” said Castleman. “Every salesperson will have agents that they’ll be working with, but ultimately, in the end, the relationship is built on trust – the trust, the caring, the relationship, understanding, and the judgment. The most successful people are the ones that get sit between technology and the buyer with their judgment – that will become a super skill.”

Castleman and Santy were motivated to create their group’s AI Council as they were seeing “the same old narratives playing out” as with previous technologies. “For all the talk of AI being a great disruptor or revolutionary moment, ”it sure seems like it’s just the same old, same old – with women being disproportionately replaced in jobs, and the victims of bias, without the access to jobs in AI that there are for men," said Santy. “We decided it is way too early to write the ending of this story. We’re focused on getting women in the room.

AI may serve as a great equalizer when it comes to business advancement, they believe. “It doesn’t replace what a woman knows. It amplifies her skills, her judgment, and it makes it more impossible for her to be overlooked,” said Castleman. "We are not going to be behind, we’re going to be elevated and amplified."

To help move forward, Santy urges “interfering,” proactively interjecting themselves into the AI decision-making process. “We’re not waiting for anyone to invite us,” she said.

Entrepreneurship is another path for advancement. “There are more solopreneur millionaires now because of AI than there have ever been,” Castleman said. “The cool part is women have a choice,” Santy added. “They can become entrepreneurs, and AI is their great thinking partner. And it can help them amplify their skills and become better leaders."

Another quality that needs to be brought out is a sense of curiosity. “It takes courage to be curious,” said Santy. “We throw the term curiosity around a lot, but it does take courage, because it means rejecting what has come before and being able to envision something entirely new."

Along with courage, sales skills are crucial in today’s AI-driven economy. “Sales is about listening, about caring, it’s the soft skills," said Castleman.