Helen Lee Kupp helped scale Slack from $75M to $1B. Now she is on a mission to close the AI gender gap

Helen Lee Kupp studied chemical engineering at Caltech and started her career at Bain & Company before moving into the Bay Area startup ecosystem. She joined Slack as the company’s strategy and analytics lead, shepherding it from $75 million in annual recurring revenue to more than $1 billion in enterprise ARR. She launched the enterprise product, led the push into international markets, and then co-founded Future Forum, a future-of-work research consortium backed by Slack and Salesforce. Along the way, she co-authored the Wall Street Journal bestseller How The Future Works.

Her career, in other words, was built on the operator side of technology: growth, product, systems. “I was working in AI before AI became the centre of the world’s attention,” she says. “It was just one part of the broader technology landscape.”

Then she became a mother. And then a mother again. And again. Life, as it does for many women in high-intensity careers, imposed its own set of priorities. She stepped back from the most demanding day-to-day startup work. It was not a retreat. It was the kind of recalibration that millions of women make and that the professional world rarely knows how to value.

When generative AI began to accelerate about three years ago, Kupp felt pulled back in. “It felt like one of those moments where you could see a major shift happening in real time,” she says. “I knew I did not want to only watch from the sidelines. I wanted to engage with it directly.”

What can I build right now?

Her first instinct was to start her own company. She did a co-founder search and explored the conventional routes, but ran into realities women in technology know well: the venture funding gap, the scepticism directed at solo female founders, the distance between the official language of inclusion and the actual behaviour of the market. “I have a lot of feelings about that,” she says, “because the official explanations and the actual behaviour often do not match.”

She could have spent years pushing against that system. But Kupp has never been especially interested in waiting for permission. “At some point I realised that trying to change that system head-on was going to be painfully slow,” she says. “So instead of asking, how do I force the system to become fair overnight, I started asking, what can I build right now that would help the women around me?”

That question became Women Defining AI. It was not supposed to be an organisation. It was supposed to be a small study group where Kupp could share what she was learning. She expected perhaps five women to join. Within days, 50 had signed up. Within a couple of months, 150. “That was the moment when it became clear that there was a need here much larger than I had anticipated,” she says.

The demand revealed something deeper than a skills gap. “A lot of women were looking at AI and feeling that they were already late, or that they were underqualified, or that this space belonged to someone else,” Kupp says. “That matters because once people internalise that they are outsiders to a shift, they start opting out before they even begin.”

“Women did not just want information,” she says. “They wanted a space where experimentation felt possible, where questions were welcome, and where they could be surrounded by people who were not making them feel perpetually one step behind.” Over time, the study group formalised. Kupp began running events, workshops, and structured programming. Eventually she turned it into a nonprofit, because by then it was clear that this was not a temporary conversation.

Women have always been builders

This is where Kupp’s argument becomes most forceful. She believes the technology world has narrowed the definition of “building” to the point where most women cannot see themselves in it. “A builder is seen as someone who writes code, raises capital, creates a platform, launches a product, and scales a company,” she says. “That is one valid form of building. Of course it is. But it is not the only one.”

Women, she argues, have long been creators of systems and solutions. Much of that work has simply not been described in the same prestigious language. “It has been described as care work, coordination, emotional labour, teaching, or simply helping,” she says. “In reality, a lot of that is systems design. A lot of that is invention under pressure.”

When women say they are not technical enough to build, Kupp hears something different. “What I often hear is: I have been taught not to recognise my own forms of building as legitimate,” she says. AI creates an opening, she argues, because building increasingly begins with language, judgment, and problem definition. “If you are a strong writer, a strong thinker, a strong operator, you already hold some of the ingredients,” she says. “The question is whether the culture around you allows you to see that.”

Her conclusion is blunt. “If we want more women in AI, I do not think it is enough to simply invite them into the old story,” she says. “I think we need to rewrite the story itself.”

Beyond the ritual of diagnosis

Kupp is impatient with the way the conversation about women in technology tends to cycle. The statistics get repeated. The inequality gets diagnosed. Then everybody nods and moves on. “The discussion too often stops at the level of grievance or diagnosis,” she says. “It becomes a recurring ritual. And rituals can become strangely comfortable even when they are describing something unjust.”

She is not naive about structural inequality. Venture capital is still venture capital. Bias is still real. But she is wary of a narrative that defines women solely through their exclusion. “There is danger in allowing the story to become purely one of victimhood, because then people internalise helplessness,” she says. “And helplessness is exactly what the system benefits from.” What she wants instead is honesty about the barriers, paired with structures that help women act despite them. “That is a different energy,” she says. “It is more generative, and frankly more useful.”

The window that will not stay open

Kupp’s deeper worry is time. AI is still visible enough that people are questioning it, noticing biases, debating guardrails. But that scrutiny will not last. “As AI gets embedded into products, software layers, internal tools, and workflows, it will start to disappear from view,” she says. “It will become background infrastructure. Most people will stop asking what it is doing underneath. Women need to be in that conversation now, while the assumptions are still contestable.”

She frames reskilling not as a training course but as a shift in identity. “If a woman has spent years in a role now considered vulnerable to automation, the question should not just be how do we train her to survive,” she says. “It should be how do we help her understand that her knowledge is valuable raw material for creating the next solution.”

She points to her own experiment building a chief-of-staff system this year, a role that sits between operations, executive support, coordination, and communication, the kind of work many women have done for years. Kupp’s response to the possibility that such roles might be automated was to build the tool herself. “If I understand what makes a great chief of staff, why should someone else build that first?” she says. “The domain expert can become the builder.”

The question that interests her most

The mission of Women Defining AI is to get more women and non-binary leaders from zero to building. But the deeper issue, Kupp says, is power. “Who gets to define the tools?” she asks. “Who gets to shape the assumptions inside the systems that increasingly organise work and life?”

“If women continue to see themselves as outside that process, they remain downstream from decisions made by others,” she says. “But if they see themselves as builders, they begin to move upstream. They start to define, not just adapt.”

When asked for the biggest misconception she wants to challenge, her answer comes quickly. “Women often have extraordinary expertise, excellent judgement, and domain knowledge that the tech world routinely overlooks,” she says. “What they often lack is not capability. It is reinforcement. It is access. It is community.”

“Once women start identifying as builders, the whole conversation changes,” she says. “It moves from asking why women are excluded to asking what happens when women fully participate in shaping the future.”

Helen Lee Kupp did not wait for the system to invite her. She started with a study group for five. It became a movement of hundreds. And the question she keeps returning to is not whether women belong in AI. It is what they will build once they stop doubting that they do.