Context about Our Thesis & Recommendations
Prior Bias Should Not Constrict Our Future
At WiLAI, we believe that surfacing and discussing these biases, providing guidance and solutions, and spotlighting women's expertise and leadership will result in greater gender parity at all levels in legal AI.
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We need new solutions, for a very old problem . . .
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1800s
Prior Biases
Prior Biases Should Not Shape Our Future
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Visit our Statistics pages, and you will see bias across all areas of AI, including legal AI. It is happening in law firms, in corporate law departments, and in investment decisions. Perhaps unintentionally, venture capital and private equity investments are significantly predisposed against women, and the numbers are getting worse. In 2023, women founders received less than 3% of VC funding (around 2.3% for all-women teams), even though nearly 40% of startups are founded by women. In 2025 and 2026, the number dropped further: only 1.1% of women funders received VC funding.
Several studies (which you can find in the Research Knowledge Hub of our WiLAI News site) have identified many of the causes, including: investor stereotypes, different pitch evaluations, lack of women's access to (and comfort in) male-dominated networks, and pattern-matching to past successes -- all of which unfairly disadvantage women with qualifications similar to or even better than those of their male peers.
These systemic issues mean that women face harsher scrutiny and lower funding amounts and opportunities, despite research suggesting that women-led companies can outperform others.
1900s
Key Manifestations
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Funding Gap: All-female founding teams get only ~2% of all VC dollars, and companies with any women on the founding team get less than 15%. All-male founding teams receive the remaining 83% of all VC funding.
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Pitch Evaluation: VCs ask men positive "promotion" questions (how they will grow), while women are asked negative "prevention" questions (how they will avoid loss), favoring men.
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Network Disparity: Women have less access to crucial VC networks and often struggle to break into the male-dominated "boys' club". A sense of exclusion or discomfort in deeply male network is one of the deepest hindrances to gender parity in investing and hiring.
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Stereotypes & Perception: Investors perceive women as riskier or less suitable for high-growth ventures, even when their track records are similar to men's.
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Voice & Language Bias: Identical pitches are rated better when narrated by a male voice; VCs use more leader-like language when describing men and their pitch teams.
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Post-Failure Impact: A past failure hurts women's future funding prospects much more than men's, according to NBER research.
2026
Why Does It Still Persist?
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Chain of Command: Because the vast majority of current leaders in AI (including legal AI) are men, when they choose colleagues for leadership, speaking engagements, key assignments, and for other important positions and opportunities, they look to their left and right and think there are only other men as choices. These habits start at the very top of the chain of command and are perpetuated throughout their existing set of (mostly, or all) male colleagues.
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Lack of Funder Diversity: The VC industry severely lacks gender diversity, particularly in investment decision-making roles, meaning there are fewer women available to choose to invest in women founders. Some women in VC are reluctant to recommend women-led startups because of an expectation that those recommendations would be immediately rejected and potentially mocked, hurting that woman VC's status within the firm.
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Lack of Visibility: See no women, hear no women, choose no women. We have to become unmistakenly, unavoidably visible. To boldly go where no men in authority can miss us.
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Lack of Accountability: Yes, it's 2026 and the diversity and equity climate has changed dramatically. Some leaders feel that it is harder now to proactively search for and choose people for leadership roles on the basis of ensuring a diverse selection. Let's make it easier for everyone. Participate loudly in WiLAI's efforts to bring visibility and accountability for choosing equally (and often better) qualified women for legal AI roles. Calling out the lack of accountability is incumbent on all those in a position of power, including organizations like WiLAI.
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Join us. Support us. Talk about us.
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2027?
How Do We Create Change?
A Few Recommendations
(and the founding principles of WiLAI)
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Build Dedicated Networks: Create networks for women founders and investors, including a women-focused "safe" space. A need for a dedicated, comfortable space for women is a driving force behind the creation of the Women in Legal AI (WiLAI) organization.
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Normalize Women's Leadership in Legal AI: Promote greater awareness and normalize the presence and capabilities of women as the most senior leaders and experts in legal AI. This is the primary goal of WiLAI News.
Create New Models: Creating systems that ensure fairer evaluation processes and support different leadership styles rather than forcing women into existing ones. We can do this together!
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Connect the Most Powerful Women: Enter the Women in Legal AI organization (WiLAI) - created with the goal of joining, supporting, and promotion women Founders, Funders, Lawyers & Leaders.
It is our hope, and expectation, that these senior leaders will shine a light for other women who aspire to follow in their footsteps.
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Help us empower, promote, and support women leading legal AI. Send us your news, write for us, share our stories, and become a Women in Legal AI member.
