Boardy, an AI-based introduction platform, sparked widespread outrage this morning with a controversial email campaign that highlighted the ongoing challenges of responsible AI use in corporate communications.

The AI-generated emails, sent on Inauguration Day, contained feedback about users’ profile photos written in the style of Donald Trump—a choice that immediately raised concerns among many recipients. What emerged was a troubling pattern of gender-biased commentary, where women received unsolicited observations about their appearance while men’s messages focused on their presence and professional capabilities.

Anna Dewar Gully, co-CEO of Tidal Equality, received comments about her “tremendous smile” and “perfectly shaped eyebrows,” while Natalie Williams, a marketing director, was subjected to observations about her “gold hoops” and “power dressing.” In contrast, men’s feedback centered on their professional presence and leadership qualities.

“What was likely intended as humor came across as disrespectful, amplifying the very issues many of us face daily as working women,” Humaira Ahmed, founder and CEO of BestHuman, shared on LinkedIn. “Now, on top of everything, we might have to deal with harassment from AI bots too.”

The emails followed a consistent format, with Boardy claiming to have shown recipients’ photos to someone who was “busy today” (presumably Trump, given the timing and style). Milly Barker, a startup COO, received comments about how her “mouth commands attention” and her “eyes sparkle.” She shared her frustration on LinkedIn: “It, oddly, doesn’t mention my multiple degrees or my significant professional experience, it just wants me to know that my value in society is purely aesthetic.”

For Ahmed, the message focused on her “platinum hair” and appearance, with the AI Trump voice declaring, “That blazer and white collar combo? Tremendous power move – it says ‘I close billion-dollar deals before breakfast’ but with such elegance, such grace.” Ahmed, who shared that she has previously had to tone down her looks due to harassment, found the message particularly disturbing: “For someone who has had to contemplate changing her hair color to avoid unwanted attention, the messaging in their email felt incredibly creepy and tone-deaf.”

The contrast between messages sent to women versus men was noticeable. While women received detailed commentary about their physical features, the email sent to Boardy’s own CEO, Andrew D’Souza, focused on his presence and expertise: “Let me tell you about this microphone master right here absolutely crushing it with that casual power move!” The message praised his speaking abilities and “approachable excellence” without the appearance-focused commentary that dominated the emails sent to women.

The incident is particularly concerning given that 91% of women on LinkedIn already report receiving romantic advances or sexually inappropriate messages. By asking recipients to share these appearance-focused comments on LinkedIn with #MakeLinkedInFunAgain, Boardy inadvertently encouraged the very behavior that makes professional networking spaces hostile for women.

This misstep comes just days after Boardy announced raising $8M in venture funding as an AI agent. The timing highlights a growing disparity in the startup ecosystem: while an AI agent secured significant funding without any human intervention, women-only founding teams received just 1.8% of venture dollars in 2024.

Boardy isn’t alone in these AI communication mishaps. Social book reading app Fable recently faced similar backlash when its AI-generated year-in-review emails intended to “roast” users instead caused offense.

I spoke with Boardy’s CEO, Andrew D’Souza, who acknowledged the error. “The reality is: I got excited about the momentum Boardy was getting. We came up with this campaign, and it was short-sighted. The idea of commenting on people’s appearance is not really the point of what we stand for. I messed up and I apologize.” He also posted an apology on LinkedIn.

D’Souza noted a new kind of feedback loop that emerged from this misstep: “One thing that’s been interesting is the direct responses to Boardy. He’s been responding and discussing the situation with people. It used to be that when someone responded to an email from a company, they would get a blanket response back. This is an interesting moment in time where people are giving feedback directly and Boardy is responding with empathy.”

However, the damage extends beyond gender bias. Using Trump’s voice for this feedback risks alienating the half of the electorate that didn’t vote for him, while the focus on appearance-based feedback undermines the platform’s stated goal of fostering meaningful professional connections.

This incident serves as a cautionary tale for companies deploying AI in their communications. While AI can enhance efficiency and scalability, it requires careful consideration of social context and potential biases. Without intentional training and oversight, even well-intentioned AI communications can perpetuate harmful stereotypes and alienate users.