Lesbians Who Tech 2018: Hillary Clinton, The Future of Disruption, a Path Toward Hope

I waited in line at 8:00 in the morning. It’s now 10:45 and I am in the front row. At 12:15 today, I will watch Hillary Clinton speak to a room full of queer people, and likely it will be about technology.

Technology is, in part, why Hillary Clinton is not president.

There are no press cameras allowed until after she leaves, so I can’t document how close I am to the stage. But it’s one of those seats where you have to slightly incline your head to see what’s going on. And there’s no one in front of me.

I was at the first Lesbians Who Tech Summit in San Francisco as well. It was an amazing conference even at its start, and the first of its kind. No one could have anticipated how it would grow, least of all founder and leader Leanne Pittsford, who seemed somehow both calm and shellshocked every time I ran into her over the course of the three-day event. In her kickoff speech, where she delivers her customary State of the Tech Lesbians and discusses where the organization has come from and where it’s going, she dropped the numbers and they were astounding: Lesbians Who Tech boasts a membership of 40,000 queer women, non-binary folks and allies (while they center lesbians and the lesbian experience in the technology workplace, their tagline is “Queer. Inclusive. Badass.,” which is why I still feel comfortable taking up space here after coming out as trans) and is the largest queer professional organization in the entire world. The largest, and it centers women. The largest and 50% of their speakers are folks of color. The largest and 10% of their speakers are trans.

Since that first conference, Lesbians Who Tech has always had rockstar presenters: Megan Smith, who was the country’s Chief Technology Officer during the Obama Administration (otherwise known as the last administration I personally recognize before we all fell into a pit); Kara Swisher, co-founder of Re/code and killer technology journalist; folks from Indiegogo and Twitter and Amazon. In the intervening years, we had the pleasure of welcoming to the stage and the squad Edie Windsor, who filed the lawsuit that struck down DOMA and paved the way for legal gay marriage in the United States—and was also an engineer at IBM and the first person to have a personal computer at that company. This year was the first anniversary of Windsor’s passing, but she’s remembered in part by the Edie Windsor Coding Scholarship, a program named for her that helps queers go to coding schools. Lesbians Who Tech has had rockstars all the way down.

But the experience of Lesbians Who Tech’s New York Summit in 2018 was a whole new level. Aside from one person from Goldman Sachs who basically only told us how great it was to work for Goldman Sachs, all the presenters I experienced were not only rockstars, but were compelling speakers. And they were speaking on a loose theme of leadership. Each Summit has a focus, and this time around there was a heavy emphasis on what it means to be a boss. This, I think, resulted in a more curated attendance and a more intimate group.

Dom DeGuzman, DevOps and Technical Program Manager at Twilio, scrapped her presentation at the last minute to talk about what leaders really need to do to lead a team (answer: you need to bring the passion, and not every project will be your baby — so make that passion about the people and the process; find the things in your team members that they do not yet know they can do themselves and use every project to foster those things). And she did it flawlessly; she made it look easy to scrap a talk and wing it.

Lanaya Irvin, Director at Bank of America Merrill Lynch, spoke about how she has, for the past decade, had two closets: her normal closet and her “Condoleezza-Rice-Wear.” That being a black lesbian who is “unapologetically black and gay” in a leadership role in finance has, often, forced her to hyper-feminize. She has recently decided not to continue doing that — she was wearing a Jenna Lyons-esque black suit. Everyone cheered.

Andra Keay, Managing Director at Silicon Valley Robotics, outlined in very clear detail how we as a society can avoid the Robot Apocalypse — spoilers, the first rule is “don’t build killer robots,” a rule that the United States actually refuses to explicitly agree with at the UN. I feel like this is a good rule; I wish my country also desired to not build killer robots. I began to realize that leadership, in the context of this conference, also occasionally meant stewardship: the idea that we will leave this planet in some sort of state for the folks who come after us. That, as the engineers, designers, thinkers on the bleeding edge, we need to not only lead within our organizations, but we need to be thinking about leading the world. In what sort of world do we want to live our lives?

Jane Lynch—well I’m not sure what she was doing there, but dang I enjoyed hearing her speak. Apparently the costumes on The Marvelous Mrs. Maisel are as luxurious and wonderful as they look. If you want to really hear about how technology has impacted the entertainment industry, I’d suggest looking up Mara Wilson’s and Gabby Dunn’s views on the subject. If you want to hear Jane Lynch scream “fuck you” at her Apple Watch for telling her to stand up, then brill, this was the right fireside chat for that. And, I think, a nice breath out in the midst of all the very hard stuff we talked about for three days.

I begin to realize that because this conference is largely about leadership, perhaps Hillary Clinton won’t be speaking about technology. I am immediately a little sad at the thought, but I try to wipe that sadness away, because a) who doesn’t want to hear about leadership from Hillary Clinton and b) she’s already given us a book about What Happened, do we really all need her to relive every shitty moment? That’s just… mean.

I try to concentrate on the speaker at hand, try to be present (though that’s hard for me—my Ravenclaw-brain is always whirring). It gets easier, though, because the person on the stage is Madam Gandhi. Former drummer for M.I.A. and electronic music performer, she came on stage and valiantly performed using audio equipment that was not set up for music (her mic went out at one point and she elegantly tapped it and looked at the sound people while continuing to rap). But music isn’t all Kiran Gandhi does: she spent time at Universal Music analyzing performance for the label’s artists on YouTube and Spotify, determining whether one million views in a weekend was a triumph or a disaster. She also got her MBA at Harvard while touring with M.I.A., which prompts me to turn to the person sitting next to me, Leah Fessler from Quartz, and say “holy shit.”

Madame Ghandi at Lesbians Who Tech NYC 2018

The point of Madame Gandhi’s presentation isn’t, I think, what she actually intends for the point to be (though at one point she says “optimize for your own joy” and I scribble it down in large letters). I actually think the point of her presentation is that one must unapologetically advocate for the things they want and step ahead into those big plans with a fierceness. She talks about her boss, how she watched her former boss walk into these male-dominated industry spaces and change things, bring other women up. It’s why she went to business school.

The consensus from the Summit seems obvious: leaders have to bring other queer folks up once we get to the top. In the past, it was called an “80’s mindset” a couple of times by a few different speakers, the idea that there can only be one. But when it comes to a diverse workforce, the technology industry at it’s most cis-hetero-normative seems to think both that diversity is required and desired, and also a risk.

I am used to this.

I am used to this outside the technology industry and in it. It’s just subtler in other fields; the assumption as my body walks into a space and it is inherently unprofessional. I am used to cis-men, colleagues who have known me for years, assuming I am less intellectually rigorous than they are. It is a risk to employ any of us, common wisdom says. And I look back at the room full of queers at my backs — all employed, all at a summit focusing on leadership, all in an industry that is, at times, overtly hostile.

“If I’m going to stand out anyway, I might as well have fun with it,” said Andra Keay at an AMA about robots. She was in possession of the most spectacular undercut, the long hair on the top dyed beautiful galaxy colors. This was during a supplemental stage session titled “Leadership Lessons & Pro-Tips for Being a Boss,” moderated by LaFawn Davis, Global Head of Culture and Inclusion at Twilio. Our very own Raquel and I had seen her on the main stage earlier. When she walked out, I gasped at how badass she looked: leather pants, the most gorgeous pink top with fashioned-fabric rose epaulets, purple hair. And every word out of her mouth was as badass as her presentation. “We lied,” she said, assertively and badassly, regarding the Silicon Valley attitude of bringing one’s whole self to work. Her point was that no one was equipped for that — that’s why the millions spent on recruiting folks with intersectional identities had barely moved the needle. “It’s not just who’s coming in the door; it’s who’s walking out, too.” When the industry was ill-equipped to support these hires, they left. It’s not a pipeline issue; the talent is there. The Silicon Valley just punishes people for bringing their entire selves to work at the same time as telling them that they should. People like Davis are trying to fix it.

One of the most brilliant, hope-giving parts about being the writer who’s covered Lesbians Who Tech fairly consistently since the first Summit is watching the evolution of discourse at the bleeding edge with forward-pushers like Davis. I remember when we were talking about a pipeline problem; I watched it morph into the inkling of a support problem; I was watching when the organization announced the Edie Windsor Coding Scholarship in response to the idea of pipeline and support both being issues. And at this Summit, they’re talking almost entirely differently about the ways the industry has failed. It isn’t a problem of education, or of children, or of marginalized communities’ failure to stick with it; the industry, according to this discourse, actively punishes people for being who they are after asking them to be who they are. As Rumman Chowdhury, Global Responsible AI Lead at Accenture, said of algorithms, they push everyone toward normalizing, toward a center. The algorithms cut out the outliers. The Silicon Valley has been pushing their workforce toward homogenous; technology folks even write it into their programs.

“It isn’t about making sure everyone has a seat at the table; we need to redistribute those chairs.” Everyone claps and cheers and hoots and I do too. I look over at the journalists covering the event and they do not seem to display emotion like this. They are professional and smart and buttoned up and I am, once again, a human cartoon. I wonder if I appear unprofessional. Then I remember I am in a sea of professional people who are often seen as unprofessional, who push back against their environments daily, and I tuck that feeling back in my pocket to interrogate later. I also remember I am not a journalist; I am a writer who occasionally does some reporting for their stories. The rules are different; I laugh big and cheer loud and participate, because I don’t ever think I can or should be objective. I don’t ever think I can or should distance myself from my community.

We are listening to Kimberly Bryant, the Founder of Black Girls Code. She is being interviewed by Tiffany Dockery, Senior Product Manager at Amazon. And what’s more, Bryant’s daughter is also on stage; Kai Morton was instrumental in the founding of Black Girls Code as well, and has recently started university. She’s also gay. Watching these two be a family on stage is amazing and endearing.

“We only have we,” says Bryant, of lifting up Black women, of making community with Black women. It’s a statement that applies to this room in all sorts of intersecting ways. I don’t identify as a woman anymore, but we are a room of risky people. People whose bodies arrive in a space and the assumption made is of our incompetence. And yet here it is, the largest queer professional organization on the planet, full of powerful people taking care of each other. These are the people who buck the algorithmic trend toward center, toward normal (and what normal means is, often, cis-hetero-patriarchal).

And then it is time. Kara Swisher comes on the stage wearing a cashmere flannel and carrying a bottle of Rodham Rye to introduce the fireside chat between Leanne Pittsford and (Rightful President) Hillary Clinton. Later I will see Pittsford outside the venue and I will ask her “how do you feel?” and she will look back at me and say “I have no words.” But it is not later. It is now. And Clinton is walking on stage. She waves and I take a few cellphone camera photos, as I’m not allowed to take out my nice one. I send one to Carmen Rios, who texts back “OMG.” I send one to my family. I send one to my best friend. I am very excited to be in the front row watching Hillary Clinton high-five Leanne Pittsford.

Hillary Clinton high-fiving Leanne Pittsford, via Lesbians Who Tech’s Twitter

Leanne asks her first question and Clinton puts the microphone up to her mouth to speak; the mic is dead. The entire audience reacts. It wouldn’t be a tech conference without some technical difficulties. But I am close enough to the stage to hear Clinton turn to Pittsford and crack a joke: “Oh no, the Russians are here.” I am not the only one; the front four rows roar with laughter. Pittsford hands over her mic and we are off to the races. The interview is fairly soft in tone; there’s not much that’s hard-hitting to ask in front of this room, where I have not met a single person who self-identified as a conservative to me (and I talk to everyone).

Pittsford asks about October 7th, 2016 — a lot happened that day, it was a never-ending hit-parade for the press. President Obama announced that Russia had been tampering with the election; the Hollywood Access tapes came out, in which Donald Trump brags about assaulting women; Wikileaks dumped the DNC emails. Pittsford lists everything that was happening on that day and then asks Clinton: “So how was that day for you?” The audience laughs. I laugh.

Clinton regrets not being able to make the media stick to “Russia has been interfering with our election” for at least 48 hours. And then she says, “Wikileaks is a wholly-owned subsidiary of Russian intelligence now. It wasn’t always that way, but it is now.” I grab for my phone to Tweet it, because I love hearing this woman speak truth unapologetically and I am a millennial who performs excitement on social media. I have strong feelings on how to leak; feelings that have grown and changed a lot. The technology sector often has quite the boner for “total transparency” as though that, alone or at all, will solve the world’s ills. What they neglect to account for is the bad faith actors with zero investigative training that make up a large portion of the populace. Something Clinton has experienced firsthand. Of the false facts and fake news and specifically of “Pizzagate,” in which the DNC is accused of running a child prostitution ring out of a pizzeria basement, she says, “Look, the pizzeria doesn’t have a basement.”

I look over at Fessler, who’s posting a photo of Clinton to Twitter. I write in huge letters in my notebook, ARE YOU POSTING PHOTOS? And she nods. I feel emboldened, even after the Lesbians Who Tech staff made a huge deal out of my camera. I post a fairly terrible photo, but I don’t care that it’s not great photography. On this day I listen to Hillary Clinton say that the Russians are still at it; they’re still all up in our electoral system and we don’t even really know what’s coming. I want to remember that. I want to remember that I am aghast as she says that Republicans spend 40% of their advertising budget on digital media and Democrats spend 0-15%. I scribble down “tech for campaigns” and later I will look it up. Later, as I write down my experiences, I will encourage any queer with technology skills to get matched with a Democratic Campaign they can help. I will also encourage queers to get into hobby robots because Andra Keay told me to. I will do it in the same paragraph.

Pittsford is now asking a question befitting of a leadership summit that focuses on women. “The more powerful women are, the more they are disliked,” she says. “You’ve experienced that, probably more than anyone in the world.” Clinton answers this gracefully — women need to support women who challenge the double standard, she says, and women are often treated poorly when they pose a threat to the established order. It’s one thing if you have a problem with the quality of a woman’s work, I hear her say, but the instinct is to insult her personally. To call into question her likability. “The knee-jerk reaction is ‘Oh, she’s just not that likable.’ But I have a list of about 10 million men who aren’t particularly likable. We need to get over that.” The room erupts.

But inevitably, we will all discuss how likable we found her. We will talk about how funny, how it’s nice to see her loosen up, like it is important when it certainly is not. We will talk about how Pittsford asked her what technology questions she calls up Chelsea to ask her, and Clinton will sigh heavily, the word “yeah” escaping her lips and we will all laugh. She will make a joke about how, if it looks like her messages are disappearing, she gets a little paranoid. She is grace personified. And I know we will talk about this because my original idea for coverage was to interview attendees and in the moment I did not yet know that everyone would be too busy figuring out how to save the world to talk to me, so I am making a point to ask everyone what they thought. Likable, personable, loose. And later, when I will write it all down, I will ask myself if we were all also falling into the trap (myself included), or if we hoped that, in that room with us, with people who had her back, everything was just a little bit more special because that’s the way it felt, it felt special?

But it is not later, yet, it is now and Clinton is categorizing Donald Trump’s behavior. “I wouldn’t say disruptive, because disruptive can be positive… he’s more than that.” She is talking, of course, to a whole room who has a particular notion of the term “disruption.” It strikes me. I honestly expected Clinton to be a lot more bitter about the term “disruption.” I know I am. I think the technology sector has taken disruption a bridge or thirty too far, with no concept of what should be disrupted and why, rather disrupting only what it collectively sees it can. The idea that everything is a thought experiment. The idea that because most of the folks who make up the technology sector won’t feel the consequences, that the consequences don’t exist. That is what I hear when I hear disruption.

Once again I consider the room I am in, and how many of these speakers have explicitly talked about their own forms of disruption. How many have risen in the ranks and then decided to blow up the mold into which they used to contort themselves to fit. Pittsford is asking rapid-fire questions now, meant to be fun. “Pantsuit or tracksuit?”

“Pantsuit, obviously.” Clinton looks at the audience because we are all in on the joke. We cheer and I think about the data feedback that we have found ourselves dealing with. President equals men’s suit, men’s suit, men’s suit, men’s suit. Woman equals likable, likable, likable. And here, in this room, we have the outlier. We have so many outliers. The data that breaks the algorithm. And maybe we aren’t there yet, but as this room grows internationally, we will get there. We will pull ourselves away from being normalized.

The only politician’s answer I really hear is to the question “is Facebook a utility?” Clinton sidesteps answering a pretty hairy policy question by stating that, if she remembers correctly from her interview with Kara Swisher, Mark Zuckerberg thought at one point that it was. It’s an elegant way to point the audience in a direction without committing. But I tuck all that away, too, because it is understandable that skilled politicians might give this kind of answer every now and again and Hillary Clinton is very, very good at her job. I choose, instead, to hold onto the feeling that I have seen the future of disruption, and it is not the tacky, gold-gilded Trump brand. It is here. This is where disruption is headed. And that gives me hope.

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A.E. Osworth

A.E. Osworth is part-time Faculty at The New School, where they teach undergraduates the art of digital storytelling. Their novel, We Are Watching Eliza Bright, about a game developer dealing with harassment (and narrated collectively by a fictional subreddit), is forthcoming from Grand Central Publishing (April 2021) and is available for pre-order now. They have an eight-year freelancing career and you can find their work on Autostraddle (where they used to be the Geekery Editor), Guernica, Quartz, Electric Lit, Paper Darts, Mashable, and drDoctor, among others.

A.E. has written 542 articles for us.


  1. “I began to realize that leadership, in the context of this conference, also occasionally meant stewardship: the idea that we will leave this planet in some sort of state for the folks who come after us. That, as the engineers, designers, thinkers on the bleeding edge, we need to not only lead within our organizations, but we need to be thinking about leading the world. In what sort of world do we want to live our lives?”


  2. I really like your take on this, what you bring out. This especially : that when we walk into a room, we’re seen as _less_ of everything. There was always something nagging at me, I think that might name it.

  3. Awesome overview, so thank you for that. One minor point of clarification: the US does not currently support a ban on lethal autonomous weapons or, colloquially, “killer robots,” because such systems could hold the potential to reduce civilian casualties and/or increase compliance with international humanitarian law. I say “could” because the systems don’t exist yet–and also because there is no internationally agreed-upon definition of them (i.e., it’s not clear *what* we would be banning or whether banning whatever-it-is would have a net-positive or net-negative impact on IHL/military utility). Also, the U.S. isn’t disagreeing with the UN, because there is no UN-position on the issue. A number of states have argued that it is premature to discuss banning a thing that doesn’t exist and has not even been defined yet.

  4. We are “The data that breaks the algorithm”

    What a perfect phrase and what a wonderful mental image it gives me <3

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