Pride at Udemy: It’s not trivial (but there is trivia)

When I started at Udemy in 2016 in San Francisco, I did what most people do when they join a new group — I looked for my people. 

Someone on my hiring panel must have had my number, because I didn’t have to look far. There was a board game night my first week, a karaoke outing my second, and I quickly found a Slack channel for LGBTQ+ Udemates. Udemy, as it turned out, was full of people who were full of curiosity and passion, unselfconsciously excited about their work, hobbies, and communities. People didn’t seem worried about being perceived as too earnest or about conforming to stiffly traditional ideas of professionalism.

Nearly six years later, it’s still true. As we head into Pride Month, I think few events better capture that blend of earnestness and nerdiness than our annual Drag Trivia event.

Drag Trivia first came about as the amalgamation of two strong Udemy traditions. Our San Francisco office typically celebrated Pride by hiring local drag performers to perform and teach Udemates about their craft and its history (because hey, we love learning). On the trivia side, many folks regularly teamed up to compete at bar trivia — known as “pub quizzes” by our Dublin folks — and our Culture Crew ran quarterly in-office trivia nights where randomly grouped teams competed for glory and goofy prizes.

It was only natural when in 2018, we combined the two for “Gays, Beignets, and Q&As,” a Pride-themed trivia night. We served food from a local queer-owned business and adventured through questions on LGBTQ+ history, current events, and pop culture. Bay Area drag royalty Bebe Sweetbriar and Chico Suave commanded our All Hands stage to serve as MCs and performers. Winners got stickers that said, “I Know Gay Stuff.” 🌈 (The stickers were originally a joke, but in true Udemy fashion they inspired some very serious friendly competition.)

The COVID-19 pandemic necessitated a change to the event.  Live drag is an art that’s difficult to cram into a Zoom window. Hosting trivia for teams huddled around tables is not the same as hosting for a wall of tiny, isolated faces. But we made it work. Our drag stars became video producers, crafting routines that fit the new format. We used breakout rooms and Google Forms to reformat the game and preserve the inter-player interactions. People had fun (or at least, they told me they did).

The new format had other benefits: being fully virtual meant we could open up participation to our colleagues in Denver (and any insomniacs in Dublin and Ankara). It let us introduce new round formats that aren’t possible with a pen-and-paper game, like a GIF-based visual round and a guess-the-song round that had our drag guests lip-syncing for their lives. 

Now, with the return to the office underway, we’re excited to preserve the best of our virtual events while reintroducing some of the great stuff from the Before Times (read: beignets). We’ll spend the lead-up in June sharing educational content about queer history and culture, both on Slack and in-office monitors. When trivia night arrives we’ll keep the game on Zoom, letting remote folks team up and play while providing in-office folks more of the “bar trivia” experience with food and drinks and live banter with the host. 

It’s new territory. We’ll learn a thing or two – we always do.

I’ve been helping run Drag Trivia for five years now, and it’s one of my favorite moments of the Udemy year. I love working with and learning from our amazing drag performers. I love watching my colleagues get curious and a little too competitive. I love discovering new things about my community as I research and write questions — historical figures I didn’t realize were queer, LGBTQ+ artists to add to my personal playlists, and global news about gay and trans rights. And I love that six years and thousands more employees later, we’re still doing this. 

If you’re an aspiring Amy Schneider or Mattea Roach (shout-out to our LGBTQ+ Jeopardy! queens!), check out a few questions from Drag Trivias past below. To reveal the answers, simply highlight the text area next to the A:.

Q: The names of the artist behind the album “Channel Orange” and the author of the novel “On Earth We’re Briefly Gorgeous” share a common word. What is it?

A: Ocean (Frank Ocean, Ocean Vuong) 

Q: Caster Semenya, a decorated runner from South Africa, has found herself at the center of controversy (and the subject of hyper-targeted rule changes) around the role and regulation of what?

A: Testosterone

Q: What undersea villain was directly inspired by drag legend Divine? Unfortunately, Divine passed away in 1988, so never saw the character on screen.

A: Ursula (The Little Mermaid)

Q: What country, whose capital shares a name with California’s third-largest city, became the first in Central America to legalize same-sex marriage with a May 2020 Supreme Court ruling?

A: Costa Rica (capital: San Jose)


One last trivia question: Want to work with curious, creative people that value diversity and have fun doing it? Look for opportunities here.

About the author

Katie Bent (she/they) manages Product Instructor Marketing at Udemy. When Katie isn’t dreaming up new ways to help instructors help learners, they’re probably singing their heart out at choir rehearsal, gallivanting through a park with their very big, very good dog, or racking up a tab at a local pub trivia (best categories: geography, classical music, animated TV/movies). Katie served as co-chair of Out @ U, Udemy’s LGBTQ+ Employee Resource Group, from 2018-2022.