Behind the Scenes of Upper Bound With Stephanie Enders | Approximately Correct Podcast
Approximately Correct: An AI Podcast from Amii · 2026-05-12 · 26 min
Substance score
27 / 100
Five dimensions, 20 points each
Stephanie Enders, Chief Delivery Officer at Amii, discusses the behind-the-scenes operations of Upper Bound, the global AI conference that has grown from 400 attendees in year one to 8,000 participants across five years. The conversation covers how the conference evolved from separating academic and industry audiences to intentionally blending them, the implementation of immersive audio headphones to solve technical and accessibility challenges, and how themes have shifted to reflect broader AI adoption and literacy across education, critical infrastructure, and workforce readiness.
Key takeaways
- Upper Bound uses immersive audio headphones to improve focus, accessibility for neurodivergent attendees, and Q&A quality - solving the #1 complaint about conferences being bad sound.
- The conference deliberately facilitates 'purposeful serendipity' through broad themes, technical labeling of sessions, and permission-based interest matching to help diverse attendees (rockstars and introverts alike) make meaningful connections.
- Key conference themes have evolved significantly, with AI for Education, Critical Infrastructure, and Agentic AI rising as major focuses, reflecting the shift from technical breakthroughs to mass AI adoption and literacy.
- The conference operates with experimental flexibility - constantly trying new approaches and abandoning what doesn't work, drawing inspiration from festival culture and experiences beyond traditional academic conferences.
- Community events surrounding the conference are core to the experience, allowing attendees to deepen conversations about learnings and participate in activities beyond sessions.
Guests
What our scoring noted
Our reviewer’s read on each dimension, with quotes from the episode.
Insight Density
The episode is predominantly a promotional preview of Amii's Upper Bound conference, offering very little that a B2B operator couldn't infer themselves. The handful of mildly interesting observations about conference design are buried in cheerful filler and do not approach the density of actionable, non-obvious insight.
Sounds good. I do love Upward Bound. So m. I'm excited to talk all about it.
the immersive audio gave them the space to take in content, but they still felt energized to do the hard work of the conference
Originality
The immersive-audio headphone approach and its downstream effects on neurodivergent attendees and Q&A quality are genuinely interesting, but they are presented descriptively rather than as a transferable framework. Everything else - purposeful serendipity, mixing academic and industry audiences, iterating year-over-year - is conventional conference wisdom.
we don't leave it to chance
there's no shushing. No one gets shushed at Upper Bound
Guest Caliber
Stephanie Enders is a legitimate practitioner who has actually built and scaled this event, which lends some credibility. However, as a chief delivery officer at a regional non-profit AI institute whose primary expertise is event operations, she carries limited relevance or authority for the broader B2B operator audience this index targets.
I'm the chief delivery officer here at Amy
my time at startup Edmonton, I did work with south by Southwest
Specificity & Evidence
The episode does include several concrete data points and named anecdotes - 8,000 attendees, 200 speakers, the cruise-ship headphone logistics, John Carmack leveling a folding table, the University of Edinburgh guests, Meta's team, and Google.org funding - but these are mostly colour details rather than evidence that supports a transferable argument.
they found like the last 500 available headphones that are coming off a cruise ship. We made the cargo flight by something like less than 30 seconds on checkout
last year we sold out about a week in advance
Conversational Craft
The host asks almost exclusively soft, affirming questions with no follow-up challenges, no pushback on vague claims, and no probing for transferable lessons. The interview functions as a marketing preview rather than a substantive dialogue.
Are you sleeping at all?
what's your like number one Upper Bound survival tip
Conversation analysis
Computed from the transcript - who did the talking, and the verbal tics along the way.
Share of words spoken
- Speaker B81%
- Speaker A19%
Filler words
Episode notes
In just five years, Upper Bound has grown from a 400-person birthday party to one of Canada’s largest AI-centred events, drawing in thousands of people each year. But it isn’t the only thing that has changed: the way we talk about and use machine learning is also completely different in 2026. On the latest episode of Approximately Correct, Stephanie Enders joins to discuss how the conversation around AI has shifted in recent years.
Full transcript
26 minTranscribed and scored by The B2B Podcast Index.
Speaker A: If I were to get you to look into the future, is there a direction things are going? What do you think we'll be talking about at upbound 2030?
Speaker B: I can't believe 2030 is going to be a year like that. Doesn't it sounds so fake.
Speaker A: Welcome back to Approximately. Correct. I'm Scott Lowal, and you are not Alana Fish.
Speaker B: I am m not. I'm Steph Enders. I'm the chief delivery officer here at Amy.
Speaker A: Absolutely. And one of the many, many things you do here is to make sure that Upper Bound happens. Upper Bound is the Global AI Conference that we host every year. May bring in thousands of people from all around the world. And I know that it is a lot of work, a lot of excitement. So we thought, let's get, uh, a behind the scenes look with the expert on what it takes to make up our bound happen and how, uh, things have kind of changed over the last five years.
Speaker B: Sounds good. I do love Upward Bound. So m. I'm excited to talk all about it.
Speaker A: 8,000 participants, I think, is what we're saying.
Speaker B: Yeah.
Speaker A: 200 speakers. Whole bunch of people. Are you sleeping at all?
Speaker B: Oh, I'm sleeping a ton, I think.
Speaker A: Okay. It's good.
Speaker B: The best thing about Upper Bound is that it's like all hands on deck, and it's a thing that everyone gets to see themselves in and build. So I'm sleeping wonderfully.
Speaker A: That's good. It's still a lot of work, though. I mean, I do see you're getting a lot done.
Speaker B: Um, whenever you sell out an event in advance, it can be really exciting. But also it gives you more space to think about how to make the event awesome because, you know, all these people are coming and they have it in their calendars. So. Feeling really great and just so grateful that the AI, uh, community has stepped up in such a big way to sell us out early.
Speaker A: It sold out in previous years, but this was quite a ways ahead of the actual conference.
Speaker B: Yeah, last year we sold out about a week in advance. And so we could see it trending almost, uh, like at the end of February. And then things just kind of took off in March. So we hear everybody, we know everybody wants in, we're doing what we can, but, uh, we're really capped at the physical capacity of the space right now. So if we could welcome everybody in, we absolutely would. We just can't.
Speaker A: This year, you and I were both here for. This is the fifth year, but we were here for the first year. That was a couple hundred people in amy's HQ for some sessions. Now we've got this massive thing. Did you ever expect it to get to this point?
Speaker B: Uh, that's a great question. Well, no, because the first year we did it, it was a birthday party. And so the very first year, it was AI week, and it was a celebration of 20 years of AI research excellence. And we really wanted to find a path to celebrate the people who had invested so much time and really built a legacy when may there wasn't so much focus on AI. And so that first year, it was kind of right after everything was opening, after the pandemic, we welcomed just over 400 people. And it truly felt monumental in that moment. Uh, it was also the opening week of AMY hq. So for folks that have come to see the AMY space, uh, paint was still drying on the walls. We had parts of it kind of cordoned off for health and safety that were still under construction. And then we held an academic symposium off site. And so in that first year, we actually kept our AI industry folks and our technical researchers separated. And so that was a big learning out of year one, was that, uh, that's not really what we were going for. And there's so much we can do to foster community and connection. And so to grow to 8,000 people in five years, I don't think that was on anyone's, uh, wish list. But we kept on growing and responding to what people really enjoyed was deep access to people who think deeply about this technology, opportunity to have real conversations, and then really facilitating a different kind of way of thinking about AI, which is being open to the optimistic possibility of this technology while being super realistic about its risks and the ways that we can approach that. And I think it's created a platform that people really appreciate. So one of true open dialogue, and
Speaker A: I mean, on that point of how it used to be a lot more separated from the academic and the, uh, industry side. I know a big core part about the conference is that it's to kind of create those connections and not have them in kind of different silos. So can you go a little more? Why was that such an important part of Upper Bound?
Speaker B: Yeah, so I think when people come to Upper Bound for the first time, it doesn't look or feel like an, uh, academic conference, but it also doesn't look or feel or operate like a trade show. And it has a lot of these pieces built in for, I would say, purposeful serendipity. And there's good things about that and there's some challenging things about that. So the really good things about that is we don't leave it to chance. And so when we think about producing the conference, we really think about how do we facilitate opportunities for people who might not often meet to meet. And so the very first thing is the structure of the conference. So we have themes that are very broad and then how technical each session is is really labeled so that folks can go to any session they're interested in or feel empowered to go to, but they understand what they're getting into. And then the other piece is there's lots of different kinds of people who attend a conference and there's different ways to meet people. So I think there's those rockstars that can go into any room and start up a conversation, but that isn't everyone. And so we've brought in some technology that allows for interest based matchmaking where it's not just like here, let's open our DMs on M the app and you can slide in and ask me a question. It's actually permission based to facilitate a one on one meeting with a location. And so any of those barriers that we can remove that make it easy for the folks that love to go into a room and have a conversation, we do that in our immersive, um, audio space. So you don't have to ever worry about interrupting someone if you're excited to see someone you haven't seen for a long time. And to the folks who maybe are a little bit more nervous about how to reach out to a researcher or a startup founder for the first time, that we actually create that pathway through uh, a one to one mechanism that's super easy to use.
Speaker A: Okay, and where do those kind of ideas come from? Is that just researching what other conferences are doing or is that, uh.
Speaker B: So I guess personally I have quite a long history of working in spaces that are based on building experiences. And so places in the arts do this really well. So if you think about uh, Edmonton's legacy as a festival city and that there's lots of ways to participate in those festivals, um, I think we draw from that. We draw on the great experiences from kind of Canadian artistic practices like Cirque du Soleil where your experience at the kind of merch booth and in maybe a food hall as part of the experience, not just the performance you're watching. And then my time at startup Edmonton, I did work with south by Southwest and seeing like how they integrate pitch competitions or demos or that sharing of the leading edge with a really large pop culture audience. I think we Draw from lots of inspiration. Um, but mostly we think about, like, our community, the people here, and how can we showcase all of their awesome work and then work backwards from that?
Speaker A: Nice. And as someone who's, you know, been involved for the last five years, uh, I think one of my favorite parts is it's always like, they're like, oh, we're trying something new this time. It's always. It's never always the same, which can cause some excitement, let's say. But it's always fun, like going in and seeing it in action when the time actually comes.
Speaker B: Yeah, I think there's always room for experiments. Uh, I think the, oh, we're doing this new for the first time is often due to a specific constraint or request. So it might be this is the limited space we have, or we're having deep, technical conversations. How do we help people focus so that they get the most of those conversations? Uh, it might be out of the opportunity to bring unique audiences together. So we're always trying something new, um, and we're not afraid to stop doing something. And it's one of my favorite things about the Amy approach is if there's a better way to do it, we should explore it. And so I think that's how we ended up with the headphones.
Speaker A: Could you let us know what that's like for somebody who hasn't come yet?
Speaker B: So for folks that haven't come to Upper Bound, um, a large portion of the conference is under immersive audio. And so I think the places where people typically see this are like cruise ships or silent discos. You'll see them at film festivals where essentially every attendee has their own set of headphones. And you tune in for that direct audio. Uh, when the team at Amy saw this in practice, I think it was first seen in Eaton center during tiff. Uh, folks were watching a movie on multiple floors of an atrium in a mall. Uh, and it was like, oh, well, maybe we could try this, because it could solve the number one thing that people hate the most at conferences, which is bad sound. People hate that. And so if we can find a new way to solve that, why not try it? And so our friends at Encore, who we partner on all the audio visual for the conference, they brought in a test suite. They had us out at an event to test it out. Um, and we, we go big at Amy, and so we thought, well, if we're going to do it, we might as well do it for the whole thing. Um, and so we brought that in and we learned a lot about how important that audio experience was. And so it allows people to really focus. We have a ton of folks that come to the conference where English might be their second or third language. Add onto that a deeply technical talk. Having great crisp audio that you can focus and also tune out the rest of the room is fantastic. Uh, another piece we found is it makes Q and A so much better.
Speaker A: Yes.
Speaker B: And so folks that are on stage actually have really good audio where if you're at a conference, typically all the sound is pointed out to the audience. So it can be really tricky, um, for the onstage people to hear talkbacks. And then it's really awkward if you've never worn an in ear to try to do that for the first time when we were on stage. So the headphones, everybody's used to wearing headphones, so that's been a great experience. And then we got incredible feedback, um, including through an official audit about the pathways for participation for our attendees that are neurodivergent that it allowed for a different way to navigate the space and have focus. The other piece that I mentioned before is nobody has to worry about interrupting someone. And so all the things that happen at Upper Bound, my favorite is there's no shushing. No one gets shushed at Upper Bound.
Speaker A: Always the worst feeling.
Speaker B: Yeah. And it's not that you have to like, I think we've all been there where someone is like, oh, let's just, let's leave. Let's leave and talk about the super important thing and we'll come back. Um, in that big immersive audio room, you're able to slip your headphones off and just have a conversation, slip them back on. And so there's no friction or break in that experience of connecting with the people that you haven't seen for a long time or that you saw them somewhere else on a stage and you're like, oh, man, I really want to say I appreciated that as they're kind of walking by. So that's the immersive experience.
Speaker A: I do have to say, as somebody who is extraordinarily easy to distract, it's so nice to not be sitting there and just hear the door close as somebody comes into a session 10 minutes later.
Speaker B: And yeah, I think all, ah, that head snap to like, who opened the door. Yeah, yeah, that goes away. Um, last year we hosted some guests from the University of Edinburgh who were over to speak specifically about high performance computing. And one of the things that they were excited to share with me as we got through the conference is they didn't feel tired.
Speaker A: Oh.
Speaker B: In like, the best way is that the immersive audio gave them the space to take in content, but they still felt energized to do the hard work of the conference, which is meeting people, making connections, making plans for the future. And it was such a lovely compliment that at first blush, can seem strange. I really like this conference. I don't feel tired. But what it means is that, uh, their social battery was still charged to do all of the stuff that surrounds the conference, which is the most important part.
Speaker A: Yeah, I think we've all had the experience. You know, you get done and you're like, there's more stuff to do, but I just, I need, I need to take a nap or I need to get, uh, away for a little bit. But not, not so much the same way.
Speaker B: At Upper Bound, the immersive audio also allows us to kind of prepare people for the great evening, uh, community event roster. So when I hear that kind of comment around, I'm ready to do more. Um, it means that after a full day of sessions at Upper Bound, I know attendees are excited to go out into all the awesome community events and then meet people who might not have a conference pass, but are still interested in that specific activity. So I think that's another really cool part of what we do, is the integration of the community events, which I think is really core to some of the best startup festivals and conferences in the world, is that surrounding layer of events beyond the conference floor.
Speaker A: Right. Yeah. And it seems like there's been a real enthusiastic. Like we're getting some really interesting community events set up.
Speaker B: I think I. I'm always surprised by which community events come through every year. And I know this year we have a big group coming in from Manitoba to come and share what's happening in AI in Manitoba. I know that the kind of venture community does a ton of community events in the past. There's even been fitness events, so walk and talks or 5k runs in the morning. Uh, not my crowd. Um, but, uh, we've had Zumba one year. So I think it's another signal that the best part of conferences like Upper Bound is the opportunity to have some perspective and have conversations about what you're learning or what you're discovering at the conference, not just to be in the sessions every hour of every day.
Speaker A: Yeah. On the topic of the headphones.
Speaker B: Yeah.
Speaker A: You hear stories around the office, so I've heard one and I got you here. So now I want to ask. There's one involving a cruise ship and an airplane?
Speaker B: Yeah.
Speaker A: What's that about?
Speaker B: So I think, well, every year I think no one's coming to Upper Bound. It's like a well known joke in the office is that like, no matter how many tickets we sell, I'm just like, no one's gonna show up.
Speaker A: We were having, we sold out. And you and I were talking about this.
Speaker B: Yes.
Speaker A: And you said, I don't feel like
Speaker B: I don't think anyone's coming. So, uh, one of the things we do is when demand surges, we really do honestly try everything in our power to make it possible to welcome more people in. And so last year we saw that interest and our great partners at Encore, uh, we reached out and said, like, is there anything we can do to increase the capacity? And, uh, that year the headphones were one of the restrictions. And so they worked really hard. And they found like the last 500 available headphones that are coming off a cruise ship. We made the cargo flight by something like less than 30 seconds on checkout. And the headphones all arrived and our team wiped them all down, made sure they got charged, uh, and they were ready to go. So the immersive audio is fun, but it's also a big lift. Like, we have lots and lots of people making sure that they're sanitized and charged. We're grabbing them off every backpack we see so that we don't run out of headphones for the next session. Uh, but those things are fun, those kinds of last minute pieces. Um, another favorite moment of the behind the scenes of last year is, um, when John Carmack was excited to demonstrate his kind of real time Atari work. Um, that was the group that I had in last setting up their demo tables and so seeing arguably one of the best software engineers in the world kind of trying to level a folding table or asking very nicely if there was a less slippery tablecloth. Those are the moments that ground you into maybe the scale and scope of what started as a celebration of 20 years of excellence. And really taking a moment to pause has become a moment that, um, people are excited to take part in. And it's still strange to think of it being thousands and thousands of people. But, uh, I do believe they will come.
Speaker A: They will come.
Speaker B: In my heart of hearts, I believe they will.
Speaker A: They will definitely come. Like we have a wait list at the moment.
Speaker B: It's true.
Speaker A: I mean, five years, it's a great milestone. What has struck you about how the conversation around AI has changed in those five years? I mean, not upper bound or just in general because it's obviously we're in a very different space than we were in 2021.
Speaker B: Ooh, that's a big question. I think the biggest thing is who we welcome into the room. So in year one, I would say it was pretty research and academic heavy and um, the folks from industry were people really on the leading edge or incredibly curious. And so that's uh, a, I would say it was an unbalanced room. It was probably the first. And the conversation was very, very much focused on kind of interpreting technical breakthroughs for a non technical audience and the beginning of conversations on applied AI. Over the years the conversations have become much more broad and I think you see that reflected in the themes at Upper Bound. And it's this piece of bringing not just folks that are acutely invested in AI and AI frontiers, but all of the folks that are interacting with the opportunities for mass AI adoption and mass AI literacy. And so themes that have kind of started small and gotten really big include um, AI for critical infrastructure, um, big theme this year. It's a huge theme this year. And it started last year, um, as quite a small theme. And as we started to program it it became bigger and bigger as a focus on high performance compute and data centers grew in the local dialogue, the national dialogue, and having great experts who can talk about it from folks building those facilities, the researchers using compute, and then the opportunities for efficiency and optimization. That's been super exciting. Um, one of the most popular and in demand themes is AI for education and AI literacy. So this year we're welcoming that full stack of educators From K to 12 People from post secondary and then workforce training experts, um, to really have this shared dialogue about what is AI literacy and AI fluency as a foundational literacy skill for the future. And then new for this year is we have a whole theme specifically on agentic AI. And so I would say there's lots of opportunity to talk about agentic uh, AI in the past, but they were embedded in different themes and this year we've seen that kind of rise to the top. And then last but not least is time, uh, to shine for technical workshops. Technical, uh, workshops has been a big dream of Upper Bound and we've tried a lot of different ways to facilitate that. This year it's really clicked. And so we have technical workshops throughout the entire conference. And then Friday is exclusively technical workshops and really interesting areas. So we have a team coming up from California, from Meta to really deep dive into a recent paper related I think to Pytorch, um, but then also on the flip side, one of our research associates that's wrapping up their term under the Future Forged fellowship program, which was a pilot from this past year, is leading a three hour technical workshop related to the work he's done over the past year at the intersection of AI and biology. And so I'm really excited to see those technical workshops come to life, uh, in a different way, in a way that we've been hoping over the past five years.
Speaker A: And then if I were to get you to look into the future, I mean, what, is there a direction things are going? What do you think we'll be talking about at upbound 2030?
Speaker B: Oh, upper bound. Oh, gosh. Upperbound 2030, that. That sounds too far in the future. I can't believe 2030 is going to be a year. It sounds so fake.
Speaker A: All right, two years from now, I
Speaker B: hope the things that people started to percolate on, uh, this Upper Bound or last Upper Bound, that would be my big dream for two years from now, is those folks are on stage talking about the thing that seemed impossible or this, the thing that seemed like too big to build. And we do see that already, um, and just seeing that momentum. So I know that we've had many a startup that had come to an early Upper Bound and are presenting and it's a big milestone for them to present at Upperbound after engaging with us really early in their growth. Um, this year, uh, we're doing our first ever one year update. So last year at Upperbound we announced the AI Ah, Workforce Readiness Program and the funding from google.org in a big way. And so to be able to do a one year update and see just the incredible impact beyond what we thought was possible in a year and share it and continue that dialogue. So I think that'd be super cool. In two years is if even more of the conference is kind of building on itself and sharing the fruits of that collaboration or the fruits of that fertile soil that we try to lay
Speaker A: here, like a continuity between the engineers. Okay.
Speaker B: I had no vision for what Upper Bound would be in five years, and I think it went pretty well. And so I think allowing our team to listen to the community and push and think of what's possible rather than to kind of overly prescribe what the future of the conference, it's worked out so far and so I would like to be surprised.
Speaker A: Nice. Well, I'm sure there'll be some surprises. Absolutely.
Speaker B: There always are surprises. Yeah.
Speaker A: And then last question, once while we have you here, what's your like number one Upper Bound survival tip.
Speaker B: Oh, Upper Bound survival tip.
Speaker A: Yeah,
Speaker B: I feel. Well, a. I'm probably the worst person to ask because I don't think I've actually been to Upper Bound, so, like I'm at Upper Bound, but I get just to see the incredible work and dedication of the Amy team and how they come together and support one another and truly have the experience of the attendees, like front and center in what we're trying to do that week. So my survival is really based on a lot of electrolytes and candy and gum, but I don't think hydrated, Keep
Speaker A: that sugar high going.
Speaker B: Yeah. I don't know if that's the survival technique I'd recommend for attendees. Uh, one of the things we do that is unusual is we ask people to leave the main conference site and I think that's super important. So if you're coming as part of a corporate group, there are amazing things happening on site at the Edmonton Convention center for the four days. Absolutely. But if there's something in the schedule that catches your eye that's a five to ten minute walk away, take a chance on it. Um, it's my favorite part of seeing the photos that come back from the conference is all the candids that the team get of people, honestly just having the best time as they walk with other participants that they've just met and that they've identified through a lanyard. Uh, but you can't fake candids and I see that connection. And so, uh, it might be easier to stay at the conference site, but if something's off site of interest to you, uh, just ask if anyone nearby is going. And there's always people like taking over that Jasper Ave, couple of blocks. Um, our friends at Ghostlight Cafe are hosting a number of early morning coffees and then the career fair is literally across the street. It's not that far, uh, at the Brighton block, which is a beautiful renovated historical site in Edmonton. And so that would be like, maybe not survival, but if you're going to take a chance on something, I'd recommend leaving the conference, which might be bad advice for any other conference.
Speaker A: I mean, come back too.
Speaker B: We would love you to come back. Come back, drop in all the time. But that's probably the piece I wish more of our attendees would, would trust us on.
Speaker A: Perfect. Well, Steph, thank you for joining us and giving us your really unique perspective into how Upper Bound works.
Speaker B: The whole team does so much. So I see it seems silly to be the person talking about it, but, uh, it's, it's a joy to see the team do all of the work to put it on.
Speaker A: And, uh, there's a lot to be excited about when it comes to Upper Bound. One thing I'm really excited about is we have a live taping of Approximately Correct. The guest for that one will be Kevin Layton Brown. He's one of our researchers out of UB and he works on kind of the intersection of economics and AI. Uh, it's a really interesting area and if you want to keep up with what we're doing here on the show, you can subscribe. We're at Spotify, we're on Apple Podcasts anywhere you listen to podcasts really. Or you can check out the video on YouTube and, uh, leave a comment there. Let us know what you think. We love reading through all of your comments. So until then, I'm Scott Lowall.
Speaker B: And I'm Steph Enders.
Speaker A: And this has been Approximately Correct.
Speaker B: Sam.
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