The Stack Overflow Podcast

Cassidy becomes a CTO!

Episode Summary

As tech builders, it’s easy to get caught up in the tactical nature of our roles and responsibilities. From meeting deadlines to fixing bugs, we can forget the human side of work. In today’s podcast, Ben and Ceora discuss what it’s been like to return to in-person events after a two and a half year hiatus. Plus, Cassidy announces her new role as CTO and how she is juggling management with mastering an array of new technical fields.

Episode Notes

Ceora shares her experience representing Auth0 at REFACTR TECH, reflecting on what it was like being back in-person after years of virtual events.

Cassidy announces her move to CTO and how her current leadership role at Contenda fits into her career journey and future aspirations as a technologist.

Ben talks about Stack Overflow’s Flow State, the first IRL event he’s attended since 2019 and Stack’s first ever customer conference. 

In case Cassidy pulled you down a rabbit hole of wondering how eels reproduce, check out this piece in the New Yorker from 2020.

Be sure to follow Ceora and Cassidy on Twitter. 

Speaking of the power of curiosity, today’s Lifeboat badge goes to user448810 for answering the question, Feasible implementation of a prime-counting function. Thanks for helping 6,000 people gain valuable knowledge.

Episode Transcription

[intro music plays]

Ben Popper Now, some failures may feel like the end of the world, but at the end you find yourself walking away with a vital lesson. CircleCI CTO Rob Zuber is on a mission to find stories of software industry leaders who survived some epic mishaps. Subscribe today to the Confident Commit Podcast at

BP Hello, everybody. Welcome back to the Stack Overflow Podcast, a place to talk all things software and technology. I am Ben Popper, Director of Content here at Stack Overflow, joined as I often am by my wonderful collaborators, Cassidy Williams and Ceora Ford. Hi, y'all. 

Cassidy Williams Hey!

Ceora Ford Hello! 

BP So I want to kick this episode off chit chatting a little bit about what's been going on with you. Ceora, you got a new job pretty recently and you just did your first live event. Can you tell us a little about it?

CF Yeah! So me and some people on my team all went to Atlanta last week for REFACTR.TECH, which is a tech conference that this year had a bunch of different tracks.

CW It's a big one too.

CF Yeah. It was a bunch of different tracks with talks having to do with software development, career development, ethics in technology, all that kind of stuff. I didn't get to see too many of the talks because I was actually running a table with my team at Auth0. And that was a cool experience, it was a different experience. I've been doing DevRel this whole time during the pandemic, so everything pretty much has been virtual for me so it was my first time getting to experience the typical DevRel thing of having the table and having to tell people about your product and what you do and everything like that. So that was interesting in having to interact with a whole lot of different people. It was fun. It does take a lot of energy.

CW Yes. You get really good at your 30-second pitch though. 

CF Yeah, and that's kind of what I just did. But I don't have trouble talking to people and having conversations and stuff like that, but it was just different. I was nervous at first because I was like, “I'm still new to the company, I'm still new to the product. Are they going to ask me questions that I won't be able to answer?” and stuff like that. But it really wasn't anything too complicated. I mean, the most complicated questions I was getting were like, “What does Auth0 do,” and that was a quick and easy answer.

BP You got that one wrapped up. Nice.

CF Yeah, so it was pretty fun. 

BP Nice. Did you see any talks you liked or run into any folks you know? 

CF Yeah, so I got to meet quite a few people that I've seen through Twitter and never in person, which was cool. The one talk that I made sure I had to see was by Angie Jones and she was talking about Web 5.

BP Whoa. She's just jumping right ahead.

CF Yeah. You know that I've been extra super, super, super skeptical about anything having to do with Web 3.0, so I was like, “If anyone's going to cover this well it's going to be Angie.” And she kind of skipped right over Web 3.0 and kind of took some of the good things about Web 3.0 and the good things about I guess what you call Web 2.0 and combined it together. 

CW Two plus three is five!

CF Yeah, exactly. So it was a really interesting talk. I want to watch the recording because I feel like a lot of it went over my head because half the time I was like, “Wow, this is my first time seeing Angie Jones give a talk live,” and the other half was like, “What? Am I actually warming up to the idea of something new? Is this really happening?” So I want to watch the recording again, but it was a really interesting topic. 

BP Nice. We had Angie Jones on the show and she revealed that she does have a patent on a time machine. So I guess if anybody knows what Web 5 is going to look like, she is probably the one. She just skipped right ahead.

CW She has like 26 patents. She's a genius. 

BP Yeah, she’s a genius. Well that's very cool. And Cassidy, you also have some news to share with our listeners. We kind of maybe spoiled it a little bit, but we didn't get deep into it. You got a new gig. Let's hear about that.

CW I did. And so I have joined the team at Contenda and so I'm going to give a little bit of background. This is a company that I have been advising ever since they started. I actually kind of helped them start the company a couple years ago. And so I know the team really well– I've been having regular calls with them for over a year and a half, just helping them as they figure out what this company is, helped them through pivots and stuff. And it's a cool tool, it's an AI tool that takes content, like for example this podcast, or a conference talk, or a blog post or whatever, and uses AI to repurpose it into something else. So if I give a conference talk, it could generate a blog post based on that conference talk, complete with code samples and everything. It could create tutorials, it could create tweet threads, it could create highlight clips, all that jazz. So it's particularly relevant to my interests as someone who makes a lot of internet content and stuff. And there was a point where in my previous role, I liked the team, I have all good things to say about Remote, but I was kind of missing that DevRel aspect of interacting with external developers that I wasn't really getting in that role. And with Contenda, again, I've known the team for so long and worked with them for so long that they were saying, “Hey, we're getting ready to prep for some new go to market things, some new fundraising things, lots of startup-y things, and we need help on the engineering leadership side,” because it's just something that they haven't really had outside of advisors and stuff. And so it kind of just became a natural fit where I considered it for a while and realized it was kind of obvious for me to go because I like the team so much, the culture so much, and the product so much. So that is where I'm at now. I am their new CTO.

CF Nice! CTO!

CW I know! And so I've been on lots of investor calls and lots of getting a lay of the land. I've got to make tech purchasing decisions which I haven't really done before, in addition to a lot of just engineering management and setting up structure and stuff as the company grows. So it's very exciting. 

BP That is awesome. So you're going to learn a bunch of new skills. This is a big challenge for you and I'm excited. How many folks are on the engineering side? What kind of team are you helping to oversee? 

CW So the entire company is seven people fulltime and then there's contractors. And of all of those, I think only two are not engineers, and that's the CEO and the main product designer and product manager person. And so I'm overseeing all the engineering stuff and this whole past week as I was onboarding I was splitting up responsibilities, like CEO is going to be taking over sales, handling all of the design aspects of everything and investor calls and stuff with a few exceptions. And then my end will be managing the engineering team, figuring out, “Okay, how are we going to get structured as the company grows and how are we going to refine our practices and everything?” So it's a lot. It's exciting. The company is small enough where there's a lot to do, but there's also a lot of cool things to work with and a lot of impact to make. 

CF Wow. 

BP It's super exciting to see you in a leadership role like that. And as you said, the company is still kind of young and just starting out to sort of get customers kind of coming out of a private beta. If in two or three years this is a very successful company and continues on its own, gets acquired or whatever, that leaves you in an amazing position where then you are qualified in many ways for a CTO role at a larger company. So I think it's just super cool and I hope you enjoy it. We'll see. You've never been a CTO before, so you might love it, you might not, but a lot of opportunities, so that's very cool. 

CF This is exciting! 

CW Thank you. It's definitely going to be a learning experience overall, but luckily so far I'm able to fit what the company needs and then we'll see as it grows and changes how that'll work. And again, it's been a very intense week of learning, but in a good way. It's a very good kind of busy that I haven't had in a while.

CF Nice, nice. Is this the company that was based out of Philly? 

CW Yes.

CF [gasps]

CW I know. I’ll get to visit you at some point! 

CF Yeah, nice!

BP Yeah. Our current Chief Product Officer, Teresa Dietrich, started out as CTO and then realized that we needed a CPO, took on that role, and then we ended up hiring a CTO. So I think you'll figure out the role and other people will come in.

CW Right. It’ll morph and change.

BP Morph and change, exactly. Very cool. 

CW Right now it's going to be a lot of both leadership work and individual contributor work just because of where the company size is at, where in addition to running engineering team things, I'm also probably going to be working on the website and those kinds of things until we have everything more structured out.

BP And so, yes, I can see you working on the website and doing great. I know you're a front end stylist and genius. What about the AI/ML stuff? Are you going to have to bone up on that? Are you going to delegate that? How do you learn about that stuff? 

CW So luckily, thank goodness, they have actual professionals at the company working on it. I have worked in AI before and so I know a lot of the terms. There was once upon a time before I dropped out of my master's program that I took some AI classes in graduate school. And so I do know high-level how a lot of ML/AI stuff works, and luckily the tools make it so much easier now. And so there's definitely some brushing up I'm going to have to do, but luckily I'm not starting from complete zero on that front. 

BP Nice.

CF Oh, good, good. I find AI and ML really intimidating so kudos to you for taking it on.

CW It's so interesting.

CF It's interesting, it is, but I feel like it's also– should I say this? I don't want to intimidate anybody listening, but I feel like it’s easy to get wrong so that's why I'm like, “Ahh!” 

CW Well it's interesting because it's not deterministic. You could give an AI tool some kind of prompt and it'll generate something different every time. It's not just like a one seed will always generate this kind of answer, which is very weirdly human almost. And so that's what's kind of interesting about it and especially with making this kind of content because it has to be technically accurate. There's a lot of really interesting problems to solve on like, how do we judge the accuracy of a code sample that's output by an AI if it is potentially different every time it comes out? And so that's been some of the problems they're solving already and it's interesting to see how the approaches have been. 

CW Cool!

BP Right. Yeah, I'm excited for this. Maybe in the future Contenda will be cutting up some highlights for us so that could be very fun. And in terms of what’s going on over at Stack Overflow, I just got back from New York City where we had our inaugural customer conference, first of its kind for Stack Overflow which is exciting. And also, as we were just talking about with you Ceora, first time going to a big event in a while which was exciting. It was something we weren’t certain we were going to be able to pull off. We had to come together and work across a bunch of departments but in the end it was a big success. We had some great speakers; Clive Thompson, author of the book Coders, Dr. Gloria Mark who’s a specialist in human-computer interaction, and then VPs of Engineering from Udemy and Salesforce and folks from Etsy and Indeed. So it was a very cool experience for me to be back in person. I met startup people who had a lot of energy, folks who had arrived in New York City from Ukraine and were building new lives for themselves in the tech world, so it was really energizing for all of us. Lots of great Stackers, customers, and community. And I think to your point, kind of testing the waters to figure out what people want in terms of in-person versus remote. A few thousand people attended remotely which was cool, but we also had a few hundred attend in person which we were not, Ceora to your point, necessarily expecting.

CF I think a lot of people would rather do it in person more than you probably think. Because I think right now at this point in the past two and a half years in the pandemic, I think a lot of people are just point blank period burnt out from virtual events. I'm in Philadelphia so I'm a two hour drive away from New York City and I would rather go to the Stack Overflow event in person than see it virtually because I'm a little bit over the virtual events personally and I think a lot of people feel similarly. So I think that you'll probably see a better turnout than you anticipated, but I don't know.

BP Good. That makes me feel positive. 

CW I think a lot of the talks are valuable at conferences, don't get me wrong. I give them for a reason, I enjoy learning from them. But I think the real value of in person conferences is the ‘hallway track’ where you just get to know people in between talks and stuff. Where Ceora, you mentioned running a table. There's some people who I met who were running a table at conferences two years ago, five years ago, that I still stay in touch with because we had such good interactions in between seeing different talks. And I think that's where the real value lies in those in-person events. Otherwise, if you just wanted the technical content, yeah, I would go online. 

CF Yeah, yeah. 

BP Yeah, that makes sense. And I guess thinking about what do we offer, that was another reason why we have the 360 photo booth and the still-to-be-revealed secret swag that I made which you can take home with you, it's a physical thing. So yeah, that's another reason why you might want to show up in person. I had a big meeting with a bunch of students, like three or four hundred students at a Major League Hacking event, and they were definitely, Ceora, to your point, they were like, “Remote hackathons– not cool. IRL hackathons. We want to be back in person doing the Red Bull, eating the pizza, grinding all night.” So they were hopeful that this year will be the year on campus life kind of really resumes in full.

CW I kind of miss in person hackathons. They were exhausting, don't get me wrong, because you do stay up way too late and it's probably not healthy. But the environment and the energy of trying to hack something together with people around you as everybody is like, “We've got to just make the demo work!” It's a very fun environment that you just don't get when it's offline.

CF Yeah. It's interesting that you both mention hackathons because one of the communities I'm supposed to be focusing on in my new fancy role are students, and that means that very likely I will have to go to hackathons. I've never been to a hackathon before, but in my head I imagine that the way they work is that sometimes you'll have people who are semi-professional and can be mentors to guide people through the process, so I guess that's what I'm going to be doing. So I anticipate maybe we can have a future episode dedicated to talking about my first hackathon experience, because I'm supposed to be doing it in the coming months.

CW I would love that.

CF I think there's one that's happening in San Francisco. Oh my gosh, I'm so nervous about it and I'm not even going to lie.

CW They're so fun, and granted they probably have changed over time, but I feel like I was graduating college in the big heyday of hackathons where PennApps for example in Philadelphia was a huge hackathon of like 3,000 people, and it was just tons of people hacking throughout the night and that is how I got an interview for my first job out of college. That's where I met my now-husband.

BP A life changing event. Wow, cool.

CW Yeah, I know. I think I went to over a hundred hackathons at some point. Because they’re such a good way to bond with people who are, again, hacking together. And kind of like what you said, there's definitely newbs. I think at my first hackathon all I did was install things the entire time. But then over time you kind of get used to the environment and you can just rapidly learn so much. I love it as a fun medium to learn and build. 

BP Right. Then you come in as a pro and you help all the newbs. All right, you've installed this, you don't need that, let's get cracking. 

CW Exactly. 

CF Yeah. So we'll see how that evolves with my new fancy job and all that stuff. 

BP Alright, very cool. I like it. Great episode update on all of our hosts. Appreciate it. One thing I wanted to share that I thought was kind of cool, it's called Plasma Bigscreen, a privacy respecting open source and secure TV ecosystem. This is neat because every TV you buy these days is a smart TV and they often ask you at the beginning, “Do you want us to track everything you watch so we can make better suggestions? Do you want AI-assisted this and that?” And they're often owned by very large corporations and the data will go somewhere else you never really intended. So it’s cool to see an open source version of this where you can surf the web, you can install apps, you can do YouTube, you can do Netflix, but it's built on top of some very well established open source framework. So I thought that was neat. 

CF Cool!

CW I'm genuinely excited about that because it's very frustrating that if I want to update Netflix on my TV I have to sign into my TV and all this. And you don't really have a say in what your data looks like when it comes from a TV. You can't do like a Ublock Origin or any sort of ad blocker thing because it's your TV. And so the fact that this exists is very exciting.

BP Totally. You make a good point which is that the TV is now functioning in a lot of ways like a computer but it does not have that same level of usability if you're the kind of person who wants to fine tune privacy and stuff. And like you mentioned, if I'm installing something new and then I'm signing some terms of service scrolling through with the remote. Who's reading this? 

CW I just want to use my TV. 

BP And then this one. I just have to say it shouldn't be so hard. The length of Earth days has mysteriously been increasing and scientists don't know why. I don't really feel like days need to get longer. Days are the right amount of time.

CF I feel like if days get longer, companies and corporations will figure out a way to make us work longer hours.

BP That extra second. Yeah.

CF And for that reason, I don't like this. If it keeps progressing to the point where we get like an extra hour I don't know what I'm going to do. I'm going to go independent. That's what I'm going to do.

BP Go independent. Exactly.

CW The more I learn about just science and nature things in general, because it's interesting, I do it on the side, the more I realize how much we don't know as humans. And it's shocking to me how much we don't know in general about anything. We don't know how eels reproduce. Just babies show up one day. We don't know.

BP You’d think somebody could follow them and figure it out, but no, it is a mystery for the ages. 

CW It's an actual mystery. That's shocking to me. We didn't know until the past 10 years how whales slept. The earth is a mystery and that's very scary but also so interesting. 

CF Yeah. I kind of feel the same way about computer science and software development. There's still so much of it that we haven't unlocked the potential of. It’s cool, but also a little overwhelming at the same time. But it's cool to think about. We talk a lot about Web 5 and quantum computing, so it's fun to anticipate what it's going to look like in the next 10 years.

CW Right, like someday we will be laughing at an episode like this. 

BP Right, exactly. Why are we doing this episode when our holograms could have been doing it for us? It's ridiculous.

[music plays]

BP All right, everybody. Well, it is that time of the show. I want to shout out somebody who came on and contributed to the community. This week the question was, “How can I work up a feasible implementation of a prime counting function?” which goes ahead and tells you for a certain number how many primes are there above or below it. So we want to shout out user448810, awarded two days ago. Appreciate you coming on and answering this question, getting us a great lifeboat, and helping over 6,000 people with a little bit of knowledge. All right, everybody. I am Ben Popper, Director of Content here at Stack Overflow. You can always find me on Twitter @BenPopper. Email us,, or leave us a rating and a review if you like the show. And just to remind folks, the Flow State Conference happened yesterday. It was really great. I hope you caught it in person or at the live stream, and if you didn’t then we should have some material up about it in a week or two where you’ll be able to go see all of the talks that we gave, both our executives and all the great guest speakers. So when that comes out in the future we’ll be sure to put it in the show notes.

CF I'm Ceora Ford. I'm a Developer Advocate at Auth0. You can find me on Twitter. My username there is @Ceeoreo_. 

CW And I'm Cassidy Williams. I'm CTO at Contenda. You can find me @Cassidoo on most things.

BP Awesome. All right, everybody. We thank you for listening and we hope to talk to you soon. Bye, bye.

CW Bye!

CF Bye!

[outro music plays]