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What It Takes to Lead DevRel Teams with Cassidy Williams

Erin and Brian are joined by Cassidy Williams who’ll discuss her path into developer relations, including leading it at multiple companies and how it factors into her to her current role as CTO. Plus we’ll offer our spicy takes on some hot topics around DevRel.

Featured Guest

Cassidy loves to make memes and dreams and software. She’s currently the CTO at Contenda. She’s worked for a variety of companies, large and small, advises startups, and she’s had the honor of working on the board of various non-profits. She’s active in the developer community, and one of Glamour Magazine’s 35 Women Under 35 Changing the Tech Industry and LinkedIn’s Top Professionals 35 & Under. As an avid speaker, Cassidy has participated in many events including the Grace Hopper Celebration for Women in Computing, TEDx, the United Nations, and hundreds of other technical events. She wants to inspire generations of STEM students to be the best they can be, and her favorite quote is from Helen Keller: “One can never consent to creep when one feels an impulse to soar.” She loves mechanical keyboards and karaoke.

Hosted by

Erin Mikail Staples is a very online individual passionate about facilitating better connections online and off. She’s forever thinking about how we can communicate, educate and elevate others through collaborative experiences.

Currently, Erin builds community and thinks about the philosophy and tooling of the community and developer advocate world. Much of her day is spent empowering individuals to build, foster, and embrace healthy communities. Outside of her day-job, Erin is a comedian, graduate technical advisor, no-code content creator, triathlete, avid reader, and cat parent.

Most importantly, she believes in the power of being unabashedly “into things” and works to help friends, strangers, colleagues, community builders, students, and whoever else might cross her path find their thing.

Brian Rinaldi leads the Developer Relations team at LocalStack. Brian has over 25 years experience as a developer – mostly for the web – and over a decade in Developer Relations for companies like Adobe, Progress Software and LaunchDarkly. Brian is actively involved in the developer community running virtual meetups via and in-person events as President of Orlando Devs. He’s also the editor of the Jamstacked newsletter and the author of a number of books.


Brian Rinaldi 0:05
Hello, everybody. Thank you all for joining us, I’m Brian. I’ve got Erin here, my co host and our special guest. Cassidy Williams. Welcome, Cassidy.

Cassidy Williams 0:18
Thank you so much for having me. I’m so excited.

Brian Rinaldi 0:21
Yeah, you get to be our first official guest on the show. So, you know, we just like I’ve mentioned to you earlier, we just started this up last month. As you know, both of us feel like we, you know, we’ve been in that role for working. Deborah, we have a lot to say about that. Well, we have lots of friends and deverill. And we just thought it’d be great. A lot of fun.

Cassidy Williams 0:44
And a lot to say about pickles.

Brian Rinaldi 0:46
A nd a lot to say about pickles, which is

Erin Mikail Staples 0:47
you have a lot of opinions about pickles and DevRel. And I mean, Cassidy, you are someone who actually taught me that DevRel was a career. So I’m, like a flashback moment, because I didn’t know it was a real job for the longest period of time. I was like, you know, and I shared it in the last episode, like I went from product to dev or product to community, like developer community on total accident total unintentional and panic Googled. And your name was someone who came up a lot when I was in my panic googling phase of 2019. What do I do in this job? I have no idea.

Cassidy Williams 1:22
Is this real? Yeah, it’s, it feels like a new job, even though it isn’t. Because I feel like yeah, there just isn’t that awareness. It’s something that like, if you were to major in computer science, a school probably isn’t going to tell you that this is the career path to go into or something just because it’s just new enough that you don’t see it as often.

Brian Rinaldi 1:48
Definitely speaking, which, we want to kind of talk a little bit about how you ended up in a row. Yeah, cuz I, you know, first of all, like, we could go into a long list of all the things you’ve done, and all the things you currently do, like Stack Overflow newsletter, worked for code pen for a while as well. Amazon, and now you’re a CTO, you’ve kind of like wound your way through Netlify Dev Rel, and then moved on to CTO. Yeah. So you’ve kind of like, you’ve definitely had the full Dev Rel experience, the various levels. So So tell us a little bit about how you ended up as endeavor. Yeah. Started, how you ended up?

Cassidy Williams 2:35
Yeah, I honestly started all the way back in college, where I was majoring in computer science and planned on being a software engineer. And that was that was my plan. And I was really, really involved on campus where I was leader of computer science club, and I was really involved with women in science and engineering, and all of these different organizations. And I really loved going to hackathons. And speaking at meetups and stuff, it was just something that I got really, really involved with in school. And I remember when I was applying for jobs, I was just asking, like, Is there something I can do that lets me continue this kind of work like the does that exist? And most places said, no, they’re just like, oh, yeah, you can you can talk at like a meetup or something. If you work here, like, like, it wasn’t really a part of any rules or anything.

So I was kind of just applying and seeing what might happen my senior year. And then I went to, I went to a hackathon. It was I think it was Penn apps was the hackathon, which for anybody who has been in the hackathon scene for a while those that I think that was an is like a really, really large student hackathon. I just started talking to some of the companies that were sponsoring the event. And I was just like, what’s your job? What, what do you do here? And it turns out some of those people that are just like, oh, this is my job, actually, like, it’s part of my job to help developers build better and stuff. And that’s kind of how I discovered what the role was. And this was, this was 10 years ago now.

Brian Rinaldi 4:06
So yeah, it was like 2013, when I discovered that this was an actual career paths that people could get into. And so I started as I was, again, applying for roles. I started saying, Could I do you have a developer developer advocate position or developer evangelist position developer relations, so there was goes by so many different names. And then my first job out of school was at Venmo. And Venmo was very, very early on in those days. And so I was their first advocate, pushing their API and everything and because none of us fully understood the role, I was also doing software engineering at the same time on the app itself. I burnt out a lot that was a that was a very busy well, but that’s that is kind of how I got started. And so from federal I went to small startups, big startups, big companies like Amazon, like you said, Companies like Netlify, and I’ve been doing DevRel ever since. And even in my current role atmthat we’re building a tool specifically for dev roles. And so even though it’s not necessarily my full time role anymore, right now, it’s still very much a part of

Yeah, I think, you know, first of all, when you say you’re so old, some of us when you’re talking about getting out of college, what, like, 13 years ago, you said like,

Cassidy Williams 5:35
no, yeah. 10 years ago, is when I discovered the role. So yeah,

Brian Rinaldi 5:39
yeah, I’ve been I’ve been in the role. Yeah, for 13 years. I was a developer for like, 12 years before that. So yeah. Anyway, I’ve got more old than you

Erin Mikail Staples 5:50
gonna say. The 5, 10 and 15 going on here? Because I’ve been out of college. Yeah. 2015.

Cassidy Williams 5:59
Oh, yeah. 2014 was me. So there you go.

Brian Rinaldi 6:04
Y’all are making me feel old.

Cassidy Williams 6:06
Really? You’re so old? Brian.

Brian Rinaldi 6:08
No, I know it. So. Okay, so. So I guess my question would be curious, given that path that you took, because you actively sought out the role, like, I mean, you know,

Cassidy Williams 6:23
right. When it barely existed? I think Twilio was really the main company that was doing it at the time. And the only one that had like, a job description for it at that point.

Brian Rinaldi 6:33
Yeah. I mean, there was some people that like there was because Google had some

Cassidy Williams 6:37
Yeah, Google kinda did. One of my interviews was at Google, and yeah, like Twilio? SendGrid, that lots of companies. were touching on it. But I feel like Twilio really was spearheading a lot of it at that point. Yeah.

Brian Rinaldi 6:52
Yeah. I think I think Twilio did did kind of change the way it’s, it’s done. But I’m curious how how did the job end up like the actual career end up? Different from maybe your expectations as like somebody who was looking into it had a college?

Cassidy Williams 7:09
Yeah, I think overall, the whole field has kind of changed over time where it, especially because of the pandemic, I mean, the past the past three years have changed a lot of different stuff. But back back then, especially 2013/2014 time, it was really just like, it was very, very event driven, where I was going to conferences, hackathons, and meetups constantly, and that was that was it. It wasn’t like recording videos, or podcasts or making content as much as it was just being in the room all the time and traveling a lot and being a presence in a lot of spaces, which there’s still elements of that. But it does feel like that isn’t the number one thing as much anymore. And it definitely kind of transformed over time into more.

How do you make things more like evergreen, where it’s not just you gave a talk at that conference, good for you by where it’s you gave a talk at this conference. But it is a blog post now that you were able to write about that conference and what you spoke on, or you recorded a video that or you have podcast episodes that people can refer to and that sort of thing. So I do think that the strategy overall has changed over time. And in those early days, for quite a few years, I was traveling so much to go to so many conferences and meetups and events and everything. And now, I’ll still speak at them and stuff. But once again, things are more virtual now. And now people will prefer doing live streams from the comfort of their home a lot more and doing a lot more of the stuff where you can look at it async because that’s kind of the direction the world is going in.

Brian Rinaldi 8:50
Absolutely. Yeah, that that job I used to cut like that was the road warrior. Yeah. It’s and I think some people still do it.

Cassidy Williams 8:59
People do.

Erin Mikail Staples 9:00
I’ve definitely seen it. And it’s interesting, having entered the space. My first community title working with developer communities was 2020. I was doing stuff unofficially, or was like a user experience person or user ID user experience and user research. So I was still very involved in it, but in a different side of things. So like I didn’t have I see people move into the space and they’re like, completely new. And I feel like I had a little bit of an event advantage to that. Because like I already was like, Oh, I know how to do the user research. I know how to be a product manager. Right? Like on this side, instead of like being like, here’s your pain points. I’m like, Hey, let’s let me go celebrate the wins. And like, I’m not going to follow that ticket anymore in JIRA. Oh, darn. Like, it’s got to kind of feel like I’m a fun time now.

Like, I joke that I went from following tickets to making tickets or breaking our products more. That’s, that’s fun. That’s the fun part. Um, and so, but like, even in those years that I’ve done it, you know, now kind of turning the corner you’re Are you going into your four? It’s really an you know, I say that explicitly with in relation to titles. But in that time, I have never really done the road warrior thing, like a lot of it was using User Groups or bringing people to me or, and I’ve done conferences and I’ve done the season, but it’s like, okay, you’re traveling for two weeks, but then you’re, it’s more about the evergreen content or find out, I never studied anything technical. So they find out I have a journalism background, and they’re like content, journalism, background content, and like, you write them like, okay, got it. Got it.

Cassidy Williams 10:35
Yeah. Yeah, my, my last job before the pandemic. And it’s actually kind of wild because the company shut down exactly three years ago today, I think. But I was I was at a company called React Training, where we were teaching, we were teaching React, and the road warrior thing was real. It was a full time traveling job where January 2020. I was home for one weekend. And then that was that was pretty much the one time where I was home. And I was just going back to back to back to back travel, because that’s just what you did. I was teaching workshops, and I was helping people learn react, and I was speaking at conferences, and it’s a very different worlds. Now,

Brian Rinaldi 11:13
do you think, on that note of being different worlds, do you think? Because I always felt like a certain point that has diminishing returns like, right, this is expensive to like, participate in the seriously, particularly if you’re sponsoring, and then the travel and,

Cassidy Williams 11:30
you know, travel, lodging food? Yeah.

Brian Rinaldi 11:33
And so like, it’s a very high cost thing. And then, like, I could show up, and I have no control over when I get scheduled or anything. So like, I show up, and if I’m up against, you know, a Cassie Williams. And suddenly might sound like an I might be speaking to like a roomful of like, 10 people. And we spent, like, you know, so much money, too much money to get me out there to speak to 10 people? I mean, do you think that’s part of the change? Companies kind of realizing that? Or do you think it’s just really been a shift in the mindset of like, backfill…

Erin Mikail Staples 12:12
I can’t I’m sorry, I also was gonna say, I was gonna interject one part, I want to tag on to the back of that question as well, which is, who owns that events? Strategy? Because I think that’s the conversation we don’t have enough is like, you know, I’ve always in my time, I’ve like, if I’m in community or developer relations, I know that my, a lot of my effort is going to do a lot of that direct outreach to reaching out to people that’s time consuming in its own. And maybe is that a marketing function? should not fall under DevRel(ish)?

Cassidy Williams 12:45
Right, relish? Haha, you brought up the name of the show? Well, I think it’s, I think that’s where the lines have gotten a lot more fuzzy. Because with a, again, the shift and strategies and stuff, it has become less marketing II and more, like under its own umbrella as an entity of of several, but I think what events were such a major part of it, it involves marketing spend, in addition to DevRel spend. And so it was kind of like a co strategy type of thing. And I think the the one thing that I really miss about the constant in person events and things that were I’m like, I don’t think they’re going to go away fully, ever, is that hallway track in between conferences, the conference talks, where there might be, there might be a point where, sure, there’s like the really, really big companies like I don’t know that Twilio is of the world was was massive budgets.

And then there’s a small company that might compete with them, but they’re still at the event. And you could still talk to them. And you might learn something that you wouldn’t have normally learned because you’re not Googling and specifically, or you don’t necessarily see them, we’re in one of the last events that I did in 2020. I, for example, I met the MCSE team, there an API for making video stuff. I knew nothing about that. I didn’t know that they existed, but they were at the event, and they had socks, and I was like, I want free socks, I’ll talk to them. And to this day, I’ve interacted with them multiple times over the past few years on content at different conferences at so many things because I had that human connection in between talks. And I so I do think that there is a place for that where Sure, there might only be a handful of people that actually attend your talk, but you’re still in the room with a lot of people that could end up being really fruitful relationships over time.

Brian Rinaldi 14:36
Very true. I’m not thinking they’re gonna go away. I just I feel like, like I see a different purpose. Yeah, I see far fewer of the companies with like, used to be different, at least to me, like early on. It was like, it was all voted warriors. And I was I was kind of an exception being somebody who wasn’t that I might do like, half and doesn’t like it between six and 10 conferences a year, which wasn’t anything like what they were doing, and, and I focus more on content. And so like that was, I felt like I was a rarity, those jobs were hard to find. And now I think it’s kind of flipped. And it’s more about content and less about the road warrior. Right.

And which I think is generally more accessible to where like, yes, you need to be able to, like, have a camera and like have have a setup that allows you to record high quality audio or videos or anything like that. But that is much easier to buy a plane ticket for everything and a sponsorship for about the same cost per second that will last a lot longer. So it’s, it’s an investment, for sure. It’s kind of just depends on your

Yeah, I guess some of us like, wish we were road warriors, Ally says she got to be a road warrior. And it makes her sad.

Cassidy Williams 16:06
I don’t know if it should make you sad also. Hi, Ally. I think I’m glad that I did it. But at the same time, I’m just like, Man, I can’t believe I did that. That was exhausting. You burned out hardcore when you when you have so little time at home. And you’re just constantly going because and there were so many times where I couldn’t make plans with friends because I was just like, I might have a hackathon that week, or I might have a conference that weekend or something. And so I just wouldn’t do it. And I was so bad at taking vacations and stuff in general, because there was always some other events on the horizon that took precedence.

Brian Rinaldi 16:46
I’m personally glad I never did, partly because, like when I started, I already had kids. And young, and like, it’s just not a lifestyle you can maintain when you have kids. So you know, just because my wife works. So like we’re, you know, one of us has to be home in the evening. Sometimes she worked in the evening, as she travels a lot more a lot more than me. She’s the road warrior. But, you know, it just wasn’t it wasn’t possible if, if I had to, to live that lifestyle, it just never would have been out of the question for me. So thanks.

Cassidy Williams 17:25
Yeah, I saw that it should be closer if you can’t hear me till it’s gone.

Erin Mikail Staples 17:30
Thanks, Ally for the tech check. But one of the things I’m like thankful for both of you is like I am feel very, like I’m probably about sitting about four or five conferences, travelwise per year right now, which I’m happy with. And then a lot of them I’m in I have the privilege of being in New York, which I totally get. There’s a cost of living in New York, but I do think there’s something to be said for having people that live in New York or San Francisco or like Seattle, because like, there’s events I’m going to that are like, Oh, it’s in New York, like okay, I’ll just go bebop down. They’re like, Iwent to like, take the A train. I’m like, oh, let’s take the A train. Like there’s an event I’m going to in Boston, and it’s like, to our Amtrak like okay, but it’s so much less of a cost for me, and the way that we’re two person community team right now.

And so we divide, like, we have one person on the West Coast and one person on the East Coast. And so unless it’s a major event, like we’re considering pi con, or like, one of our major events is here, one person’s dividing and conquering, which makes it very flexible, very friendly, very easy. But I mean, I’m also I feel very privileged that I because like, I don’t know that I would sustain the road warrior lifestyle, especially as someone who I, you know, very much admire all the work that you’ve done Cassidy with, like, having 17 Different pursuits, like, you know, and like having all the different like, things to pull on. And that’s just not possible when you’re doing a lot of the road warrior thing. It’s at least for me, like I know, myself, that’s one way…

Cassidy Williams 18:55
It’s really hard. And I do think that like, again, pre pandemic, there were a lot of companies that did have larger teams that would strategize that way being like, we have some person East Coast one person was because someone Midwest would like London, UK and stuff, so that you could go to a more nearby place, Taylor that I don’t want to talk to you. But I know that there’s some great events in your area, where we’re like, it was so nice when you had a team that could be spread out that way so that the traveling was a little bit less painful. But if you were doing Deborah had a really small startup. It was all you baby.

Brian Rinaldi 19:35
Yeah, absolutely. So I have speaking of DevRel, I mean, you you I think we’ve all kind of been at this small startups. Like I think, you know, the experience, in my mind limited experience with it. In its small startups is very different from another company where I feel like a small startup, your like, oftentimes, the first non technical like non technical non, like, developer engineer role? Yeah. Different though. Like, it’s like, okay, we don’t have marketing. So we’re gonna hire a demo. It’s a demo reels, marketing and marketing ops and, you know, in all these different like, all these different positions, they’re the documentation writers and they’re the, you know, it’s I think it’s a very different experience. I mean, if you both agree,

Cassidy Williams 20:32
very different. And that was actually something where one of my roles that I had in the past was being working with a VC firm, and to advise their startups on DevRel, and everything. And so many of the times they’re just like, Devil does that right, and they didn’t fully understand it. And I would have to say, oh, what you need as a technical writer, oh, actually, you just need a marketing person or a social media manager, actually want a community manager, like, there’s so many different things that they would expect. And you kind of have to really define that early and make sure like, if, for example, you want to go talk to a startup and work at a startup, you have to know exactly what the scope of your role is going to be. Because no matter what, you’re going to be wearing lots of hats, if it’s a small team, but if people don’t understand what DevRel is, and then they’re just like, go do it, you’re gonna be you’re gonna have a hard time. And you definitely want to be able to, to define those guardrails so that you just don’t burn out constantly.

Brian Rinaldi 21:34
Totally, totally. I think that’s just the guardrails in terms of like, what the role is, but also in terms of expectations of each other, like, I’ve done it, and I’m like, okay, yes, I can send your newsletter and manage your social media. I’m fine just wearing a lot of those hats. But keep in mind like this, these are not areas that I’m necessarily an expert. So I can do it. But don’t expect the level of results of somebody who is, you know, is gonna, actually knows what they’re doing. Exactly.

Erin Mikail Staples 22:07
I had a really great actually shout out to Matty Stratton because he gave me this advice when I was kind of moving upwards in my career, and I was starting to have that like, Okay, I was at, you know, a former job, I was approached and asked, like, what don’t you want to do? Or what parts do you really want to lead into in your own personal growth, and he gave the advice of DevRel, the minute that someone else is assigning you your role, where they have to ask you, what you’re doing is when you lose value in the company. And so being very working in public and being very clear of, what are you working on? What are you doing? And what value are you bringing, and what is your core KPI or initiative that you’re tackling, that’s when you can really succeed.

And he really compared it to a working dog, which is like, you know, if you’ve had dogs, or, you know, you, if you don’t, if your dog or a puppy doesn’t get into something, and you don’t give them a task to do you, we now have like, I have a 10 month old puppy, and he currently has eaten part of our bookshelf because we left him unsupervised during a nap. And, but it was like, if you don’t give the proper assignment or proper direction, that’s when something is going to happen, or you’re going to get into trouble. And so I think that having that initiative of like, okay, this is my core initiative. And really, almost establishing it as like a pro or a con really helped me kind of like, unblocked to that next level, in my own personal career track, which is, again, I say that like hearing the both of you talking like Cassidy really relating to like, how you’re leaning on, you know, understand and be very clear about kind of what you do, do, but I’m very curious. And it’s something that I’ve been like, kind of there like, I’ve you know, I do it when you’re keycap set, I’ve kind of followed your content, I love what you’ve created.

I’m excited to be like everything’s going on. Yeah, it’s actually I felt that I should have changed out my key caps for this. But how do you balance all of the things, and especially in DevRel, where you’re a very public facing person, I know that I’ve gotten that critique in the past of like, can you be focused if you’re doing comedy? Or can you be focused if you’re doing this other thing? And it’s like, what I do outside my nine to five, just because it is also online? Does that impact you?

Cassidy Williams 24:25
Yeah, how do you that’s a conversation. That’s a conversation that I’ve had so many different job interviews and companies and stuff because it’s, it’s true, and then people are just like, oh, because you do work that’s kind of adjacent to your day job outside of the nine to five. That means you’re always online and working. Excellent. And so definitely setting setting those kinds of boundaries and stuff is is tough, but important because that that’s just kind of the nature of the beast, especially if you do any sort of content or anything adjacent to your role and one thing that I always talk to every company that I interview with is just like what how do you feel about side projects, and I have a doc that I keep updated of these are all the side projects that I’m doing at any given time. And saying, like, are you okay with me doing these things? Because if you’re not, I don’t know if this type of role is going to work. And I’ve gotten to a point where luckily, I can be pretty clear about that, where I can say, like,

Yes, I write the StackOverflow newsletter, it’s not going to cut into day job time. If anything, it might put our company name on the map a little bit, because lots of people read that newsletter. And that could be good for you. But it’s one of those things where I have to be have to be very, very clear about it. And I think being clear about that is so important early as well, just because a lot of companies kind of assume they buy your brand. You’re your own personal brand in some way. And sometimes people are just like, Yeah, I don’t care. I don’t really use social media and stuff. But then others are just like, wait, but my Twitter account stays with me after I leave the company. Not that I’m planning on leaving company anytime soon, but I don’t want it to be just like she’ll, she’ll she’ll shill. And then I bounce and then there’s nothing there again. And so it’s it’s something that I straight up get in writing every single time like these are the things that I do outside of work sometimes might overlap with some work hours, but I will always make up for time that I do so that there’s that clarity there. Some companies don’t like that, and I don’t work for those companies.

Brian Rinaldi 26:36
Yeah, I’ve had that same conversation at multiple, multiple companies, because I’ve been running for five and a half years. Yeah, multiple newsletters, I’ve run conferences and psych. You know, all those things, I think are beneficial to my day job. Ultimately. You know, some companies are like, less enthused about that stuff than others.

Cassidy Williams 27:03
Like, quick note, I think DevRel managers who get DevRel are just like, Oh, great. Yeah, no, keep doing that. Because they understand the value of it. And that it sometimes takes time. Go here. And sorry about that. Yeah, I

Erin Mikail Staples 27:16
was gonna say no, you’re all good. Thank you. I was gonna say, I love that point on managers, because that has definitely been a make or break with some managers. And, you know, there was places when I was last looking for a job that like definitely butted heads on it. But you know, I have a now page that has much like you, like, has everything that I’m working on at this current moment. And I originally started it out of like an ethics assignment that for part of the journalism school that I work at, but kind of kept up and maintained it because I’ve held it’s really important to disclose personal bias and what I’m working on. But even that, like being said, I keep like my contents open. And it’s interesting, because it goes both ways. Because I do have a career as a comedian, and I do get paid for comedy.

I have had people ask if I would do my comedy work for free at their tech event. Oh, and I’m like, No. Like, this is my hobby away from Tech. Also, some of these aren’t necessarily like, I tried, not that I tried to keep the brand separate. But like, I say, we’re bringing brand but like, they don’t necessarily mesh. But the other. The other thing that I found is really, really interesting doing side projects is I’ve never had any issue with people with any of my techie work. But I have had issues because I worked in journalism, specifically political journalism. And really, and so some companies when they were like, don’t talk politics at work in a very like kibosh on that because I have been public about it. I did have companies that were like you need to remove out from your work. And I was like, I’m proud of that work. I did. So too bad. Like, I don’t think this is gonna be fun. But yeah, that’s an interesting.

Cassidy Williams 28:51
That’s a funky dynamic. Yeah. For sure.

Erin Mikail Staples 28:56
It feels weird, because I’m like, okay, but you’re okay with every other tech thing that I post, like, right? And or you want to be comedy like?

Cassidy Williams 29:03
Yeah, yeah. Again, that’s people trying to own who you are. And that’s just not. That’s, that’s not great. Great.

Erin Mikail Staples 29:13
Oh, got a lot of questions from the audience coming in, as we kind of

Brian Rinaldi 29:17
Yeah. Ali Ali actually mentioned like that she something we wanted to talk about. Yeah. So So you, you were obviously working in Devereaux, and then you moved up to lead the team at Netlify and have since moved on to CTO. So I have a couple questions related to that. First of all, based on your experience, obviously, like you’ve you’ve led Dev Rel a couple companies. And what’s what’s the big difference between being like the head of Dev Rel versus being a kind of practitioner of dev rel?

Cassidy Williams 29:57
I see. individual contributor. Yes, that So much more meetings. Because I feel like that’s, that’s, that’s a really high level, clear answer to that. Whatever, whenever you lead anything, it means that you are in meetings. And that was honestly probably the biggest thing. Then when I when I went from individual contributor to manager director at nullify was just in meetings all the time, I kind of burnt out from the meeting sets. that’s ultimately why I left I still love that team. And I was talking with them five minutes before the show like they’re, they’re really awesome people. But I was just, I was in meetings all the time, as a combination of like, okay, yes, we can try to prioritize this versus prioritizing that it was a lot more company strategy type stuff, figuring out how do we want to strategize over around content, which events do we want to prioritize? How do we want to handle these, these budgets and that sorts of that sort of thing. And so that’s, that that is honestly the main difference. It’s much more high level of like the planning of the overall strategy of things versus applying the strategy and doing it. And I admit, I do like, just applying the strategy and doing it a little bit. But I think that’s also why I really liked going to start up some the, the startup a Mac contender, we’re less than 10 people. And I love that I love being at a really small team where I can still do the like hands on work, but then also help on the strategy side of things as well.

Brian Rinaldi 31:38
That makes sense. And so me, do you do you feel like your current role as CTO is significantly different than then you’re what you did leaving deferral or does it?

Cassidy Williams 31:54
It’s definitely again, when when you’re at us very small startup, you were so many different hats. And for a little bit of context of how I got to this role, because I saw that that was a question in the chat as well. So contender is a company that I’ve been advising for a really long time, they actually had their two year anniversary this past weekend. And I’ve been advising them for a year and 11 months. And so like I’ve been advising them from for a really, really long time. And they build AI tools for content creators and DevRel teams and technical marketing teams. And so for example, if we took this live stream and put it through the content of AI, it would output a blog post about this live stream, or tweet thread or highlight clips or things like that. And so it generates content from existing content. That’s the shill spiel thing.

Brian Rinaldi 32:46
I like that.

Cassidy Williams 32:49
you should use us, let me know. So they they started, they started a while ago, I was advising them for a long time. And we kind of gotten to a point last year where I was talking with them so regularly about just technical things, content, things, several things, that it just kind of started to make sense. What if I just joined full time because I’m talking with them so much. And it would just make sense to join full time. And so that’s, that’s kind of how it happened. And because of the experience I had with leading DevRel, just leading in different spaces and engineering management experience, and that sort of thing. That’s kind of how the role of the title came to be. And so on the leadership side of things, I’m going into lots of like, VC meetings and sales meetings and stuff. I’m managing the engineering team, which is everybody except for two people. So that I do one on ones with everybody. Until last month, I was the only front end developer as well.

So I was also building the entire front end for the product. But we hired someone and I’m so grateful for it. And really, if you’re here, thank you for existing. And, and now then I’m not doing all the front end work for that I’m doing more dev rally stuff to where I’m writing more content and blog posts of actually using our product making videos and generating content from that and that sort of thing. And so that’s high level, what my role is and how it came to be. And it’s definitely been very different. But it’s it’s really cool to be on a small team that’s working for several folks and building tools that I would personally want to use in a day to day job and seeing DevRel people who I like use it and be like, Wait, this is awesome and

Erin Mikail Staples 34:44
super cool. I’m gonna say yeah, I was gonna say one of the things that I like hear that I’m like, this is super exciting. I’m very excited for it. But I’m also like, if someone was like, Aaron, you could move up the ladder and you could be like, CTO I’d be like, holy cow. I’m Gotta go shit my pants and like, but what skills did you take from dev rel? And like, really apply that and like you’ve touched on it briefly. But has there been holy cow, I wish someone was here to hold my hand for this, or things that you learned along this process, it’s a little bit different in that CTO realm.

Cassidy Williams 35:20
Yeah, I think, luckily, a lot of my experience aligned really well with the specific role in that, I have done engineering management before, not just like at Netlify. Whereas leading Dev Rel stuff, but also just previous jobs. I’ve been an engineering manager before. And so like the management side of things I know how to do, I’ve done like, the performance review things before and the budgeting things before that sort of thing. I think, because I’ve done so many startup advisory things, and then just worked with VCs, the fundraising conversations, I understand how those work. And like the political dance that happens with that. And so I get that, that luckily, played into the role as well. And then, on the technical side, I know how to code. So that kind of works out. And I think, again, in general, because I had been working with the team, part time for so long, I just knew who they were. And so the dynamic worked really well with that team.

And so it’s, it was kind of a weird hodgepodge of skills that just worked. And I feel like if anybody out there is interested in doing some kind of CTO role, I do recommend kind of dabbling in the different avenues and lanes that you might be touching. Because it’s good to be technical, but you have to think about that people side of things, too. And also, I just like the political dances, but the the political things of what VC looks like and what budgeting looks like, and that sort of thing. And for advising startups, that’s something that I didn’t even know that you could just do until, I think right around when the pandemic started, and I was talking to someone who is his full time job is just being an advisor to startups. And he kind of introduced me to like, Oh, here’s how you can kind of put yourself up for advisory roles and that sort of thing. And that kind of led me down that path, which was really helpful as well. Yeah,

Brian Rinaldi 37:14
that’s cool. I didn’t even know that was a possibility.

Cassidy Williams 37:17
Yeah, it’s, it’s really fun. Because you can like, like, companies come to you and say, we’re thinking about doing X, Y, or Z, which one should you pick? Or which one would you pick? If you were us? And I’d say z. And here’s why. And then we’d discuss it and then they just go build it. And it was awesome. So it’s one of those things where it’s like you can you can really help guide a direction. And then products work in the way that you kind of hoped. And just hear a puppy.

Brian Rinaldi 37:49
Yeah, sorry. I thought Krisp was supposed to get rid of that. Usually does.

Erin Mikail Staples 37:53
That sound good? I was gonna say mine’s currently snoring on the couch.

Brian Rinaldi 37:59
Yeah, at least not eating your your cabinet there. Yeah,

Erin Mikail Staples 38:04
he’s nice. He made it off the bookcase today off to you know, Gremlin activities of another sort. It’s hard being a puppy.

Brian Rinaldi 38:11
But he has arrived.

Erin Mikail Staples 38:14
Oh, wonderful. It’s like I’m like I need this. How do I get this? The verse the button? That’s like the sneaky bow.

Cassidy Williams 38:18
Just like bubble tea to arrive. That sounds amazing. I know.

Erin Mikail Staples 38:22
I keep trying it. It’s like I’m like

Cassidy Williams 38:25
I’ve got this empty cup that keeps showing up. Come on.

Erin Mikail Staples 38:29
I know. I know. There’s gonna be the SOS please. shared office partner my office mate. Okay, my husband wears the coconut Lacroix like

Brian Rinaldi 38:43
Erin I think we had a couple questions from the audience. Right?

Erin Mikail Staples 38:46
Yeah, anyway, sorry for that.

Oh, I think for the first one, like, what? Fist off I’m going to toss us with and from Joshua Garcia. How do you juggle DevRel and writing papers on quantum mechanics and I will toss in if you’ve done YouTube, you’ve done keyboards you’ve done this so many other things like how does your brain manage at all and I’ve been a huge fan of like, watching kind of some your talks to see behind the scenes but if you could break down what is the typical day and Cassidy look like and yeah, projects.

Cassidy Williams 39:25
Also Josh’s a friend of mine, a major troll who always asks me about quantum mechanics. I don’t know anything about quantum mechanics.

Erin Mikail Staples 39:31
I’m gonna say no, I love that. I was gonna say like, wow, that’s so cool, because I’m like, more even more. Yeah.

Brian Rinaldi 39:43
I knew all her side projects, but I didn’t…

Erin Mikail Staples 39:46
I’m pretty sure I haven’t heard that side project yet.

Unknown Speaker 39:49
He’s probably just like cackling by himself right now. Anyway, so but in terms of side projects, and everything that are not quantum mechanics Honestly, I just keep a really strict calendar and I tried to obey it were like I, I set aside time, specifically throughout the week to do all the things that I want to do. And I think by following that it has really kind of kept me accountable to myself a little bit where, for example, every Wednesday at a certain hour, I read the StackOverflow newsletter, even even if it means I have to put it off later in the day, it will happen on Wednesday. And I have like a meeting time for that. And I, I’ve kind of made myself and use a variety of different tools where if I’m really stressed, I use just a paper notebook and write down like, this is my task list for the day.

Cassidy Williams 40:42
Otherwise, I have this app that I made for myself called to do meter that it’s truly just a To Do app with a progress bar. But it works for me. And I put in like this is these are all the things that I want to do for the day, whenever I put it off, there’s a pause button. And then it just goes into like a do later section. Otherwise, everything on that list I have to do. And then that’s that’s truly just where it all is. I use obsidian for taking notes. And I tried to do all of the things in Obsidian. So it’s all in one place. And then raindrop which I talked to you about this before there’s a red drop is for bookmarks, where I categorize and organize every single link and thing that I can enter Raindrop. And I think between all of those tools, and then the last one is Centered. I really love Centered. It’s it’s also a glorified to do list app, but it has like a flow state tracker where you can hit start, and it’ll play like the ambient music to help you focus. And then you can add a web extension that’ll say like, should you be on Twitter right now? And stuff like that. And so it kind of directs your focus a little bit. And I need that sometimes. And so between all these things, that’s that’s kind of how it all gets done.

Brian Rinaldi 41:53
I think you already answered it.

Erin Mikail Staples 41:55
I was gonna say you answered like, the favorite tools do DevRel because like, Centered sounds just like a version of I use the app, which I say has the idiot alarm, which is the should you really be on Twitter via Twitter right now. Because it does. It’s the Pomodoro style and then it gives you a break time. But then it gets really loud.

Brian Rinaldi 42:17
Yeah. I tried that. I tried Centered. It didn’t work for me at all. Yeah.

Cassidy Williams 42:26
Do you need someone more mean?

Erin Mikail Staples 42:28
I need like the Yeah, I’m like, I need the like the idiot alarm of should you really be doing this like the very loud. And it shows up in your what is it called the menu bar up at the top of your Mac?

Cassidy Williams 42:39
Yeah, it shows. With Centered, you can choose different voices. I am one of the voices on there. But like you could have Kent C. Dodds saying like, Hey, you should stop. Or like various other people in the tech industry or or not in the tech industry. There’s there’s just some really funny people who make little voice packs that you can use to yell at you when you lose focus. And it’s genuinely helpful for me, because sometimes I’ll just block off on my calendar, like flow time, and it’ll just go through my list and I kind of just stay focused on that task at a given time. Yeah, I

Brian Rinaldi 43:15
think it didn’t work for me. Because, I mean, maybe this is how I want partly why I ended up in DevRel. I don’t know. Because I just, I’m like, I’m kind of all over the place constantly. My my thinking time is often, like I get stuck, and I just switch tasks to something sort of mindless. But yeah, I’m like processing it before I go back. Like okay, I think I got it now and I’m ready to go back. But, but I if you watch me and like this is why I don’t stream me coding becaus it would be a torturous exercise to watch with. It’s like I’m switching things all the time. I just don’t stay focused, but but to get the stuff done

Cassidy Williams 43:15
That’s what matters in the end. Yeah,

Brian Rinaldi 43:16
I do follow what like your, for my side projects. I always have like, I have a very set time when I do it. And like I’ve even found I always use I’m usually averse to working at all on the weekends, but like, that’s my time for like I found like Sunday morning I wake up and I’m like, okay, that’s my time to do CFE stuff. Like that’s usually when I do all this stuff for this site.

Cassidy Williams 44:23
Yeah, that’s, that’s when I write my newsletter, or Sunday evening because then I’m just like, I’m kind of ramping up for the workweek to start and then I ship it whatever Sunday night and then go to bed.

Erin Mikail Staples 44:37
Yeah, I need the Sunday the Sunday and by the way we’ll drop all the links for sharing them currently in discord right now there’s a link somewhere in this I’m like it’s a down beside or the bar depending on how your YouTube streaming preferences. But I’m the IRS dropping all these links in there so you will have them for later. But yeah, I’m very much a Sunday night worker as well as And I’m getting better at the calendar blocks. I used to avoid it for the longest period of time. Yeah, the unfiltered Real Talk section of why we’re not a professional branded podcast. It’s the currently on the Loki, ADHD medication shortage, there’s been the struggle. So it’s been the nine to five, like, I’m never someone who will work a nine to five. And I’ve been very explicit with employers about that, like, the idea of working at night like logging in right at 9am. And logging out at five terrifies me. And that’s never how I’m gonna do my best work. But I’m usually like, I will do a 730. And then I might take a workout in the middle of the day. And then I might do this, and then I will be back on it tonight. But you don’t want to see my work after me staring at it for three hours. Because I did that last week. And I had to build a Slack bot. And I broke it four different ways because I copied the wrong API code. Because I was trying to do it in a very stupid, easy fix that it was like one of those ones, you come back to your computer and you’re like, you idiot.

Cassidy Williams 46:04
That hurts my heart? Don’t get me started. But it’s real. It’s yeah, that is actually something that once again, I love about startups, because they tend to be more flexible about that, where on our team, we’re kind of just like, you know, I need to go for a walk. And then we just kind of let people know. And as long as people generally know, can I contact you now or not? That’s that’s kind of how we operate. And it’s, it’s nice to have that sort of flexibility at work. Because then if, for example, you’re just like, this is a side project day. I don’t think I could do it. You make up the time, but as long as things are done by a deadline, that’s what matters.

Erin Mikail Staples 46:40
Yeah, absolutely. Fortunate? Yeah,

Cassidy Williams 46:44
we’re very spoiled and tech.

Erin Mikail Staples 46:47
very spoiled.

Brian Rinaldi 46:48
We are but Elon Musk is here…he’s gonna take it all back, right? Going back. I love that there was like a New York Times or Washington Post article about like, how all the tech CEOs behind the scenes were like, rooting for him because they thought we were all spoiled.

Erin Mikail Staples 47:07
But so I did interview one place and I’m not gonna name names, but they were that was one of their non negotiables is that I was in an office and part of my pushback is like one i i was like, first off, part of the reason I’ve worked so long remote is it is an accessibility thing for me like I do have you no learning things. Make it much more efficiently to you can ask my husband who works hybrid and he is very fortunate. He’s in media as an Editorial Manager goes to the office once a week, but you can ask him, I am sometimes a really annoying officemate. I am screaming and talking to myself. I’m I’m up and down. I take laps, but I’m stuck on something. I tap my pen. I have a loud keyboard. He’s like, I have a sound effect bar. I do play during meetings because I think it makes meetings more fun. Yeah, so if you’re just I’m also just a really annoying office meet. So

Cassidy Williams 48:03
I’ve learned about myself that I just talked to everybody. And I like it’s fun. I enjoy it. But I’ve realized, if you want me to get work done, you’re gonna want to let me work. From Home. talk your ear off if you love me.

Brian Rinaldi 48:18
So Aaron, you’re like, I’m advocating for me to work from home for you. Not for me.

Erin Mikail Staples 48:25
That’s exactly do you do you a favor? you a favor. Yeah. No, my husband’s like, wait, because I got no note. Like when I got upgraded my headphones from like, I got headphones from like a work stipend. And they mailed me noise cancelling headphones, just like those should have been from me. Don’t mean, you forget to charge your headphones half the time like those should have been mine. But yes, I’m very much I should work from home for everybody else’s sanity. But I mean, on that point, Cassidy like, you know, it’s, I’m a very social person, but I’m probably an ambivert. Like, I’m not as extroverted as many people.

Cassidy Williams 48:59
I’m an I’m an introvert that is outgoing.

Erin Mikail Staples 49:04
Yeah. So I’m an outgoing person, but like, I need to recharge like I need. And so if I’m really stressed about something, we’re not focusing on something. Everybody will know. Because like, I’m like, don’t talk to me, or I’ll get really quiet. And they’re like, and I’ve worked in an office before where they’re like, Are you Are you okay? Like, is something wrong? You’ve

Cassidy Williams 49:24
just got to like, shut up. I’m like, so that we can recharge again.

Erin Mikail Staples 49:28
Yeah, but it’s so interesting, but I know we’re kind of coming up here on Yeah, we’re

Brian Rinaldi 49:34
coming up on time. So we got we got two things we got to get to because Joshua asks, he came back…

Cassidy Williams 49:39
He came back. Hey, Josh.

Brian Rinaldi 49:42
He wants to know your favorite tech pun. And I know you do have a lot of those. Like always in the newsletter.

Cassidy Williams 49:49
I was going to say I love so many of them. It’s kind of hard. It’s hard for me to name a favorite. I think the first one that always comes to mind is just Spider Man is a web developer. It’s a classic. It’s It’s so good. Yeah.

Erin Mikail Staples 50:07
Yeah. And that’s it.

Brian Rinaldi 50:10
And then, okay, to finish. Well, we got it, we got to do our pick of fact or which I promised I would get like a graphic for like when we do pickle fact time, but like, That’s it,

Erin Mikail Staples 50:23
you just gotta tune in next time folks. Tune in next time, or maybe the time. Next time, or maybe the time after that, or maybe sometime in the future indefinitely. You have to go back to graphic or just me talking about, or someone else talking about.

Cassidy Williams 50:42
But all right, I have so many words about pickles. And I would love to bring the pickle fact today, if you don’t mind.

Brian Rinaldi 50:49
Yes, of course, please. Yes, please. So

Cassidy Williams 50:52
pickles are great. We all know this, of this is this is something that is actually a core fundamental thing of America that people might not know. Because even though pickles have been around forever since like 2000 BC or something like that. America was actually named after a pickle peddler, America, Vespucci? He was just like everybody should be eating pickles. It’s really good for like scurvy on chips and stuff like that. He was really selling pickles and pushing pickles all the time. And he came to the US and was just an error. He came to the US before it was even named, and they ended up naming the country after him. Like we’re America is named America because of America. Vespucci? This pickle peddler. And people just like Wait shouldn’t this be united states of Colombia but it was too late. And pickles are driving us

Brian Rinaldi 51:48
saying like it’s in our foundation with like, it’s a foundation core

Cassidy Williams 51:52
part of us as Americans because of America. Because of pickles.

Brian Rinaldi 51:59
I think that is an absolutely amazing pickle fact. And you’ve now ruined all pickle facts for the show going forward.

Erin Mikail Staples 52:07
Yeah, you’re like and the rest of all these pickle facts are gonna just be me frantically googling about pickles

Cassidy Williams 52:17
gherkins we trust.

Brian Rinaldi 52:21
Yep. You know, that’s what we saved this for the end. Because that’s what like, like, make this fit. Most people. Most people are just here for the people.

Erin Mikail Staples 52:28
Most people just come here for the pickle facts and maybe you learn something in the process.

Brian Rinaldi 52:33
Ever. I was like, Yeah, secondary to everything.

Erin Mikail Staples 52:36
I now want to be a Greek god pickles. Like I really relish this episode. I know we’re we’ve got to kind of kind of a big deal.

Cassidy Williams 52:49
This episode was a big deal.

Erin Mikail Staples 52:53
We had a you know, I feel like we got a good crunch into the world of what it takes to lead DevRel teams.

Brian Rinaldi 52:59
Yeah, I might have to just click and broadcast before

Erin Mikail Staples 53:06
like I’m trying to my brain it’s like trying to run fast of like, How can I come up with a pickle pun that has tech in it in the next three minutes.

Cassidy Williams 53:15
Well tech is our bread and butter. So

Erin Mikail Staples 53:19
it’s only natural

Brian Rinaldi 53:20
now you’re bringing up sweet pickles. And that’s really

Cassidy Williams 53:23
only like them on like really? Spicy chicken sandwiches sweet pickles on spicy chicken sandwiches. That’s that’s where they belong otherwise, no.

Erin Mikail Staples 53:32
So when people made we’ve discovered in the last episode before it so Brian reached out and was like, dude, like this thing with me. And we came with the idea of DEV relish. And then I never told Brian until our first episode live together that my pandemic hobby was tickling fermentation. So that was when everybody’s making sourdough. I was making weird pickled things in my cap. I cleaned I live in like New York’s got a tiny, tiny cupboard. And we only had like three closed cabinets. And I cleaned all of our pots and pans one week during the pandemic, because who needs them in a cabinet, too, because you have to keep on certain types of fermentation. You have to keep your jars dark and in a cabinet. And my husband is like, What the hell are you doing? You have three rows of pickle jars. And so now it is a thing and pickled asparagus is My Top Tier item. Oh, along with good. So good pickled asparagus and I make a fermented Bloody Mary mouth.

Cassidy Williams 54:33
Yeah, that sounds that sounds really really good. Maybe we’ll do one day.

Brian Rinaldi 54:40
I love I love pickled mushrooms. But anyway, now we’re getting so distracted.

Cassidy Williams 54:44
Anyway, thank you so much for having me.

Erin Mikail Staples 54:47
Thank you for baying for joining us.

Brian Rinaldi 54:50
Yeah, and yeah, so in Best Bets. I don’t know if you’re gonna be on fake not vacation. You’re gonna be gone. Ah work in the month is this public news or Yeah, you

Cassidy Williams 55:03
know I can be I’m pregnant. I’ve gone on Matt leave in like a month. So I might not maybe I’ll get really into pickles then but I will be a shill. If anybody wants to try contender for stuff. If you click the Yee ha button on our homepage that put you on the waitlist, or you can message me and we can get you a key a friends and family key because we’re still in early access, but you can try it out if

Brian Rinaldi 55:27
you want. Okay, I will be missing because it sounds awesome.

Erin Mikail Staples 55:30
I’m definitely going to be messaging you for that. So keep doing and we’ve dropped all the links today in the discord so if you’ve missed this or you are like me and you open the links, and then you close them later and you think that you’re gonna remember them. You could use Cassidy is really rad tool that she is shilling called raindrop or just join us on Discord and then add them to raindrop. But yeah, either or do both because that’s a good idea too.

Cassidy Williams 55:56
If it’s not written down, I will forget it. So. But anyway, thank you again. Okay, thank

Erin Mikail Staples 56:02
you so much for joining us.

Brian Rinaldi 56:04
Well, so for those who are still watching, we’ll be back in next month. We’ll get it scheduled soon and I will work on that pickle graphic, I promise.

Erin Mikail Staples 56:14
Thank you so much for the conversation and please keep in touch everyone. Bye