Giant Robots Smashing Into Other Giant Robots

436: Welcoming our new co-host Victoria Guido

August 18th, 2022

Victoria Guido is the new Associate Director of Business Development and DevOps Strategy at thoughtbot, and is joining Chad as co-host of the show!

Chad talks with Victoria about getting involved in DevOps work, transitioning to agile, moving away from her old community which was based on geography, and tips for people onboarding into a new role.

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CHAD: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Chad Pytel. And with me today is Victoria Guido, the new Associate Director of Business Development and DevOps Strategy at thoughtbot, and wait for it, the new co-host of this very podcast with me. Victoria, thank you for joining me on the show for this episode, for joining me at thoughtbot, and now for joining me as the co-host of the show.

VICTORIA: You're welcome. Thank you for having me.

CHAD: You do all of those things, right? [laughs]

VICTORIA: Yes, yes.

CHAD: So I'm hoping that we can introduce folks to you. I'm excited to have you on the show and for the audience to get to know you. Let's start with your role at thoughtbot. I think maybe you have the esteem of having the longest title at thoughtbot right now. [chuckles]

VICTORIA: Yes, I love it, Associate Director of Business Development and DevOps Strategy. So I'm not only doing business development but also planning our DevOps services and how we do that at thoughtbot.

CHAD: And you're on the Mission Control team, which for folks who follow along or want to go back and listen, we had Joe, who is the CTO of thoughtbot and the interim Managing Director of the Mission Control team, which is our new DevOps team and Site Reliability Engineering team, that's Episode 403. So I will link that in the show notes, but it's at as well. So, how did you get involved in DevOps work?

VICTORIA: Right. So I first went to my first DevOps meetup in 2017 when I was living in Washington, D.C. I had been working in IT and operations for about 5 or 10 years at that point. And I went to a DevOps meetup and met some really nice guys, and they were very...what I liked about it was that it was both the technology side and about culture.

And it was about how do we break down silos between different groups, and then bring in the automation and start to do next level type of operations? So that's how I started to get involved. And I started attending the meetups regularly and then became an organizer for the meetup and for the conference series. And that's when I became like the biggest DevOps person in D.C. probably. [laughs]

CHAD: Did you end up moving from the general IT work that you were doing into more DevOps focus work along that way?

VICTORIA: Yeah, at that time, that was when as a federal contractor, you know, agile had been around for quite a while. And I had been through several agile transformations with large program teams. And now DevOps was becoming more of a thing. And the project that I was on at the time was managing a large set of federal websites and was managing the build pipeline and process for how they got their code into the public's view and how they managed the servers and all the other back-end services that supported those applications.

So DevOps was both top of mind for the government. [laughs] They were trying to now be able to deploy as frequently as they were able to build new features. And it was part of the work that I was performing as well.

CHAD: You mentioned you were doing government work at the time. What was that like? What kind of work was it?

VICTORIA: Yeah, actually, my first job after college, my first full-time job, was at Citizenship and Immigration Services. And it was about a 200-person program. Some of the applications were actually written in Siebel. And so we had just a variety of different applications from Siebel to Java. And they had just transitioned to agile. And so that was taking a team that was managing Oracle releases and bringing them into a kanban style workflow and figuring out how do we be agile when we're in maintenance mode, and bring the team along with me?

And I worked my way up from a process engineer to project management and did a little bit of testing and a little bit of development in between. So it was interesting because it was a major transformational shift for that agency and still getting steeped in ITIL processes and how to do unit testing, acceptance testing, and all of those other kinds of critical processes for building applications. It was good.

CHAD: What does transitioning to agile mean when you talk about groups that size? You're talking about unit tests and that kind of thing, which can be part of agile, but I assume isn't the only aspect of it.

VICTORIA: Yeah, I think for that group, it was about changing the way we planned and managed work and figuring out what processes could we automate. So is there testing that we could automate or test data creation we could automate? And I think there are some concepts from agile that helped our planning, for example, making a physical board to manage which environments has which versions of Oracle in it.

Those types of concepts of just kind of stepping away from your computer and getting together with the group every day to talk about what issues they're running into that's kind of what it was. But there was still, of course, documentation requirements, big documentation requirements, and everything like that. So it was an interesting sort of half transition or tailored approach to doing agile with that type of team.

CHAD: And then from there, you moved into ongoing sort of consulting companies that worked with government.

VICTORIA: Yes, I worked for two pseudo-government financial organizations, Pension Benefit Guaranty Corporation and Fannie Mae, so my next two roles as a project manager and system engineer. So at Pension Benefit Guaranty Corporation, I got exposed to more system engineering and security engineering, working with their mobile device management policy, and actually designing the mobile device management to match DISA STIG. Sorry, I'm doing a lot of acronyms out here. [laughter] You can stop me if I use too many.

But that was really interesting and also upgrading their system, they were using to manage change for the organization so their ITIL services management tool. Going through the process of upgrading that project and coordinating across all the teams who delivered software at the agency was fascinating.

I went on to Fannie Mae, where I started to really build knowledge bases and start to build out actually using SharePoint at the time. [laughs] But figuring out ways to share knowledge across large teams and other large production support services teams, and how to get them collaborating so they could improve themselves and do continuous improvement, and learn what other groups are doing.

CHAD: That's one area where I honestly don't have a ton of experience. Most of my professional experience has been at thoughtbot or other smaller organizations. How do you manage that, or what are the big differences between large organizations like that and something at the thoughtbot size or smaller?

VICTORIA: The biggest difference between a large organization like that and a small one like thoughtbot would be I think of how change gets generated and started. In a small organization with a culture like thoughtbot, change can come from anywhere and very quickly have permeated the entire organization. With a larger organization, you can have leaders try to force change from the top down.

And you'll see individuals some will be 100% on board. Others will figure out how to qualify what they're already doing to fit that change. And some others will just be full-on resistance and just kind of be waiting for the next leader to come in so they can switch into whatever they were doing before.

And there is also that organic change that comes from individuals and then pushes up to the rest of the organization. But I think it's much harder, and you have to have a lot of will and a lot of support from leadership that they're accepting of those types of ideas.

CHAD: I think it's the nature of groups and companies to want to grow. Do you think that there's any way to preserve that smaller culture as an organization grows?

VICTORIA: I think so. I think it's possible if you integrate it into part of your core values, and that becomes a part of how you interview, and how you do performance reviews, and how you build your culture as a company. I think you can build it on those tenets.

I think in some organizations, there's usually some form of acquisition where you acquired a team from a contracting company, or you acquired a team of federal employees from another agency when you restructured. So it makes it a little bit more challenging to really integrate that part of your culture into every step, but it is possible. And you also have to accept that not everyone might be on board all the time.

CHAD: Well, I think that that is probably the biggest challenge is even in a larger organization, if you foster a culture where change can happen from anywhere, it's not necessarily top down. Transferring that knowledge or that practice throughout the whole organization is really difficult. Like if it's thousands or tens of thousands of people, adopting a change seems really difficult to me. So even if things are really organic coming from all levels of the company, you could end up in a scenario where everything is being done differently, everywhere.

VICTORIA: Yeah, and I think, too, when you're in a larger organization, there's more context for every unit. And so you can think this is a change we're going to do. This is going to be great. But then, once you actually see the way that people work, that change might not actually help them that much. And so I think that if people have autonomy to be able to make changes that make sense for them, that's more likely to be effective than if we tried to push change from the top down necessarily. And being in my position as a contractor, I really don't have authority to make a lot of changes.

CHAD: [chuckles] Right.

VICTORIA: So either I have someone backing me up, or I really get to know the individuals that I'm working with. And I can demonstrate and show them that there's a better way of doing it and do it in a way that gives it to them as an option so they can choose to adopt it. And that's usually the only option I have to give anyway, [laughs] so that's been effective because people do want to be better at their jobs or be more efficient. But a lot of times, I think the changes aren't really addressing their problem, and so it can be easy to push it aside.

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CHAD: So you mentioned you got involved in DevOps DC and then as an organizer. I know you also started to work with Women Who Code. Why did you get involved in the organization of DevOps DC and that kind of thing? Was there a business or a personal reason to do it?

VICTORIA: It was both. It made sense from a networking perspective, both in potential customers or clients and in recruiting. But also, I think it made sense. For me personally, the people who were showing up regularly were my kind of people, you know, [laughs] people who cared about blameless post mortems or feeling open or making me feel welcome when I came to the meetup. That was a big reason why I got involved. And it just made sense for me, too, because I was coming from an operations background. I'm like, oh, DevOps, this is the way that we're supposed to be doing things. [laughs]

CHAD: So you were really involved in the D.C. community and had been there for a while. But you recently moved to California.

VICTORIA: Yes, yeah. I've been in San Diego for almost two years, about a year and a half at this point. Yeah, big moves.

CHAD: What was it like to move away from your old community, which was so based on geography?

VICTORIA: Yeah, it was sad, but it was interesting how it worked out with the pandemic because when we found out we were going to move, was when everything shut down, and we went slowly remote anyways. And so I continued running DevOps DC remotely and some Women Who Code events for about a year afterwards.

And then, when I decided it was time to really shift away and actually be more present in the San Diego community, especially when the other meetups started going back to in-person meetups, that was actually really hard to say goodbye and to say that I wasn't going to be organizing anymore. And I really miss all my past organizers and people who would come to the events.

CHAD: Has it been difficult to form a new community locally given the pandemic?

VICTORIA: Yeah, I've looked at quite a few meetups. There are a number of good meetups here in San Diego, and LA has a great scene as well. But yeah, it's been hard for myself to just get out of the house and to find similar groups that have those same interests. That's been a challenge, but I think it's coming along, and we'll get there.

CHAD: And along the way, you joined thoughtbot. I'm curious, what were the things, in particular, that attracted you to the role or to thoughtbot? What were you looking for personally?

VICTORIA: Personally, I knew that business development was an area that fit my skill sets really well, and the things I like to do like going out, and networking, and talking to people. And this role, in particular with the DevOps strategy in there, really excited me because I could use all of these hours and hours I've spent in meetups and conferences to good use to help develop services within thoughtbot that are really tailored to our specific user groups and needs. And to work with highly skilled, highly regarded engineers and developers on developing these products I thought was really exciting.

And then thoughtbot as a company, in particular, I found the interview process to be really well thought out with, for example, I knew that it was going to be a long interview process. So there is a compensation that you can receive just for interviewing. And I thought that was something that was really nice [laughs] and also just showed that approach of being aware of the candidate's experience and wanting to have that be a good experience and a worthwhile endeavor. So that was part of why I liked thoughtbot.

Open source was a big consideration for me. I wanted to work somewhere where they were passionate about giving back to the open-source community, and all that together brought me here and made the most sense.

CHAD: Cool. Do you have any tips for people onboarding into a new role? Or maybe even if it's not tips, was there something that you did intentionally when day one or day minus one you're thinking about, okay, tomorrow I'm getting started? How did you approach that?

VICTORIA: One of the biggest advice I give to people who are starting a new role is to schedule one on ones with members of your team and get to know them as individuals, especially in remote environment since you don't necessarily have a chance to go out for coffee, [chuckles] just to have a quick one on one and get to know them a little bit more in your role and figure out where you can start to add value. I think that's a great way to start. And then to just develop your list of ideas for where you think you can add value, some outstanding questions for where you need to understand more.

And I think the other advice would be to engage in the social channels. I think my first day, I posted a picture of my dog on the dogs' channel. [laughter] And just like, let your personality show a little bit. And don't be afraid to post in a large channel, especially if you know the culture of the company is open to that kind of collaboration. And then people start to see your face and get to know you a little bit more, and you feel more connected to your company.

CHAD: Were you nervous when you joined on your first day?

VICTORIA: Yeah, a little nervous. And I'm also aware of just having been a federal contractor that some people might hear that and have an impression of my style or the way I like to work. And so I'm a little aware of like, oh, I definitely don't want to wear a blazer. I don't want to look too corporate.


CHAD: That's funny. Yeah, one time, we were meeting in sales meetings with clients, and we wanted to establish that we were not a typical consulting company. And so intentionally going to a sales meeting wearing a t-shirt or something like that was a statement, like an intentional choice we were making to subtly communicate what kind of company we are. So that resonates with me.

VICTORIA: Right. [laughs]

CHAD: So now that you've been here for...oh, geez, how long has it been? [chuckles]

VICTORIA: It's almost a month.

CHAD: Almost a month. Was there anything that surprised you?

VICTORIA: There have been a few small things that I'm probably way too happy about. One is just the actual page count in contracts is just way lower than what I've had to work with in the past, [laughter] which is very exciting for me. I was really happy to see...I went to go add a custom Slack emoji, and there were already like 2,000-plus Slack emojis. So that was really exciting for me. [laughs]

Surprising...the part that's interesting is, in some cases, as a consulting company, it is the same problems that we're trying to solve for. So, in that case, it's almost expected, but it's interesting. So to see some things like what thoughtbot has, a playbook in GitHub, and anyone can edit it. And that was something I was really trying to work on at my last position.

And you're 5 or 10 years down the road where you've solved some of the issues where you have a nice editor so that people can go in and edit pages without using Markdown or pull requests. But it's still difficult. So it's interesting to see that some challenges have progressed a little and have still some different issues.

CHAD: Yeah, it's always interesting to get a new person's perspective with fresh eyes. I've been doing this for a long time, and joining a new company remotely is different. Back when you were joining a Boston team or a San Francisco team, you could go into the office. And your first day, you'd be sitting right next to somebody and going to lunch with them. And that kind of thing is clearly very different now than it was then.

VICTORIA: Right. And I did get to see everyone at Summit for one night. So that's exciting.

CHAD: Yeah, that was exciting. So we happened to...I think the week before you started, or maybe two weeks before you started, we were having our company-wide in-person get-together in the United Kingdom. And you happened to be going to Germany for a wedding, right?


CHAD: So we tacked on to that trip and stole you for a day, and we were able to see each other in person. That was exciting.

VICTORIA: It was really cool. Although I had a lot of FOMO once, I saw the next day was like D&D and a bunch of games and hanging out. I was like, wow, I'd really like to stay longer. [laughs]

CHAD: Yeah, yeah. Well, we'll do it again next year. [laughs]

VICTORIA: Yeah, that's true.

CHAD: Mission control is the one team at thoughtbot that works on clients that is cross time zone, so most of the teams overlap with clients 100% with time zone. So it'll be people in the Americas work with clients in the Americas. But the Mission Control so that we could provide a wide swath of time zone coverage for that infrastructure work, for that support that we do, crosses the teams. So one person on your team is in Nigeria, and you're all the way in San Diego. What's that like? How do you manage that?

VICTORIA: Yes, well, everyone on the team makes sure to update their availability in their calendars so that we aren't accidentally scheduling meetings really late in the day for folks who are on that UK time zone. It's been all right, though. I'm used to asynchronous communication, and so is the team. So I think that we're really good at being able to use Jira and Confluence and Slack to communicate. And we are open with each other on where we're flexible if we need to make meetings a little bit later.

And everyone's been really supportive of not trying to have meetings too early with me, which I appreciate, [laughter] 8:00 o'clock is totally fine, though. It's actually been good. I'm used to the asynchronous communication. I actually would even be open to more meetings that are done just over Slack and just when people wake up.

CHAD: I think there are different philosophies here. But I'm very much in the camp of assuming we want to work a sustainable pace, which we do, then you can't build a culture around synchronous meetings where everyone needs to be on the meeting together because it's basically impossible. Those two things are at odds. Someone will be outside of their regular work hours, and that's really hard to continue on sustainably.

So I'm very much in the camp of having a culture of asynchronous communication. And that doesn't mean that you never talk. [laughs] It doesn't mean that you don't work with each other. But maybe those times should be focused on what can't be replicated asynchronously, which is sometimes the social connections, the cultural connections of the team.

VICTORIA: Yeah, and I think we get a kick out of saying like, "Good morning, Victoria, and good evening, Olamide." [laughs]

CHAD: Cool. Well, I'm sure folks will get to know you more over the course of the next episodes. I really appreciate you joining the show. If folks want to follow along with you or get in touch with you, where are the best places for them to do that?

VICTORIA: I'm more active on Twitter, and so you can follow me there. And I tend to like and retweet a bunch of DevOps-related events and Women Who Code events. And I'm also on LinkedIn.

CHAD: So what's that Twitter handle?

VICTORIA: It's @victori_ousg.

CHAD: Okay. We'll include a link to that in the show notes. You can subscribe to the show and find notes along with an entire transcript for this episode at If you have questions or comments, email us at And I'm so excited it's not just going to be me on that email list anymore. So definitely send an email. And you can find me on Twitter at @cpytel.

This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thanks so much for listening.

Victoria, thank you again.

VICTORIA: Thank you

CHAD: And see you next time.

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