Caitlin cooke

Caitlin Cooke

Career Mentor Pathrise

Caitlin formerly led all things people at Nava and was GitHub's first recruiting leader. With her deep background in recruiting, she helps students and professionals land jobs in the tech space.


In this episode, we’re talking about getting hired with Caitlin Cooke, former VP of HR at Nava, and current Career Mentor at Pathrise. We get into the difference between getting hired in tech as opposed to other types of industries, the different steps to step up your interviewing, including creating a “behavioral matrix,” and the pipeline strategy of the job search process, including when to do cold emails and when to use a wide spread approach to send out your applications.

Show Notes


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[00:00:00] SY: Tickets are now available for our fourth annual Codeland Conference, taking place July 23rd and 24th in New York City. It’s the welcoming conference that brings together code, culture, and community, which promises to level up your software career. You’ll experience amazing talks and workshops led by an inspiring lineup of speakers. Early bird tickets and this week on February 26. Get them at See you in New York.

[00:00:34] Welcome to the CodeNewbie Podcast where we talk to people on their coding journey in hopes of helping you on yours. I’m your host Saron, and today we’re talking about getting hired with Caitlin Cooke, former VP of HR at Nava and current Career Mentor at Pathrise.

[00:00:50] CC: And it’s surprising, like even little things like changing whether your education’s at the top or the bottom can increase the response rate by like 50%.

[00:00:59] SY: Caitlin talks about the difference between getting hired in tech and getting hired in other industries, the different steps to take to step up you’re interviewing, and thinking like a recruiter to make a stronger resume and portfolio after this.

[00:01:20] Career Karma helps code newbies with free career coaching to help them learn to code and find a high-paying job in tech in less than a year. Download the Career Karma app to start your 21-day challenge and be one of the over 60,000 people who they’ve helped get started. Visit

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[00:02:46] SY: Thank you so much for being here.

[00:02:47] CC: Yeah, thanks for having me.

[00:02:49] SY: So tell us how you got started in recruiting and career coaching.

[00:02:54] CC: So I kicked off my career in recruiting with Disney actually. I was part of their college program back in the day, and I helped recruit students into the program and it just infused my love for recruiting. And from there, I basically built a career in university in college recruiting, and then went on to do industry recruiting at GitHub and eventually ended up leading the team there as well. And so I’ve just always been passionate about helping people find the right home for them. Now at Pathrise, I kind of do the reverse recruiting job of helping people find the best home for them in the tech space.

[00:03:33] SY: What is Pathrise? What do you all do there?

[00:03:35] CC: Yeah. So we are an online program for folks who are looking to break into the tech space. We provide one-on-one mentorship, training, advice, and we also have, it’s a 12-month program, but we have eight weeks of programming. So like basic concepts around like resume, what to look for, behavioral interviewing, negotiation, how to really understand under the hood what companies are evaluating you on and how to make sure that you’re reflecting that in your answers. And then we also have industry sessions throughout that as well. So for example, for software engineers, we have how to like tackle whiteboarding interviews, how to tackle algorithm questions. For designers, we talk about portfolios. For product managers, we talk about how to frame like product, whiteboarding interviews as well. So there’s kind of the two programmatic elements over the course of eight weeks. And then in addition, you get one-on-one mentoring from a career advisor like me or from an industry mentor as well who has been in the space in that field and worked at top tech companies as well who can really provide that expertise.

[00:04:40] SY: So you’ve done recruiting for a number of different companies. You mentioned Disney. You mentioned GitHub. You’ve also done it for Google, Accenture, Freddie Mac. In our world in coding, we kind of think of like the tech companies and then everyone else. I don’t know if that’s the healthiest way to look at it, but that’s kind of how we look at everything. So I’m wondering as a recruiter, as a career coach, what are the big differences between working with tech companies and working with non-tech companies?

[00:05:06] CC: It’s very, very different. My career did get started in the government consulting industry. So at Accenture staffing federal projects. It is very different in good and bad ways. Good way is there’s a lot of process behind how hiring is done, especially when you’re talking about government. It’s actually a legal thing for it to be done in a certain way, which actually creates a really great less bias process, I find, versus the tech space where it’s left up to the individual person to decide whether or not they like you based on what they’re hearing and whether or not you’re friends with them and then there’s a lot of…

[00:05:42] SY: It’s a little scary that way.

[00:05:44] CC: Yeah, it’s very uncertain. Oftentimes, not very fair. And so that’s kind of the main difference from a recruiting perspective. I think on the opposite spectrum, I think in the tech space, you have a lot more room for creativity. The interviews are very interesting and different. Sometimes it’s good, sometimes it’s bad. You can kind of play around with a lot more. It’s a lot less stringent. It allows for room to see maybe other qualities that people have that could be a really good value add to the role that whereas in a more traditional industry, they’re just kind of like, “Okay, do you meet this? Do you meet this? Do you meet this? Okay, we’re done.” Those are kind of the big differences I’ve seen.

[00:06:20] SY: So now you’re working in the tech space, you’re helping people get technical jobs. I’m wondering, do you have a technical background yourself?

[00:06:28] CC: I don’t. I’ve taken one and a half coding classes. I actually took a coding class in high school because I wanted to get out of math.

[00:06:39] SY: How did that work out? Was that the right decision?

[00:06:41] CC: Yes and no.

[00:06:42] SY: Okay.

[00:06:43] CC: I love video games and I was like, “I’m going to try it. I want to make video games.” And I was like, “Well, this is not for me.” But it was fun and it did give me exposure to the space. But no, my background, my degree is in, what is this? It’s actually defunct now, but it was essentially a humanities degree, but I’ve always recruited engineers for the most part. I never put it all over the spectrum, but mostly engineers, technical talent.

[00:07:07] SY: How has that been? Is it tough to recruit for a position where you don’t have a lot of experience in that role, in that industry?

[00:07:14] CC: Not really. I mean, a lot of it comes down to really understanding, like working with the hiring managers and the teams to really understand what’s important and what’s not important and why those things are important. And a lot of the times recruiters are keyed into understanding how people describe their projects in a way where they don’t have to understand the tech, like what’s under the hood technically, but they can spot, after experience they can start to spot like what is actually a deep experience and what isn’t. So that’s something that it just comes with time and practice and being able to really immerse yourself in what the teams are working on and why those skills are important. But that’s why companies have interview processes to have the teams evaluate from the skills perspective.

[00:07:56] SY: What is the demographic of people you mentor at Pathrise?

[00:08:01] CC: Honestly, it’s all over the place. A large portion of the fellows we help at Pathrise are new grads or bootcamp grads, but we do help a portion of fellows who are looking to transition into the tech space. Maybe they got their career started in a different industry or in a different type of role. They’re learning new skills and they’re really wanting to apply it either to software engineering, design, product management data. They’re all over the place and age as well.

[00:08:29] SY: So when you’re working with these different groups of people coming from different backgrounds or different goals, how does your coaching adjust to that? Are there kind of certain strategies you use for some people that doesn’t quite work for other people?

[00:08:43] CC: It’s not a one-size-fits-all. So the core eight weeks of the program, we do have programming around like how to do like software engineer interviews and whiteboarding and things like that. And so that’s pretty standard. But in terms of the one-on-one support that we give, it is very tailored to the individual. And so that involves really understanding their goals in their search and really understanding what they’re looking for, whether it’s a specific type of company. Even within the tech space, there’s different industries, different products. So really understanding that. Do they want something small or do they want something big? And all that information really helps us tailor a specific plan for them in terms of where they’re going to target with their pipeline, how they’re going to do that. So that’s really where it starts. And then it also translates to their resume, how they interview, how they get their stories across as well. So we help them every step of the way.

[00:09:30] SY: What’s the most common mistake that you see people make when they’re applying for jobs, specifically in the tech industry?

[00:09:37] CC: So that’s a really good question. So many mistakes. I’m just kidding.

[00:09:41] SY: Top three. Top three.

[00:09:42] CC: So I would say a lot of the time people come into Pathrise already exhausted from their search, and we work with them to really understand kind of how they’ve been approaching their search and what’s worked and what hasn’t. So in a way, it’s good because we have that data and we can work on it, but in another sense, a lot of the mistakes that we see people coming in, they kind of hit their head against the wall doing the same thing over and over again, either with the same resume or with the same approach. Maybe they look at LinkedIn every day and apply to 10 roles a day and they’re not really changing it up where they’re looking or how they’re reaching out to people or they lack reaching out to people. A lot of the fellows that we work with don’t necessarily have that. You’re not just born with the knowledge of how to network either. Some people are very lucky to have that skill, but most people don’t. And so that’s something we teach how that outreach really works for them and tailoring that as well.

[00:10:37] SY: So at Pathrise, I understand that you create something called a behavioral matrix.

[00:10:42] CC: Yes.

[00:10:44] SY: Interesting. What is that?

[00:10:46] CC: Yes. It’s not the actual matrix. I know, I wish. It is a really good framework to understand how to really frame your story in a way that gets across to interviewers and has them like kind of go through the checkboxes of what they’re looking for in a sense. A lot of the time people, they don’t really know what to talk about in the first place. And so they just start saying a bunch of things, like go on and on about something that the interviewer might not actually be looking for. And so we really help them carve it down to the most essential pieces of what they are evaluating them on, on the back end. And part of that involves mock interviewing. So we have each fellow write down their experiences based on like the top questions that we’ve collected data on throughout the industry. And we do mock interviews with them on it and we provide the interviewer’s perspective to them and say like, “Hey, here’s kind of where you lost me. Here’s where you could elaborate more on. Here’s where you need to elaborate less on.” And all these little minute details really help people perfect their answers in a way with practice and repetition as well to the point where they’re getting past those behavioral screens.

[00:11:55] SY: So after I do a behavioral matrix, what do I get at the end of the process? What do I walk away with?

[00:12:02] CC: Most fellows walk away with a sense of how to describe their story and who they are in a way that is the most relevant to the role they’re applying to. The other thing that the matrix does is really help people understand that the same answers shouldn’t be used each way the same time. Even if the question is exactly the same from company to company, sometimes the companies are looking for something different depending on their mission and their values. And so we really work with people one on one to help understand what those things are and to emphasize them throughout their interviews.

[00:12:39] SY: So what kinds of things do you ask to kind of get that whole thing started?

[00:12:43] CC: Yeah. So first, it depends on the fellow what they’re comfortable with, but we typically ask them to start writing down some of their experiences in a way where they’re very similar to the STAR format, sharing situation and context and results that are hitting the most relevant points to the role that they’re applying to. So we have them write it down in a digestible way, and sometimes depending on the fellow, we have them just write everything down and then we pair it down for them and tell them like, “Okay, here’s actually what we’re going to focus on. This is the most compelling or this is the most relevant.” And we break that down into pieces and then practicing it out loud so that they’re really comfortable sharing that experience or story in a way that translates to the role.

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[00:14:11] Career Karma is a free service started by bootcamp grads for bootcamp grads. Coaches, our current coding bootcamp students, who mentor people to help prepare and get accepted to bootcamps in just three weeks. We spoke to Kesha Lake who used Career Karma and is now an engineer at Stitch Fix.

[00:14:29] KL: I was really looking for a way to jumpstart my career, but not just getting me ready for the career itself, but to get me ready for bootcamp. I figured if I can do the 21-day challenge, then I can do the bootcamp.

[00:14:42] SY: So what was the challenge? What was it like?

[00:14:44] KL: The instructions were to speak to one person on your level and one person above your level every day and then post some sort of proof about it as a screenshot or a picture.

[00:14:54] SY: Did you know anything about coding before this?

[00:14:57] KL: I knew absolutely nothing about coding. So the 21-day challenge really set me up perfectly. I made friends, I started networking with people who would eventually make recommendations for me to get the job that I landed, but they also offered a lot of resources and support. You know, initially I was coding on my phone because I didn’t have a working laptop. Career Karma put me together with another one of their members who donated the first laptop and then I do get to upgrade to a Macbook so I’ve got another laptop from the Career Karma community.

[00:15:25] SY: So what kind of work do you do at Stitch Fix?

[00:15:27] KL: So I work on automation projects that help plan of ease the burden of our warehouse workers. So I kind of do a lot of telling machines what to do, which is exciting. It’s mostly back end work.

[00:15:35] SY: That’s fancy.

[00:15:37] KL: Yeah, it is. It’s kind of sexy and I’m really excited about it. I really leaned more towards back end development as opposed to front end doing bootcamp. So to find a job that would let me focus on that is kind of a dream come true.

[00:15:49] SY: Visit to get started. Let’s talk about resumes and portfolios. So I think for the most part, most people probably know what a resume is, right? It’s usually one sheet of paper that lists all your work experiences and has some bullets describing that experience. When we’re talking about nailing a tech job specifically, a technical role, what is the right way to approach and think about that resume?

[00:16:21] CC: With the resume, you often hear that the resume only gets looked at for like, what, 10 seconds, 30 seconds, something like that, which is actually very true from my perspective as a recruiter. The most important thing is funny enough getting the information across in the most concise and relevant way and formatted in a way that is clean and legible. So a lot of it actually has to do with the ordering of the resume and what story you’re trying to tell, which seems really weird because it’s like, “Well, why should it matter what order whether my education is at the top or the bottom or whether this project is here or there.” But it actually does matter because the recruiter is so used to seeing hundreds and hundreds of resumes and their brain starts to work in a way where they’re just really distilling down information in an order that they’re used to. And so we work with them to help them understand how the recruiter is reading their resume and what they’re getting from it. So things like dates are important. Sometimes we talk about project dates, if it makes sense to add them or not, because if they were so long ago, recruiters instantly kind of like throw the information away and they don’t even read it. So even just very minute details like that. So when we’re talking about the resume, it’s kind of like reading the mind of a recruiter and how they’re going to process the information. And it’s surprising, like even little things like changing whether your education’s at the top or the bottom can increase the response rate by like 50%. If you’re a new grad, you want to show that story immediately. You want to put that at the top. You want to show your degree, like you want to bold it if it’s related to the field. And if not, you want to deemphasize it, right? You want to hide, I hate to say it, but you want to hide it. You want to hide the things that aren’t as relevant or take them off completely. So there’s a lot of just my new things in there that you kind of have to play around with.

[00:18:17] SY: Yeah. I was helping a friend of mine review technical resumes actually, and there were two things that I remember from that that really stood out to me. The first is that a lot of people listed their GPA and their GPAs weren’t good.

[00:18:31] CC: Yes.

[00:18:32] SY: You know what I mean? I think there’s one that was like a 2.5 and I’m like, “Why did you tell me that? Don’t tell me that.” I thought that was just fascinating, this really common theme of just everyone putting, not everyone, but a good chunk of people putting down their GPA and not really thinking about, “But do I want people to know what my GPA is?” I thought that was interesting. And the other thing is I noticed a pattern where people who don’t have a lot of work experience will put their education up top. And so it created this pattern where if I saw education listed first, I assume you don’t have experience, like it kind of created like this pattern for me that I use the shorthand and I was like, “No, you have to read the whole thing anyway.” But it was just interesting how quickly I caught onto that and how it affected the way I was reviewing other resumes.

[00:19:19] CC: Yes. A hundred percent. Yeah, that’s exactly what I was talking about. Just little things like that it signals to the recruiter, they’re just matching, and this is human instinct, they’re like matching things in their head to what they’ve seen and they’re like, “Oh, new grad. Okay. Not experienced.”

[00:19:32] SY: Exactly. Yeah.

[00:19:32] CC: And they don’t even read the rest of the resume.

[00:19:34] SY: And it was within like an hour of reading. You know what I mean? Like I did not spend a lot of time all day reading resumes and very quickly I saw that pattern.

[00:19:42] CC: It sounds so insignificant, but we’ve seen such huge results come out of just those little tweaks that we make.

[00:19:49] SY: So let’s talk about portfolios now. As someone preparing their portfolio, especially someone who maybe isn’t very experienced, someone who just graduated from a bootcamp or a CS degree. What should I think about when putting my portfolio together?

[00:20:02] CC: Funny enough, a lot of people come into Pathrise not really wanting to showcase their projects or portfolio.

[00:20:10] SY: Why?

[00:20:12] CC: They’re hesitant. They feel like it’s not real experience, but it really is. They’re like, “Well, this was just a class project and everybody in my school had to do this. Therefore, it’s not important.” But that’s not true. A lot of the time people want to see what you’ve been working on, especially if folks haven’t been employed recently. They want to see what you’ve been doing in the meantime with your skillset and projects and portfolios are the best way to showcase that. And so we work with them to find ways to put it on their resume in a way that can explain the depth of what they’ve done technically. And so we use a lot of impact and quantification statements to highlight that as well. So it’s not just, “Oh, I developed different and then react.” It’s like, “Oh, like I developed a user sign in login page that can handle up to 5,000 registrations a minute or something.” And that doesn’t mean a metric. But you know what I mean.

[00:21:04] SY: Yeah. Absolutely.

[00:21:05] CC: We’re trying to showcase the depth of what they’ve built. And so a lot of it just boils down to that.

[00:21:10] SY: So when we’re putting together our portfolios and our resumes, especially for folks who are career changers, where they’ve done a lot of stuff, it just wasn’t technical. I imagine there’s a lot of decision making of what to include, what to leave out. What are some things that you suggest? This is a general rule of thumb that we might consider not putting in our resume or our portfolio.

[00:21:30] CC: Sadly, this is a very sad answer. But we do get folks who have a lot of amazing achievements throughout their career, not all of it translates to the tech space, or if it was a very long time ago, recruiters just generally find it sometimes wasted space. It totally depends on what it is, but we do have folks, for example, folks who have been graduating from college who still have like high school achievements on their resume. So I hate to downplay those things because those are great achievements, but it does signal like a lack of experience when a recruiter sees those kinds of things. From a more experienced perspective, looking at if you have a wealth of experience, you want to show the recruiter what the most relevant things are to what you’re applying to. And even if something is extremely impressive, sometimes you want to take that off in lieu of other things. I hate to say it, I don’t want to diminish the accomplishments people have, but sometimes the advice I give is to say like, “Look, you can love and cherish what you’ve done and be very proud of what you’ve accomplished, but you want to use that space to tell a different story right now.” And so sometimes we’ll recommend having the most recent project they’re working on in a bootcamp, for example, overshadow an achievement that they had 15 years ago. So sometimes it’s just about telling the right story and you can also keep it on the resume, but maybe not leave it up top or leave it up front. Maybe it’s something you can talk about in an interview as well. And so we find ways to do that.

[00:23:01] SY: What are some things that we want to make sure we do include in our resume or our portfolio?

[00:23:07] CC: Skills is a very interesting section that people tend to put in a lot of things like communication and organization and things that don’t, I don’t want to say they don’t have meaning, but on a resume they don’t, if that makes sense versus actual tools and technologies, especially in the tech space, making sure people are aware that you understand how Google Drive works, for example, which is a very common tool we use versus Microsoft is obviously given for many roles, but there’s little tools that are constantly being created and used in the tech space, Trello, Airtable, things like this that people don’t really think to highlight on their resume, but it really shows that they can adapt to new tools and have used newer tools in the space. So those are little things that sometimes we’ll point out or have people include to show that they are adapting to new tools. Sometimes things as simple as LinkedIn or GitHub links. Those are surprising, even though recruiters spend like 0.3 seconds looking at our resumes, sometimes they spend a lot of time looking at your LinkedIn.

[00:24:13] SY: They’re so easy to digest.

[00:24:14] CC: They are.

[00:24:15] SY: And they’re always the same format, they’re really predictable, they’re easy to scroll. It’s so nice to be able to just look at someone’s LinkedIn instead of the resume.

[00:24:23] CC: Yes. And I’ve known recruiters to only use LinkedIn like instead of the resume, like they’ll just download the PDF and be like, “This is the resume,” even though they have a resume, but a lot of people don’t realize that. And so we work with our fellows too to really understand, “Okay, what does your picture look like? How are you describing your titles? How are you describing your experience or yourself?” Or they have their LinkedIn on their resume and it hasn’t been updated in five years. And they’re like, “Well, I didn’t think it mattered,” but it’s the first thing they see on the resume. Recruiters love LinkedIn. So you want to make sure it looks good, but that’s the other thing I think that a lot of people miss too.

[00:25:03] SY: Coming up next, Caitlin talks about the pipeline strategy of the job search process, including when to do cold emails and when to use a widespread approach to send out your applications after this.

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[00:26:02] If there’s one thing that comes up over and over again in our podcast, it’s that everyone has a different way of learning. We had our producer, Levi Sharpe, try out Educative to level up his Python skills. And he really took to the service’s text-based courses with in-browser embedded coding environments. And Levi, what did you take?

[00:26:22] LS: I took learn Python from scratch, so I’ve been learning Python a little bit. So I was a little bit familiar, but I found that these courses, they’re laid out in a really intuitive way. There’s like these sections that lead seamlessly one into the other. The Python 1 goes from data types and variables to conditional statements, functions, loops, and then each section has a quiz to make sure that you’re not just blasting through and like the information is going in one ear and not the other.

[00:26:54] SY: I love the quizzes.

[00:26:55] LS: Yeah. It really called me out on my BS because I was like, “Yeah, yeah, I get it. I get it, I get it.” And then I took the quiz and they were like, “You don’t get it.” And I was like, “Ah!”

[00:27:05] SY: You got me.

[00:27:06] LS: You got me. And then throughout all of these different sort of sections, you can code within the service itself. So you don’t need like an external coding thing. I should know what that’s called. Do you know what that’s called?

[00:27:21] SY: I’m not going to tell you. I’m not going to give you an IDE.

[00:27:23] LS: Yes, that’s what it says, an IDE. Did you know I’m a producer for a coding podcast?

[00:27:30] SY: A technical podcast.

[00:27:31] LS: Yeah.

[00:27:32] SY: Two actually, two technical podcasts.

[00:27:33] LS: That’s true.

[00:27:35] SY: Get 10% off site wide by going to Okay. So we’ve got our behavioral matrix. We’ve got a solid resume. Our portfolio is in order. What are some things that we should consider when we’re finally starting to put ourselves out there and actually apply to jobs?

[00:28:00] CC: The main thing I really like to talk about after the profile, resume, LinkedIn, everything looks good, really understanding where people want to target and tailoring, we call it pipeline, but like a pipeline plan for them. So what we’re going to be doing goals wise each week and what we’re going to be targeting. So this is, again, like maybe like a little bit of a sad statistic, but even the best resumes and the best profiles I find in or outside of the program really only get return like requests for interviews about like maybe 10% of the time. That’s like a really good return rate is what I usually see.

[00:28:38] SY: It’s really validating though.

[00:28:39] CC: Yeah.

[00:28:40] SY: For all of us out there who just like never hear back, that feels good. Thank you for that.

[00:28:44] CC: Yeah, that’s good. Yeah, exactly. Like the most experienced like fellow I’ve worked with got like callbacks maybe 10% to 15% of the time. For most people, it’s a really good number to have like some around five, that’s about average, 5% to 10% really good. So anyway, after we’ve worked on the resume and the profile, we really work on how we’re going to target the pipeline. And depending on what people want, we think about if doing a more personal reach out is going to make sense. For example, the game industry, that’s an industry that’s very difficult to get into, especially if you’re entry level. And that’s something that we work with folks on in terms of targeting like who in the industry are we going to reach out to. Maybe we think about Twitter, like as a tool, that’s a big place for folks in that industry kind of live and talk about. So we talk about those things. It’s not just about, “Oh, Epic has a role. Let’s apply to it.” There’s a lot that goes behind that. We also think about techniques. We have a technique called mail-merge, which is like the opposite of what I just described. Instead of it being more tailored and figuring out who to reach out to individually and writing a very personalized email that gets across all these amazing skills and passions in the gaming industry, we’re doing the complete opposite and sending our resume to hundreds of companies in the area you live into small companies that may not have a lot of competition, they may be really excited to hear from somebody looking to be a designer or a software engineer. And so we utilize tools like that as well to really get the pipeline flowing. And a lot of that is around setting goals and dedicating the time to doing it because it is a lot of hard work, but that’s kind of the next step is making sure that that’s running and the interviews start to come in and then we do the hard work of the behavioral matrix and the prep around that and the mock interviewing and the industry mentor prep as well in terms of mock interviewing.

[00:30:36] SY: So when we talk about literally applying, hitting that submit button, there are so many different ways we can do that. We can apply through a form online. We can send a cold email or a warm email. We can go through the one-click submit platforms that they have where you just click and you’d automatically submit your information. There are so many different ways that we can do it, but I assume that the best way is a warm email. Is that right?

[00:31:00] CC: Yes. So if you know anybody anywhere, that’s always the plus, the number one thing…

[00:31:07] SY: Anybody anywhere.

[00:31:08] CC: Exactly. Like literally you know anybody who works at the company or maybe you don’t know them, but you know somebody who knows them or you maybe saw them at a conference, any connections, slight connection that you have to a person at the company you want to work at is always going to be your best bet over emailing like a random person or just submitting the application. That’s usually our first go to. So for folks who are really looking, for example, we have fellows who are really interested in like the top Amazon, Google, Twitter, et cetera and we really work with them to understand, “Okay, like who’s in the network that we can tap into?” We might have people in our network as well that we can tap into. And we really try to curate that in a way where we can get folks like their foot in the door, essentially. Back to your point around applications, there is one thing that we recommend people don’t do, and that is don’t click that easy apply button. It’s a black hole.

[00:32:04] SY: Interesting. Oh, tell me about that.

[00:32:07] CC: LinkedIn, Glassdoor, Indeed, all of these different aggregators and sites usually have their own portal that hosts the resumes and applications that they submit. Not always, but a lot of the times they do or the recruiters can choose to do that and it doesn’t always populate in the company’s tracking system, the ATS, the Applicant Tracking System, and that’s typically the source of truth that recruiters use to filter through the applications. So what ends up happening is when you click the easy apply and it says, “Okay, like you applied through LinkedIn. Great. You’re done.” Sometimes the recruiter doesn’t look at LinkedIn every day or their applications every day. Sometimes they’re in there once a week, maybe once a month, and they’re in their ATS every single day. So you really want to send the application straight into the company, and a company with a cold email if you can.

[00:32:56] SY: Let’s go back to those warm emails, and you mentioned, “If you know anyone at all, anywhere, reach out to them.” What do you do when you reach out to them? Are you asking for an introduction or are you asking for recommendation? Which it feels kind of aggressive, I guess. What is the ask for these warm emails?

[00:33:13] CC: It’s definitely a hurdle for some folks. It does seem really intrusive, but it actually does have to be aggressive for it to work. And the easiest ask is really something that’s straightforward, simple to do. Oftentimes we recommend that through either specific times, like, “Hey, are you free to chat tomorrow between this and this?” Very easy, like it’s a yes or no question. Or like, “Here’s my Calendly link. Book some time.” So that’s like a very easy thing to do. Or, “Hey, like I work right down the street. Do you want to meet at this coffee shop this week?” Like very simple, straightforward, ask that isn’t complicated or too vague or ambiguous for the person to really respond back with. So the ask can be many things, I guess, to answer your question, but the important thing is that it is specific and easy for them to respond back to.

[00:34:01] SY: But in terms of applying for the job, is the ultimate ask a recommendation or a referral?

[00:34:07] CC: It could be either. So we do teach folks to ask for informational interviews because sometimes that can open up the door, especially if there isn’t a role that is open that they’re interested in. So if somebody comes in wanting to work at a specific company, for example, but that company doesn’t have any open roles that are catering to that person’s background, the ask will be, “Okay, well let’s do an informational interview to get to know more about the company,” and that could lead to, “Oh, well, this person seems great. Maybe we’ll open a role for them.” So that’s happened before. But if the company does have a role posted, the ask is typically, “Is it possible to move forward or is it possible to talk to somebody on the team or something of that nature?”

[00:34:48] SY: And is that kind of industry standard? Like is that something that the other person should reasonably expect or is it a strange request?

[00:34:57] CC: No, absolutely not. As a recruiter, recruiters get these requests all the time because that’s their job, obviously, is to hire people. So you are obviously going to reach out to them, but something that we teach folks to pay attention to is not just to reach out to the recruiters, but do some reverse recruiting and figure out who the hiring manager is. So we teach people how to do that on LinkedIn, how to search for people and identify keywords in people’s profiles to understand, “Could this person be managing the team that I want to be on? And if so, maybe I should reach out.”

[00:35:26] SY: So this pipeline strategy, does it change depending on whether I’m looking for a big company, a small company, a junior role, a senior role? Do those things factor into how I might approach this pipeline stage?

[00:35:41] CC: Yes. So it is in a sense, when searching, obviously the right keywords matter within that, depending on how specific their searches, the advice gets a little bit more specific. So we might talk about doing Boolean searches instead of just looking through Glassdoor or LinkedIn.

[00:36:00] SY: Oh, what’s a Boolean search?

[00:36:02] CC: So Boolean is basically a very targeted keyword search through Google. It sounds fancy and it can be very fancy. It’s tricky because basically you’re manipulating Google to spit results back out at you based on how you answer keywords. And so using like “and” or using quotations, parentheses. So it’s like making sure that you are grouping the right keywords in a way that’s getting the results that you want to see.

[00:36:35] SY: And does this strategy depend on the size of the company that you want to work for?

[00:36:40] CC: Size is important when it comes to the reach-outs. So obviously writing a bunch of cold emails to recruiters at Google, probably not going to be super effective. Writing some cold emails to a small startup in your hometown that you live in, probably very effective. When you’re talking about the size of the company, it comes down to reaching out to the right people, especially the smaller the better. And that’s really where our techniques around mail-merge are really useful because we’re targeting smaller companies, typically less than 200, maybe 100 people where they’re really not getting spammed with a lot of emails. And maybe they’re not as competitive as other smaller startups. And so they’re happy to see emails from people. And we really use it to utilize that if people are looking for smaller companies to kind of get the resume out to them. With larger companies, again, it’s about networking in terms of knowing who you know or who you know who might know somebody. And so utilizing that and understanding how to send those reach-outs is really where we target.

[00:37:48] SY: So from the day that I say, “Okay, I am going to get a job, I want to get a job in tech, in a technical role.” As soon as I can, what is the average amount of time I should expect that to take? If I know that right now I’m going to start, I’m going to get to work, I’m going to start on my resume, do my behavioral matrix, whatever that is, how long should I expect it to take me?

[00:38:10] CC: It really depends. I will say that most folks that we place the average is around I think three to six months.

[00:38:20] SY: Okay.

[00:38:21] CC: But I have seen it very quickly and I have seen it also take nine, twelve months. It depends on how open folks are in their search. That’s one major factor. So people who are, “I don’t care where I am, as long as I’m working for a cool tech company somewhere in the United States,” probably going to get placed very soon. Somebody who, for example, lives in Chicago only wants to stay in Chicago, only is interested in large companies might take a little bit longer.

[00:38:50] SY: Yeah. That makes sense.

[00:38:51] CC: Yeah. But that’s about the averages. It’s usually about three to six months.

[00:38:59] SY: Now at the end of every episode, we ask our guests to fill in the blanks of some very important questions. Caitlin, are you ready to fill in the blanks?

[00:39:08] CC: Yeah, absolutely.

[00:39:09] SY: Number one, worst advice I’ve ever received is?

[00:39:13] CC: So actually this relates to what I’m doing now. So my first job out of college was at Freddie Mac, and I was at the time the economy, I was in a slump. There were no recruiting jobs. I thankfully found a job in IT Project Management.

[00:39:29] SY: Nice.

[00:39:30] CC: But I knew I always wanted to go back into recruiting. That was where my heart was. And at the time I had some mentors at the company tell me, “Don’t do it. The economy’s going to crash again. IT is where the money’s at. You’re never going to make any money in HR. You’re never going to be happy.” I think three people told me this and my parents included. And I was like, “Nope. I love helping people. I knew I wanted to do this.” And I left. I left that job and I found a job. And they were right. I didn’t get paid as much at first, but I was so much happier. It was, honestly, the best decision I ever made is to not stay in old IT.

[00:40:09] SY: Wonderful. Number two, best advice I’ve ever received is?

[00:40:14] CC: I’m going to butcher this saying, if you love what you do, you’ll never work another day in your life.

[00:40:19] SY: That’s pretty good.

[00:40:20] CC: Did I say that the right way? Yeah.

[00:40:21] SY: I think so. That’s what I know anyway.

[00:40:23] CC: Yeah, but it’s true. Obviously not every job is perfect, but if you love most of what you do and you love the people you work with and you’re not being dragged down or bogged down with the work that you don’t like, it truly is a blessing and it’s something that kind of ties back to the last question. I’m so glad that I didn’t stay in IT just to sit there and retire with a pension or whatnot. I say that to my fellows all the time. Sometimes they struggle and they think about, “Well, maybe I should just give up and kind of go back to what I was doing.” And I’m like, “No. You can do this. And so many people before you have done it and it takes time, but you hang in there.” It’s so rewarding to love what you do and to get paid for it.

[00:41:14] SY: Absolutely. Number three, my first coding project was about?

[00:41:18] CC: Okay. So in high school, in my coding class, the way they taught us how to code was, I don’t know if anybody else, every time I’ve ever talked about this, nobody’s ever heard of what I’ve talked about, it’s called Carroll the Robot.

[00:41:32] SY: Oh.

[00:41:32] CC: And she was this robot we had to program in Java to navigate this maze.

[00:41:37] SY: A physical robot, like 3D robot?

[00:41:39] CC: No, she was just on our…

[00:41:41] SY: In the computer?

[00:41:42] CC: Yeah, just in our computer. And she was just struggling through this maze and we had to code her. It was directional coding. The very first thing we had to learn how to do was to navigate her out of the maze. But to this day like when I talk about this, nobody’s ever heard of it. This was like in 2002 or something or 2000. So I don’t know.

[00:42:02] SY: Number four, one thing I wish I knew when I first started to code is?

[00:42:07] CC: Like I said, I came into coding. I was like, “I wanted to get out of math. I didn’t realize coding was harder than math at the time.” In my mind, I’m like, “Video games! Great. I love video games. This is going to work out perfectly.” And I’m like, “Oh my gosh! What did I get myself into?” But I mean, I learned it eventually by the end of the class and my teacher was amazing. I was one I think one out of two women in the class and he was like, “Please stay. Please. I know you can do this.” And I’m like, “No!” I know.

[00:42:39] SY: Okay. It’s like, “No, thanks.”

[00:42:40] CC: I know. But looking back, I appreciate that a lot because somewhere between 2000 and 2002 my memory is awful, but it was so long ago. And looking back, especially now where the tech space is at, I’m like, “Oh, I really appreciate him for that,” but I wish I had known coming in how hard it was going to be, but some people aren’t built for it and I’m one of them.

[00:42:59] SY: So it’s interesting because you just said some people aren’t built for it, and I guess I wasn’t one of them, which is very interesting to me because I think that there’s a lot of doubt that people have to deal with in the job application process where it gets really hard. They don’t have any interviews. It’s been a long time and they start to think like, “Maybe this isn’t for me. Maybe I’m just not good enough.” How do you deal with that? Is that a voice that we just have to be strong and just ignore or is there a point when maybe you should stop? Or how do you navigate that?

[00:43:30] CC: Yeah, that’s a great question. I mean in my example, personally, there are things that you do and you know you find no enjoyment out of it and that you find that out pretty quickly, right? But most people don’t go through an entire bootcamp or entire four years. You know what I mean. But in terms of the search and the struggle, I have still to this day never worked with somebody who wasn’t talented in what they chose to do. If you dedicate that amount of time and energy into learning something new and you like doing it, you’re probably good at it. It’s very, very likely you’re good at it and somebody will pay you to do that for them. Sometimes we do talk about pivots. So maybe something related that’s not quite what they were looking for at first, like for example, some folks come in very strongly, “I really want to do full stack. I want to do everything. I don’t just want to do frontend or backend,” and sometimes we find that, well, they can actually still do those things in a frontend role or like a traditional backend role and learning about really this. So really like pivoting the way they think about the surge versus like I must have this and then thinking about, “Well, every company’s different,” and they think about their roles differently and how each team member has a play in that. And so we think about that in terms of support engineering as well or infrastructure. There’s a lot of roles that are very similar to what the ideal role is and there are still ways to contribute in that way that companies might be more willing to hire. That’s a piece of advice that I would give to folks is to be open minded about the types of roles you’re considering.

[00:45:04] SY: Well, thank you so much for joining us, Caitlin.

[00:45:06] CC: Yeah, of course. Thanks for having me.

[00:45:15] SY: This episode was edited and mixed by Levi Sharpe. You can reach out to us on Twitter at CodeNewbies or send me an email, Join us for our weekly Twitter chats. We’ve got our Wednesday chats at 9 P.M. Eastern Time and our weekly coding check-in every Sunday at 2 P.M. Eastern Time. For more info on the podcast, check out Thanks for listening. See you next week.

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