Part 1 - Job searching as a software engineering bootcamp grad and persevering through layoffs

In part II we’ll cover Lisa’s overall career journey, her background in education, and how she transitioned to software engineering. For this post, we’ll focus on her job search process after her bootcamp with Flatiron. 

How did you feel when you graduated from Flatiron? How did you feel about starting your job search?

I felt good coming out. The boot camp was obviously very intensive, but I felt confident about what I’d learned and had been able to keep up with material.

And with complete transparency, I really didn’t have a lot of job-hunting experience at this point. My first job out of college, I was recruited by a former boss. I tutored student athletes and my boss joined an education startup and recruited me there. And even a lot of my freelance work, someone I’d worked with previously would reach out. I didn’t have much experience cold applying to jobs so I didn’t know what to expect.

My plan was to apply to jobs every day, while also to work on independent coding projects to keep my skills up and have something to show for the time. I wasn’t really doing any networking, just cold applying.

I didn’t hear back from anyone for the first 6 weeks which was really scary. Then things started to trickle in. I remember I had 3 interviews. My first one I didn’t make it past the first round. 

A technical interview?

Yeah, I think I passed the recruiter screen and failed the first technical interview. I basically thought I understood the concept of promises in JavaScript, but I only knew one specific syntax for it. The interviewer presented a promise in a different syntax than I was used to seeing and it exposed that oh, you don't really understand promises. You know how to get from A to Z in this one specific example, you can regurgitate the code to make it work, but you don’t know it deeply enough to apply it in a different context.

But that interviewer was so wonderful. We're still connected on LinkedIn. He was, I forget now, either a musician or a dancer in New York. He was also a career changer. And he’d founded this artists who code group that he let me join. It was a very positive way to totally blow my first technical interview.

I love that. People you meet in interviews can become connections even if you don’t get the job.

In the end after about 3 months of searching, which at the time felt unexpectedly long, I ended up with 2 offers. This was January 2022, and in retrospect the job market was quite good.

One offer was with PagerDuty for an internship that would turn into a full-time position if I did well. And the other role was a full time offer staying in EdTech.

While part of me wanted to keep the training wheels on and start with the internship, I took the leap for the full time position. I felt that would give my career trajectory a clear narrative and I’m truly passionate about education. So given the choice, I wanted to be in the education space.

The company built learning platforms for nonprofits, international NGOs, humanitarian organizations. And unfortunately, flash forward right now, they’ve had to lay off tons of people because so much of their funding came from USAID.

I got the job with them and it was a really small tech team: me, three other developers and our CTO and I was spoiled out of my mind at that job. Just had a wonderful team of people and just a really great company to work for. 

Ok, and spoiler alert, I know this story doesn’t end as happily as you’d like. What happened next?

I was there for about 1.5 years. And then September 2023, when all the tech layoffs were happening, I knew if we did layoffs too, it would probably be me because I was hired the most recently, had the least experience. I was definitely still in the learning curve phase.

We made it all the way to the end of September and I got my hopes up and thought we might come through unscathed, but of course then we had layoffs too. And I was let go.

What was your initial feeling?

I thought, I have work experience as a software engineer now. Before, I had to convince someone to take a chance on me with zero proof. Now I have this experience under my belt, it won’t be so bad.

Famous last words in today’s job market.

Ugh, I’m sorry. And how did you approach job search #2?

I still had no experience doing a concentrated job hunt. I wasn’t even using a spreadsheet to track where I had applied yet.

And then even once I started tracking where I had applied, I wasn’t keeping good notes. When I was doing the networking piece and reaching out to people, they’d ask “can you send me the job description?”

And I’d either have to spend a bunch of time trying to find it again and remember which role I’d applied to or it wouldn’t be online anymore. I was really naïve and it took me a couple of months to realize I needed to start doing this in a more professional way because it was going to be harder than my last search. I also found it a real struggle to know what to prioritize.

That’s a really good insight and I think very common. Tell me more about that.

I was looking for postings, and applying. I was studying for technical interviews. I would get a response from a recruiter and find out their tech stack was Ruby, so I’d pause everything and study Ruby like crazy. But then I wouldn’t get it and I’d get another technical interview at a different company and I’d switch to studying something totally different for that.

That’s surprising to me. In general, technical interviews let you pick the language you interview in, from at least a subset of 3-6. Many jobs are language agnostic on hiring, they care that you provably know how to code, but not that you’ve actually worked in a specific language before. There are exceptions to this at both the company and role level, but that’s been the norm in my experience.

Yeah, I do remember being offered a choice sometimes. I don’t recall if I wasn’t offered a choice or it didn’t occur to me to ask and I just assumed in this case.

I did always try to ask what the technical interview was going to be like. That's the biggest piece of advice I give people is, you can ask for more details. Just say, “Is there anything further you can share to help me focus my preparation?”

And I've had people say, sorry, I'm not going to tell you. But then I've also had people say, it's going to cover this or focus on this, and then I can go study that thing.

I definitely agree that many folks struggle to prioritize their time correctly. I’ve written about this some, about diagnosing where in the process you’re hitting a roadblock in order to better prioritize your time. Such as whether to prep for coding interviews (which usually come first in the tech screen) or whether to invest more time on system design (which are usually later in the full loop stage) but require their own different prep.

How were you deciding where to apply? Were you targeting a specific size or kind of company?

At first I was really picky. I wanted to stay in EdTech, to find a company that matched my values. As time went on, I was open to anything, a pay cut, absolutely anything.

So going back to the start, it was total radio silence for 3-4 months.

You were sending out applications and you weren’t getting recruiter screens or tech screens or anything back?

Yeah. It was an iterative process of oh, I need to be more organized. I need to be less picky. I need to be more systemic. I need to tweak my resume and cover letter.

Cold applying felt pointless.

It was a needle in a haystack. You have to find a company that’s hiring, a job that you’re qualified for, find someone you know there that can refer you, and then still pass all the interview hoops. 

My stress at this point was less around the interview process and more just actually getting in front of a human being.

I really resisted networking. The way it’s normally talked about feels really skeezy to me. And I didn’t want to post on LinkedIn all the time.

I’m curious about this advice to post on LinkedIn all the time. I don’t understand where this comes from.

Flatiron provides 3 sessions with a guidance counselor. And there are all these online networking groups and job-hunting webinars. People are just spamming. Putting fluff on their Instagram or LinkedIn. It’s just so icky to me and feels so pointless.

There was a girl on the webinar just spamming the chat going, “Connect with me on LinkedIn. Here’s my name. I’m looking for a job. Connect with me on LinkedIn.” Or doing that across lots of LinkedIn Groups.

Yeah, I think putting time into posting on LinkedIn when you’re job searching is close to pointless. There’re some exceptions we can talk about. But if you’re not a content creator, not trying to sell a subscription service, not working in Developer relations or an evangelist position, as someone hiring I’ve never looked at a candidates LinkedIn posts. I might skim their education and work history, but that’s only after they’ve already applied and are in the system. And if it did come up, it would probably only be in the context of a red flag. As someone hiring, I don’t have to time to go look at your profile.

The only jobs I’m aware of where your social media presence and social media following are directly relevant to your career are like you’re a Python representative of a Google Developer Relations and your actual job is to engage with people online. But for standard software engineering jobs, this advice really frustrates me. It tells people to spend time and energy on something that’s not valuable.

There is one way I felt it helped me.

Ooh, tell me more.

Posting on LinkedIn helped me tell every single person around me I was looking for a job.

And that was hard. First, I felt shame for being laid off even though I know I shouldn’t. And then I felt shame because it’s been so many months and I can’t get a job. And I just don’t want to talk about it. This is my current hardship, I want to escape from it, not talk about it to every single person I meet.

But it was effective—all these people were keeping their eyes open for me and sending me stuff. Some of it wasn’t relevant or what I do, but I was grateful they were looking out for me.

I also leveraged my writing background (I did curriculum development before coding) and so I wrote these stories on LinkedIn trying to highlight qualities I thought an employer would care about and things I was good at. Not here’s a problem I solved at work, but telling an anecdote to show how determined and persistent I am.

I don’t know if that directly had an impact, but it was something within my control that I could do.

I also went on other social media and asked people to connect with me on LinkedIn.

Were you also doing informational interviews or other 1:1 conversations?

Yeah, a lot of people didn’t know of open jobs but they knew someone who was a software engineer and they’d offer to connect me with them. I did a ton of information interviews that had no connection to trying to get a specific job. I would essentially just ask them about their job. What tools do you use? Do you study outside work? Do you have favorite podcasts that you learn from? Any books or other resources you recommend?

When you talked to people, did you ask them to suggest other people?

No, but I saw you mention that and I think that’s great. 

My analysis of what you did was that it’s not really about the LinkedIn posts the way people usually mean it. You’re very good at networking. You needed to expand your network, and you ended up doing it in a public way. I suspect you could have done that without the social media posts, just done it more 1:1 if that felt more comfortable. I don’t think there’s anything wrong with your approach, but I don’t think it’s the only way. 

You used your stories to get people to offer to connect you to other software engineers instead of going to them directly and asking do you know a software engineer? Can you introduce me?

I think the one benefit was I was able to cast my net wider faster. If I have a friend who’s a nurse, I wouldn’t necessarily have asked her for intros but now she’s sending me software engineering job postings that one of her friends posted. 

Yeah, that’s a great point. I suspect you could have put maybe 50% less effort into the posts for the same return, but it’s hard to say for sure. I think your approach is really clever. The follow through and informational interviews are more key than the social media posts themselves. But the posts opened up opportunities for that deeper networking.

How did things change once you started doing this? 

This is another place I got a lot of conflicting advice. I was hearing, you need to apply in the first 30 minutes or an hour after a job is posted, otherwise there’s 4,000 applicants and you’re not going to get seen.

But also you need to get a referral.

The internet says you’ll never get an interview if you don’t apply within 30 minutes of the job being posted. And also says you’ll never get an interview without a referral.

But then you can run into trouble asking for a referral if you’ve already applied.

Yeah, I think this is a great thing to unpack.

I’m confused about this advice to apply fast. The software doesn’t work that way. Recruiters and hiring managers use software to filter applications based on criteria such as education, years of experience, or key skills. It doesn’t matter who applies first. It’s not a first in first out queue.

And I’m sure it varies by companies, but often for referrals you need someone to apply via a referral link and if they’ve already applied you may or may not be able to give them a referral. 

Personally, I think referrals can be super helpful, though they have limitations. And the hurry up and apply advice seems totally baseless and unhelpful.

Another thing I tried was I created a video of a 5-minute HR-style interview. I put it on my resume, on LinkedIn.

Do you have any data or metrics from the video to help get a sense of how impactful it was?

I was pretty pumped the average view time was almost exactly half the video (2:25 for a 5-minute video), meaning I at least captured people's attention enough that they didn't immediately click away. My biggest goal was just to get attention, to just make someone spend more time looking at my application or to stand out in some way from other applicants, so I think it worked. 

Seeing the views it had per day, because I can see that it got more views during the times I was more aggressively applying for jobs, knowing it got seen, even for a few seconds, during those times implies my applications were actually getting looked at. I have no way of knowing if they would've gotten looked at without it, but it helps to know it wasn't all just tiny lost drops of water into the eternal empty void of an employer's market. 😂

Ok, I know you end up finding a job. Tell me how that worked out?

I reached out to a friend on LinkedIn who is also in the higher education management world and he said hey, I have these two job hunting groups in education. He puts me in these WhatsApp groups that I’m just silently watching, most of the posts aren’t a fit. But then finally someone posts one that’s up my alley except it wants 4 years of experience which I didn’t have at that point.

So I messaged the poster and asked if she thought they’d be open to considering someone with 2 years. I applied and got rejected. But later she saw another opportunity at her company that only asked for 2 years of experience and she reached out, asked if I was interested and if I wanted a referral link. And of course I said yes!

I applied, got an interview, and got the job.

Exciting!

Haha there’s more.

Oh dear.

I do all these panel interviews, so many hoops, it’s very stressful. After the final interview I get an email from the hiring manager saying he wants to talk.

He found out the company was going into a hiring freeze. They could only bring me on as a contract worker, but they’d try to convert me to full time as soon as the hiring freeze was lifted.

This was for a huge textbook publisher. I’ve been unemployed for 8 months. So, I take it.

I start in May and by fall, and I really appreciate him being so communicative and honest with me, we find out the freeze isn’t going to be lifted and contract workers will be laid off at the end of the year.

Oh jeez. I’m so sorry. Another job search.

The good news was I was able to slowly ease into the job hunt, but I definitely wasn’t fully recovered from the trauma of my previous search and was working full time, so it was hard.

The other good thing was that a lot of my network connections were still warm because I’d only been in this role for 6 months.

I started putting feelers back out, put the LinkedIn job alerts on, blah blah and got a couple interviews through networking.

But you DID find another job? You showed such incredible grit and resilience during this process. Tell me how the story ends (at least for now).

An old friend of mine from Baton Rouge had shared this job opportunity that his company was consulting for. It was a very vague job description. I reached out and said this looks right up my alley, do you know if they ever take remote workers?

He put in a hell of a referral for me. He said, guys this is your person. This is the person you need to hire. And anyway, long story short, I interviewed with them, made it through all the hoops, and that's where I am now. And it's actually been awesome.

Do you feel any less trauma now? There's no wrong answer. But if/when you decide to search again in the future, have you built confidence and muscles from this? I know it’s hard to predict how you’ll feel. But do feel any sense of empowerment from the tools and experiences of these 3 searches? 

So I would say for the job search itself, I would be totally equipped. I'd get my spreadsheets and my formulas and my data tracking. I think the interview process was more traumatizing. Being constantly evaluated, constantly having all of your insecurities and weaknesses on display, being treated like crap and people not treating you like a human being, so much ghosting.

I’m also nervous about how much harder technical interviews get, do they get even harder, as you advance in your career.

Did you do many system design interviews?

No, not really. More coding, algorithms, hey we have this bug can you figure out what’s causing it.

I don’t really think the interviews typically get that much harder. It’s a funny system because the interviews for entry level people are technically pretty similar, for algorithm/coding stuff, as more senior folks. The way they get “harder” is with system design interviews, but I honestly find many bootcamp grads excel in the system thinking, the conceptual, architectural pieces. Talking about putting a database here and a queueing service that can retry here.

Things you actually learn on the job.

Yeah, exactly. I’m sorry this experience was so traumatic. But I do think getting the data points of how different companies work, how they operate, their architecture, early in your career is really advantageous.

That’s nice to hear.

I think people level up way faster because they’ve seen tools before: oh I used graphQL at my first job. Or, oh ok I remember how we used Kafka at the other company and I see how you’re using it here slightly differently. I think the comparisons help people learn more than only seeing a single architecture.

Do you want to share any resource recommendations?

I mostly used Leetcode and some Udemy courses.

LinkedIn was probably my number one resource but I had to be really intentional and careful about it. Do I feel hopeless or did I just scroll too much on LinkedIn? 

Hahaha Oh man. That’s such a real quote. Am I really sad or did I just scroll LinkedIn?

Another recommendation, the traditional idea of networking always feels so cringe and sleazy so I always appreciate tips on how to humanize it. I can't remember if I'd mentioned it to you already, but when I was deep in my job hunting phase last year someone recommended a book to me called the Conscientious Connector. Honestly the kind of thing that probably could've been a long-form essay instead of an entire book, but I do recommend the concept, which is essentially to approach networking from a perspective of how can I help the person I'm meeting (the antithesis of how can YOU help ME or how can I get YOU to give me a REFERRAL). This mindset just makes networking something I can actually stomach.

Did you use your Flatiron bootcamp network at all?

Yeah, I reached out to folks from there. They also had a job portal specifically for companies that had agreed to partner with Flatiron, so I did use that.

Nice. I have found cold reach outs within an alumni network surprisingly useful. I might have gone to LinkedIn and searched “Flatiron software engineer” and looked at 2^nd and 3^rd connections to see what companies people were at, because it means they’re open to hiring from a bootcamp. I’ve also gotten a shockingly high response rates to cold emails with subjects like “<School> alumni reaching out.”

I’m so impressed with how you persevered and all the different tactics and approaches you tried including your stories and video. Your current employer is lucky to have you!