Finding a New Infosec Job - Part 2 - The Thinkening

Finding a New Infosec Job - Part 2 - The Thinkening

Finding a New Infosec Job - Part 2 - The Thinkening

Where I Was Mentally Through All This

I don’t know how to format this, but I feel like it would be good to just open up and say where I was mentally through this process so if you’re feeling some of the things I did, maybe you’ll know they’re normal. This will be a very fuzzy feelings oriented post because that was a lot of this process for me.

I won’t go into specific nitty gritty details about what was going on at my job, but suffice to say, I leave with very positive feelings towards the company and my team, despite the challenges we faced. I have a lot of respect for the work we did and the work we were trying to do and if I was in a situation where changing jobs wasn’t an option, I could probably have been there longer. I’m sad to leave a lot of the people I’ve built a strong relationship with and I’m sad to leave a company I have put 4 years of my work into to improve what I could. It sucks, but it is what it is and hopefully I can spend the next 4 or more years building cool stuff somewhere else with a team I respect as much as the team I’m leaving.

Before Deciding to Apply

I was feeling anxious. I knew my current role wasn’t working out. I was getting great reviews, bonuses, and recognition from peers and management, but I wasn’t happy. I had set out to focus nearly exclusively on engineering detections and as my situation changed at work, I was being pulled away from that work, having less and less time to do what made me happy. It was frustrating because I wasn’t satisifed with what I was doing but all the external signals I was getting were very positive and that clashed pretty sharply with what I was feeling internally. On top of that, I have a pretty good idea that my situation wouldn’t change at least for the next several quarters, maybe less, maybe more, but certainly not very soon.

Also, I had been at my previous role for about 4 years. I didn’t have a specific stock vesting schedule or anything (these began vesting at year 3 for me, I got 2 payouts from that process) I was considering because of how compensation worked (non-salary compensation was already being paid out yearly), but 4 years is a long time considering the average tech role lasts 2 yearsish (maybe that’s changed since I last looked it up).

I hate changing jobs. Applying is stressful, the unknown is stressful, leaving people behind is stressful, making new friends and teammates is stressful, all of it is uncomfortable. I don’t know any way to deal with that except throwing myself into it and it felt like after 4 years with things the way they were at my current role, all signs were pointing to it being time to start looking for somewhere new.

Applying for Roles

I was kind of resigned that I was leaving the company I spent the last 4+ years at. It was a difficult decision because I really liked the team I worked with, I had a great relationship with my manager, and we had onboarded some new people I had very good feelings about. Deciding it was time to leave was hard, but once that decision was made, it was time to go through the practical steps to make that happen.

That meant

  • updating my resume
  • scoping out potential companies
  • having an internal dialogue practicing interview questions
  • framing my story (more on this in another post)
  • sending out applications
  • fielding responses
  • scheduling calls and meetings
  • interview prep as necessary
  • and on and on and on

All recruiters moved at different speeds. I was up front with every company I applied to that I was applying to a few different places and kept them updated where I was to encourage them to move their process forward. This worked out in my favor in that some interviews moved very quickly, but others moved entirely at their own pace (about a week between “The call went great, we’ll follow up” and the actual follow up to schedule the meeting with 2 companies) regardless of my schedule or how quickly I turned around requests.

This can be frustrating and probably would have been if I wasn’t juggling so many processes at once. It meant I had no time to really get down about how a process was going or get too excited about anything because I was always fielding something else at some other part of the process. It also meant as I learned things about companies I’d interview at or discovered new questions to ask, I could ask them of new companies as I went through their process.

For example, early on, I knew that people leaving the team was something I was interested in knowing about. Would I be joining a company where all the institutional undocumented knowledge was gone? Were they ready for that if it happened? As the procecss went on, however, I became particularly impressed with how some companies handled work life balance and I began to ask more questions about that as my interviews went on. Work/Life balance was always important to me, but knowing how some companies handled it and how some knew the balance was off and required more people to fix was an important thing to look for as I continued my search.

During the Interview Process

Being involved in so many interviews meant I had to be ON TOP of things. I was balancing an enormously difficult schedule of a full time job, personal and family life, and interviews with several companies. I had projects I was completing, zoom calls with recruiters sandwiched between work meetings, skipped lunches, late nights, long days, early mornings, and anything else to get through this process. To help minimize the impact of being so multi threaded, I completed tasks as they were queued up. For example, I was given a week to complete a take home project as part of an interview process and turned it around that same night it was assigned.

This is a good example of some of the privilege I know I have that helped me through this process. I have a stable family life, a supportive partner and healthy kids, a stable job and steady source of income, flexibility in my work schedule, the ability to work from home, and all sorts of other things that made this marathon possible. Someone else I know who landed a great job around the time I was applying has their own set of circumstances and took 6 months from when they started interviewing to when they landed a role and we likely went about this process very differently.

There is no wrong way to do it, but there is a wrong way to do it for you. I think if I go through this process again, I’ll apply to one or two roles at a time to avoid serious overlap between my schedule. It was very stressful and I didn’t lean on a personal network much, I probably could have done that more.

When You Get Rejected

I completed the interview process and got rejected from one role where I did not apply but a recruiter reached out to me to start the process. For this company, I had 2 calls with a recruiter, a call with the manager, a take home project, a final all day interview (4 technical sections and a manager call), and then got decision back pretty quickly.

Among the things I liked were that the team and manager seemed incredible. It was a Senior level role, but I felt like I might be a junior amongst seniors and have a huge opportunity to learn from the people around me and really leapfrog in my skills. The company is modern, the environment seemed extremely complex and interesting, and I would have an opportunity to focus on what I was good at as I earned new skills and took on more responsibilities.

The interview felt like it went really well and really poorly at different parts. I felt like I had asked a lot of questions before the all day interview about whether they really thought I’d be a good fit, what exactly they were hiring for that made me a good fit, and I came to feel that despite my weaknesses in some areas, I would possibly be qualified based off the needs they had for the team. During the all day interview, I felt like one section on architecture went well, one section on software development went poorly, and the other security focused sections went pretty well, so maybe I did well in 3 out of 4.

Hearing I didn’t get an offer was pretty disappointing. Even though I knew it was going to happen a few times through all of this, it still sucked when I heard it. Additionally, there was not feedback on why I was not given an offer, simply that “it was close” but ultimately they decided against me.

My first reaction was frustration at how long I spent on the take home project only to get rejected. I was also frustrated that I would not get an understanding of why I didn’t get the role and wouldn’t know what to learn or focus on to improve. Finally, I was frustrated at myself for feeling like maybe I was qualified but didn’t show it during the interview or failing to prepare well enough.

Those aren’t productive feelings especially when I had quite a few other companies to interview with. I let myself be down about it for a little bit because that is fine and normal, but knew I shouldn’t let it influence my views of the people that interviewed me or the process I went through. It’s important to know you don’t always have the best understanding of how you appear to others, you don’t know exactly what red flags someone else is looking for and how you display them, and sometimes things just don’t work out.

At the end of it all, I came to the conclusion I would not try to interview with that company again, primarily because of the lack of feedback, but I did end up with respect for the people I interviewed with and no negative feelings towards them or the company. Everyone I spoke to seemed extremely skilled in their particular focus area, all of them handled me professionally and respectfully, and their process seemed about as fair as a technical interview could be. Maybe that contributed to how much it hurt to not get an offer, but that’s just what it is sometimes.

Processing All of This After the Fact

If I were to come out with any specific bits of advice for anyone going through this process, you should understand what you are looking for, expect to get rejected at least some of the time, and be ready to reject an employer that doesn’t feel right for you. If you’re privileged enough to not need to accept the first job you are offered, understand that an employer may offer you a role that’s not in your best interests or that you are a better match for them than they are to you.

Sometimes its explicit and the expectation is set early you’ll be working an unreasonable schedule or doing work you don’t find fulfilling. Sometimes its less obvious and just a gut feeling you and the manager won’t “click” or answers to some questions hint at some place you might not be happy. Being willing to turn an offer down with the expectation you will have another one coming from somewhere is empowering, it lets you choose the direction for your career and find a place you can feel fulfilled and really deliver meaningful work for your employer.

Getting rejected could mean anything from you were not qualified for the job, you were qualified but didn’t show it, you were qualified and they didn’t see it, or any other possible reason. It’s not personal, its not a reflection on your worth as a person, and you’re going to find something.

This all goes in the other direction too. Leaving your company doesn’t mean its a bad place to work, it doesn’t mean you don’t like or respect your coworkers, and you’re not letting anyone down. Sometimes coworkers are a big part of your life and it sucks to go somewhere else, but that’s just part of this process.

Closing Thoughts

I have a lot of optimism for what I will be doing and the people I will be working with. I’m excited about having a new team, working on new problems, sharing what I know, and learning from people I’ve never worked with. I also feel the weight of impostor syndrome so heavily so I am a bit scared I don’t know anything about anything and won’t be able to contribute and might get fired in 3 weeks. I’m worried the things I know aren’t really that interesting and I won’t live up to expectations the team and my manager have for me.

As I begin my remote onboarding process, I see tools and processes this new company is using that I have experience with, that I’ve seen the rough edges behind and I’m excited to see where I can help. I think back to the interviews I had with my future team members and think about how I feel like we clicked, how we discussed problems we’ve both tackled in similar and different ways and am excited to put all that stuff together. I feel a lot of things and that’s overwhelming sometimes but its also very exciting and I hope if you go through this process you’re equally excited about coming out the other end of it.