My recent job search by the numbers

By | May 27, 2023

Now that my job search is over, it’s worth doing a by-the-numbers look back at my search. I don’t think we talk about this stuff openly enough, and I hope that sharing my experience will help other people to understand that they’re not alone in finding it tough to land a job.

Before I break down the numbers, there’s some important context to share.

My search was constrained by several factors:

  • I work in tech, and I’ve always worked in startups and SMBs, so with a few exceptions that looked interesting my search and applications were limited to this scope.
  • I work in information security, and in particular in information security leadership (“Information Security Manager”, “Director of Information Security”, that kind of thing), further limiting the scope of my search.
  • I was looking for opportunities that were either fully remote (with occasional travel) or in the Boston, Massachusetts area and accessible via public transit from Boston.

Given all these constraints it’s not entirely clear how applicable my experiences will be to other people. Having said that, when I spoke to my MassHire career counselor (a requirement for obtaining unemployment benefits) and told her I felt like my job search felt much tougher than it had felt in the past, she said she was hearing that from most of the people she was working with, so it definitely wasn’t just me.

OK, enough context, let’s do this.

I started my search the third week in January and stopped applying to positions May 14 when my I passed my background check at the U.S. Digital Service, since that’s when my job offer there turned from “tentative, pending background check” to “firm, you can count on this.” That means my search lasted for 17 weeks.

In that time:

  • I applied to 115 jobs
  • I had exploratory conversations with 5 companies which didn’t end up leading anywhere.
  • I was rejected by 52 jobs
  • I interviewed with eight different companies; of those, one offered me a job (which I took); I withdrew from one when it became clear to me that it wasn’t a good fit; and the other six rejected me (these are included in the rejected count above; the other 45 rejections came before an interview). All six of these rejections occurred after an extensive interview process involving at least three rounds.
  • Of the six jobs from which I was rejected after interviewing, I was truly excited about two of them, and I think I was a good fit and well-positioned for success at all but one. I guess that means I was extremely disappointed about two of the rejections, somewhat disappointed about three, and not disappointed at all about one.
  • I withdrew from consideration for 5 jobs, 1 of which was mentioned above, and the other four of which were companies that responded to my application after I had received and accepted an offer.
  • Doing some math, out of the 115 companies I applied to, 58 of them, or 50%, never responded to my application other than an automated acknowledgment. To be fair, I received such acknowledgments for nearly all applications, and many of them said explicitly that they would not contact me again unless they were interested in proceeding, but still, this isn’t a great number.

I’ve been working in tech for more than 30 years and I’ve never before had a job search where I was rejected this many times after multiple interviews. This felt both qualitatively and quantitatively different from in the past.

Non-numeric musings about my search

Digressing a bit from the overall “by the numbers” theme of this blog posting, I want to share some qualitative thoughts about my job search experience.

LinkedIn was my job-search HQ

As far as I can tell, just about every job opening in tech is being posted on LinkedIn nowadays, or at the very least such a large proportion of them are that you can just search there and find more than enough jobs to apply for. I can’t speak to the extent to which that’s true for non-tech jobs.

Nearly every weekday of the 17 weeks I was job-searching, I reviewed all of the jobs LinkedIn recommended for me as well as the result of several job searches (e.g., “information security”, “cyber security”). The browser plugin (Chrome / Firefox) I wrote to facilitate this reduced the time I spent reviewing job postings by more than 90%.

After my infosec-focused search I didn’t end up with an infosec job

As I hinted at above, I’ve accepted a position at the U.S. Digital Service. I’m looking forward with excitement to working on technology that impacts millions of people and makes things better for real people in concrete ways.

Having said that, I won’t necessarily be working directly on information security for all or even most of my time there. In fact, I won’t know exactly what I’ll be working on until I get assigned to a project, and there’s a good chance I’ll end up working on multiple projects with dramatically different responsibilities in each. The USDS tends to hire experts with broad experience and put them to work wherever they’re needed, a model which seems to have worked quite well for them.

You may be wondering how I ended up applying for and accepting a job at the USDS when I’ve been working full-time in infosec for the better part of a decade and was focusing on infosec roles throughout this job search.

Despite my daily job-searching on LinkedIn, I didn’t find out about USDS there. Instead I found out about it because Matt Bowen posted about it, Matt Hodges reposted Bowen’s posting, and I follow Matt Hodges. All this happened in the Fediverse (find me there), which is the only social media I use nowadays (I deleted Facebook years ago and deleted Twitter after Musk took over; you should too). Hodges works in civic tech and posts a lot about job postings in that field, and Bowen works at USDS. Amusingly, Bowen was also my first USDS interviewer after my screening call with their recruiter. I don’t know whether this was a coincidence or intentional because I mentioned I’d heard about USDS from him, but I suppose I’ll have the opportunity to ask him soon enough.

So, why did I apply at USDS when I was looking for infosec jobs? Because working in infosec was only one of my two priorities; the other was finding a job where I will be able to use my skills and experience to improve the world in real, concrete ways. Not to put too fine a point on it, but the world kind of sucks nowadays, and a lot of things are getting worse. There have always been lines I will not cross when looking for work, but this time around, I wanted to do better than just working to make some venture capitalists richer and making myself feel better about it by donating a big chunk of my salary to charity.

Don’t get me wrong, charitable giving is important, but it’s one step removed from doing good. USDS, on the other hand, is a place where I will be able to do good directly with my own two hands on a daily basis. That prospect was incredibly exciting and alluring to me, so I applied.

How working at USDS will impact my career trajectory

Before I accepted the job at USDS, I put quite a lot of thought into how working there would impact my career trajectory. It was not an obvious decision. I’ve done and enjoyed doing all sorts of things throughout my career, but I’ve really enjoyed returning to infosec full-time in recent years, and before applying to USDS I had assumed I would continue down that path.

Thanks to sage advice from my wife and from Tristan Marchette at Beacon Hill Staffing, whom by the way I strongly recommend, I came to the realization that not only do I not need to worry about how USDS will impact my career, in fact it’ll probably give me a solid career boost. Here’s why:

  • More than half of the people who leave USDS prior to the end of their four year tour of duty there go to work for other agencies whose projects they worked on for USDS. This is a feature at USDS, not a bug; one of the organization’s missions is to spread modern technical expertise into agencies throughout the government. So there’s a very good chance that, should I wish to remain in the employ of the federal government, working at USDS will be a launchpad for that.
  • I’ll probably have the opportunity to do at least some infosec work at USDS; my infosec dance card is not going to be empty for the next four years. Obviously security is an important part of the work that USDS does!
  • This is an incredible opportunity for me to refresh my hands-on technical knowledge, since I will almost certainly be called upon to do more extensive hands-on work than I have recent years. As much as I love infosec work, I also love hands-on software-engineering, operations, and data science work, so I’m going to enjoy this aspect of the job, and it will make me more employable when I leave, not yes.
  • If I decide to leave government service after USDS, having worked on projects of the scope and scale that USDS tackles will be a big asset for my résumé. If I want to go back to infosec, then it my USDS work will prove that I can tackle infosec at scale, not just for small startups.

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