A Job Search During Mass Layoffs: My Experiences and Thoughts

As I've alluded to in past posts, I'm currently in the process of winding down my one-person, bootstrapped cybersecurity startup since it has not been the financial success that I had hoped. That means that for the first time since undergrad (i.e. 15 years ago!), I'm actively seeking a job.

Suffice it to say that today's job market is "not one of the best" for tech workers. With several hundreds of thousands of employees laid off across the last few years in just this sector of the economy alone, there are a lot of displaced employees fighting for open jobs in the companies that are hiring.

I've been a professional in cybersecurity for 11 years and in the tech sector for 9 years, and I'd very much agree with the frustrations that others are having while searching for a job right now. And since I'm still on the market as I write this, everything could go sideways, but it does look like I'll have a couple of very strong offers coming in the next couple of weeks after 4 solid weeks of searching.

Given my experiences (and as someone who has hired and built a full team in the past), I wanted to share my thoughts and suggestions if you find yourself in the market for a job (either by choice or not!).

Leverage your network as much as possible

Over the course of my education and career, I've had the great fortune of working with many incredibly talented classmates and colleagues in cybersecurity. I've also been lucky enough to interface quite a bit with customers, sales, marketing, engineers, founders, and venture capital leaders in my roles.

Before COVID (and somewhat in the last year or two), any time I would travel to industry conferences or workshops, I'd make it a point to reconnect with as many people as possible. This was predominantly because I enjoy learning about how everyone's careers and lives are going, but it also serves the purpose of keeping these people "on my side."

Inevitably, some of my colleagues and former coworkers have lost their jobs in the last few years. Whenever that happened, I would always share their information with my network and–when appropriate–add more color about the character and quality of the person who was now thrust onto the job market.

While I've not publicly announced that I'm closing down my current company for a couple of reasons (which means I can't directly take advantage of the broad reach of a platform like LinkedIn), I have reached out directly to about a dozen former colleagues to get their feedback and help with finding the right next position for me. It has been an incredible help!

Through a few of these connections, I've been introduced to founders and C-suite leaders of companies across the industry. These introductions have led to personal discussions (with executives who are already oversubscribed with TODOs!) where we mutually explore exactly where I might fit in their organization. The outcome of this has frequently been my learning about a job that was proposed but isn't yet publicly posted, being fast-tracked to the top of the list, and getting the opportunity to really see the values of an organization modeled first-hand. Hands-down, this beats the standard path of:

• trying to decipher the actual role behind the job description
• missing job opportunities due to the roles being named/positioned differently than expected
• being passed over by a recruiter due to discrepancies between keywords in your resume vs. the job posting

Don't apply to jobs you won't enjoy (unless you're broke)

Being unceremoniously pushed out of a company due to mass layoffs is something that I imagine would be a terrible, helpless feeling. Fortunately (at least so far), most of those layoffs have come with a pretty cozy severance package, which I'm sure takes a fair bit of the sting out of it. However, not everyone is so lucky. That brings me to my next suggestion.

I view the opportunity to search for a new job as an infrequent chance to reflect on my career and think about what actually suits me going forward. Most people in their day-to-day roles don't lift their heads up to look around and constructively think "is this what I really want to be doing?" Life gets in the way like that.

I've used the last 4 weeks as a time to deeply think about:

• what day-to-day activities give me energy vs. drain my energy?
• what part of the industry (for cybersecurity, that might include thinking about offensive/defensive/intel/research, vendor/services/internal, private/public) do I want to be in?
• how important are different aspects of a role (% of travel, meetings, coding, leading, ideating, creating, etc...)?
• how important is compensation, title, and impact?

For example, I've learned that I care deeply about the mission from the vendor side of security, I need a high-impact, high-visibility role, and ideally the role would be a technical leadership role that works cross-functionally with other teams to drive the creation of cutting-edge technology. I also know that while I'll travel part-time for the right role, I am—having been remote since 2017—through and through a remote worker.

Even though there are a lot of unfilled security jobs open right now (as there is a shortage of high-skilled workers in this space), there are quite a lot of jobs that don't align with what matters to me. This saves me a lot of time and effort when applying to roles, as I won't apply unless I actually believe that I would enjoy doing the work described for at least 2 years.

Don't be afraid of job descriptions

Probably one of the most frustrating things I've encountered while searching for my next position is ridiculous job descriptions. While there are a few out there who very clearly state what is actually required vs. preferred, many of the JDs I've seen are unreasonable.

The approach I've taken to these JDs is to look at what the actual roles and responsibilities are, identify if I can excel there (or quickly learn what I need to round out my gaps), and apply accordingly. I'll usually address any perceived gaps—and how I plan to overcome them—in my cover letter.

Know your floor compensation

Even though I see an overwhelming number of jobs posted online, many of them are easy to filter out by their compensation numbers. Knowing rough compensation in many tech jobs (and certainly the ones I'm interested in) is possible thanks to the rise of remote work coupled with a law passed by California in late 2022:

Now that employers are required to post the pay scale of jobs that might hire a worker living in California, it's relatively easy to understand whether or not the company is competitive for your skills in whatever market you live in.

That said, I've noticed a couple of things employers still do to make it confusing. First, for some positions I see gigantic compensation ranges. This is better than nothing (since you know the floor and the anticipated limit), but it provides little information about whether you're accepting a fair offer if presented one.

The second thing I've noticed is that no companies provide details about the size of bonuses or how much equity the position may offer. This is quite frustrating, since as a person moves farther into their career, bonus and (more important) equity compensation makes up a significant portion of their earnings (and, when leveraged correctly, their net worth).

In order to combat this, I've used my compensation numbers from my last employer, compensation details from conversations with friends, and a review of what we actually need for our desired lifestyle to determine whether or not a position fits within my expected compensation range. Doing this has helped me significantly filter down the job postings I'll consider, and it has helped me to avoid a lowball offer a major public company gave me before I officially began my job search.

Compensation is more than just numbers

While you're searching for your next position, it's important to remember that compensation is much more than just the numbers (base salary, bonus, equity) you agree on. Base salary is probably something you can rely on for your day-to-day expenses (beyond getting laid off or having a company- or group-wide pay cut), but the remainder is highly variable in its actual value.

Starting with bonuses, be aware that they are often tied to company- or group-wide performance rather than your individual performance. That means that even though you might be knocking it out of the park in your role, your compensation might be reduced due to the company's overall performance. This is even more true if you're a public company, since stock prices may be affected more by the overall stock market rather than how your company performs. I always consider this kind of compensation as unreliable and would never count on it for my day-to-day lifestyle.

Equity compensation is a whole 'nother beast. First, public companies' stock prices are subject to the whims I described above. In addition, comparing offers from two different public companies is not as straightforward as it sounds. For example, looking at the five-year performance two public companies in the tech (and cybersecurity) sector, it's clear to see that a $100,000/year RSU package at both is not equal.

If you instead decide to consider a venture-backed startup, the comparisons get far murkier. First, the likelihood of the company succeeding vs. failing is significantly different in every round of fundraising. To compensate for that, earlier-stage startups often offer much higher equity packages to their early employees (side note: treat that equity package as a lottery ticket that you should never count on for day-to-day income).

Additionally, be aware that often startups will succeed through a merger or acquisition. With rare exceptions, the actual value of your equity package will be far less than what you (and the person who hired you) had anticipated. In fact, in some cases, those exits (as they're called) actually lead to no equity compensation being passed along to rank-and-file employees. I went through the former, and I know people who have gone through the latter.

In my search, I'm actually working through this challenge myself. One position I'm interviewing for is with a public company with a stellar track record that provides roughly $100,000/year in RSU compensation. The other front-runner is a Series C startup with excellent recurring revenue, a high valuation, and a strong bias towards IPO in the next few years. Their equity package is closer to $50,000/year, but it could become much more valuable in a short period of time if they continue executing as they have. Because I don't need to count on those earnings for my day-to-day and I have a bias towards earlier-stage opportunities, I'll—if I were given both opportunities—likely take the latter.

Know how to learn

When I encounter people in tech who are stuck focused on one particular methodology, one programming language, or one general tech stack, I avoid them at all costs. In my (not too controversial) opinion, the time is long gone where someone could get a degree, focus on a few technologies, and spend 30 years cranking away. The changing pace of technology is far too great, and AI just lit that pace on fire across the last couple of years.

Knowing how to learn is far more important than any one technology or stack. Being able to pick up something brand new, deep-dive on it, and become proficient or expert in a short period of time is the key to your upward trajectory. And with LLM-powered chat bots like ChatGPT, it's easier than ever to leverage the world's knowledge to become highly skilled in very little time. In fact, it's how I went from not coding for 5+ years and having no cloud knowledge in 2022 to designing, architecting, and building a complete SaaS cybersecurity product in just a few months. And while the startup itself isn't financially viable to continue long-term, the skills I learned building it are exceptionally valuable!

Wrapping it Up

If you're on the job market like me right now, you know how frustrating and anxiety-inducing it is. If I had to wrap up the above into some key takeaways, they'd be:

• take some time soul-searching about what, where, and how you actually want to do work going forward
• ignore everything that's not compatible with the above (unless you need any job right now)
• use your network to get VIP-level access to opportunities and companies that are highly-compatible with your goals
• leverage AI to supercharge your ability to learn and be flexible on the job

And no matter what, keep your head up and keep searching!