Every week, CTO Academy hosts live sessions and debates with seasoned technology leaders and career coaches. Members can ask questions and get immediate answers from experts. Last month, one of our sessions looked at the major shift in tech job market trends. Our guests, CTO Sean Handley, founder of London CTOs Barry Cranford, and career coach Adam Horner, explained what has changed and how to adapt to the new reality.
Here’s the bitter reality in a nutshell: the job market for technology leadership roles has tilted significantly in the last 18 months. By some accounts, it has been the worst job market in the last three decades. However, on closer look, the situation is not nearly as bad as it appears at first. You’ll understand why shortly.
First things first:
Long story short, major layoffs in tech companies, triggered by the increased cost of money, consequently led to (seemingly) decreased demand for leadership roles.
For years, new tech companies were popping out all over the place. However, rising costs, reduced profits, and the cost of debt ultimately forced these companies to downsize and consequently flood the job market with tech professionals.
Even tech startups, once the sponges of massive employment of software engineers and technology leaders, are now bootstrapping or hovering in the stealth mode for a lot longer than they used to. Many have run out of money and shut down their operations because VCs are becoming more cautious.
Historically, the Tao of tech startups was to hire en masse and figure out the monetization later. What made that possible was the more than generous funding. However, with VCs pulling the brakes on their once wild chase for the next tech unicorn, fewer of these startups can survive.
According to some, all of this has caused less demand for senior technology leadership roles. Teams are getting leaner, including SLTs, even though the complexity in most companies remains relatively unchanged.
However, the reality is different.
We did a fresh job market research and ran a historical analysis to see if anything changed in the last 12 months. The data indicates divergent trends between the US and UK CTO job markets over the past 6-12 months. The UK shows a clear decrease in the absolute number of available CTO positions but with significantly increased compensation, suggesting companies may be consolidating these roles while placing higher value on them. The US market, on the other hand, maintains a high volume of positions across platforms.
So the demand is still here, at least in the US. Which means that the problem lies elsewhere.
But before we unveil the real issue, we cannot bypass the elephant in the room, Gen AI.
No matter how hard the tech community is pressing against the ability of AI to produce working code, nobody can dispute the fact that AI-assisted programming has enabled companies to drastically downsize their teams. Most notable examples include Spotify, Klarna, and Amazon, especially for code migrations.
Sean Handley, who wrote a blog about his experience with job hunting after being laid off in December 2024, said this on the subject: “There is something I didn’t put in the article, which I was kind of loath to put. In pretty much every process where I spoke to a human, they wanted to talk about Gen AI stuff. There were always questions about how do I use Gen AI, what its value is, what the pros and cons are, and what the risks are. Then, it would get more personal, like how am I using it personally, or how are my teams using it? That’s definitely been the thing that’s sort of been seismically changing what it means to work in tech. And to be honest, that’s been one of the most frightening things. I mean, it’s like I’ve spent almost 20 years getting myself to a point where I feel like I’m good at something, and suddenly all the rules have changed.”
The bottom line is simple: fewer people means reduced necessity for leadership, which translates to fewer universal CTO roles.
Which brings us to the new reality of a CTO role and the real reason why some former technology leaders are now on the job market.
Let’s not forget that the CTO position is relatively new. It’s been around since the late 80s, and, in the past, experience in technology and Ivy League education were the two major qualifications to get a job.
Lately, however, executive teams are looking to hire the right kind of CTO instead of a general expert. That is, they are looking for specific subject matter expertise. And this shift occurred only recently, some 12 to 18 months ago. For example, you will now often see that a company is looking for a Field CTO rather than a general Chief Technology Officer because the role demands active client engagement, which was unheard of in the past. Historically, CTOs were invisible to the customer’s eye. Today, however, they are often at the forefront of the sales strategy as the product’s evangelists, especially in B2B sales.
According to Adam Horner, and as it’s been implied throughout Sean’s blog post, the difference between success and failure in job applications is now in optimal and clear positioning.
What is optimal and clear positioning?
Ask yourself this:
This is the value you are bringing to the company that makes it unique and specific. It can be industry expertise, sector expertise, or solving ad hoc problems the company is currently facing (e.g., migrating a monolith). Whatever it is, those specific skills, backgrounds, and experiences set the foundation for positioning.
With well-defined strengths in your pocket, you start picking your roles by focusing on those that best fit your core competencies and expertise. As we established in one of our recent articles that looked at common errors in CTO resumes, if you do not have a relevant portfolio sample, you are not 100% qualified for the job, regardless of your years of experience and education.
So the question now is:
In other words, should you ditch the broad networking/broadcasting strategy and attempt to build a niche-level authority position?
The short answer is yes because, in the past, you could simply just be a CTO; however, that doesn’t cut it anymore. Today, you must be area-specific (i.e., cloud integration is my area of expertise, and I reign supreme in it).
There are more CTO roles now than it was before. These roles are distinct and verticalized because technology has become a basic requisite for ANY company or organization. You just need to define where exactly you fit in, in what we can now call the spectrum of a CTO role.
But what if you are a generalist?
You’ve kind of done a little bit of everything. You’ve been in tech for two decades, coming in through program management and not necessarily as a developer. Nonetheless, you managed to work your way up to a CIO role where you were responsible for cloud infrastructure, engineering, and cybersecurity. You also worked in product development and customer success. Basically, you are not exactly a hands-on engineer. So, how do you differentiate yourself?
The general advice from Adam Horner is this: pick something. In other words, pick your favorite thing that can make the biggest difference out there. Focus everything around that one thing with a recent track record and sell yourself based on that.
Once you get to the point of the interview where you can say, “I can solve this problem. I’m good at this problem. I’ve faced it before and I can solve it this way,” the follow-up questions will start coming, “Oh, can you also solve this? Can you solve that?”. That’s when your generalism comes to the fore.
Therefore, lead with your specialization, but always remember that your generalism is an added value because you know how elements fit together: from product development via data analytics and finances to customer success. And that’s the bit that’s likely to put you in front of the competition.
In the not-so-distant past, technical expertise was enough to get you a senior tech leadership role. Today, on the other hand, you must possess a clear understanding of where and how exactly the technology adds business value as well. Which means that, besides practical coding, technology management, and team leading experience, you need to have strong business acumen. Without it, it is going to be close to impossible to design and align technology strategy with the company’s business goals and know when to pivot. To put it bluntly, the days of CTOs hovering above their engineering teams and being clueless about what’s going on outside their bubble are long gone.
This is the reason why modern technology leadership programs place much focus on business-related modules instead of just teaching team leadership and technology management. Because, in the end, it’s rarely about the tech. It’s more about running a successful business, and that implies nuanced knowledge of how businesses operate in different market conditions.
To give you an example of such a curriculum, we’ll take a brief look at the lectures in the Digital MBA for Technology Leaders that are relevant to our topic.
Out of nine modules, three are focused solely on business fundamentals, finances, funding, and aligning technology strategy with business goals. We are talking about 75 dedicated lectures that cover every single aspect of business operations from a non-technical perspective.
These lectures build the critical knowledge required to execute your responsibilities as a modern-day (even area-specific) Chief Technology Officer. Without it, even if you are in a tech leadership role at the moment, you might soon find yourself stepping back to hands-on engineering rather than leading teams because you are missing a fundamental understanding of the convergence of technology and business.
As a rule of thumb, these programs include memberships and alumni access that is arguably the single most important asset in your arsenal when seeking a better or new job.
Barry Cranford, the founder of London CTOs, told an interesting story. Earlier that day, when we were hosting this particular live session, Barry had lunch with a fellow CTO who recently started a Fractional CTO role after spending four months hunting for jobs. At one point, he almost gave up because he felt like he was trying too hard. He was pushing himself on LinkedIn and applying for too many jobs, but not getting anywhere. Until the guy he got drunk together at the conference in Barcelona seven years ago, noticed one of his LinkedIn posts and sent him a message that led to his current job.
This is the story that repeats itself over and over again: a network eventually comes through.
How to find and navigate the ideal community of technology leaders?
We hear it from our members all the time. They get hired thanks to the push from the people they worked for or communicated with. And more often than not, it has nothing to do with the actual job application, but with peer-to-peer networking.
So instead of relying on your LinkedIn CV as the first impression, get into the community and connect with people.
When you first meet someone, don’t immediately tell them that you’re looking for work. — Barry Cranford, London CTOs
As Sean himself admitted, “At first, it was emotionally difficult. Rejections and ghosting get to you. But after reaching out to other people whom I knew were job seeking and just checking in with each other, you start to feel a certain ease because you are not alone. There is a bit of camaraderie there that is genuinely super helpful, which makes other conversations easier because you are not approaching it from a negative standpoint anymore.”
Be very mindful about your social posts. As the final stage of the hiring process, the recruiter is more focused on the negative stuff; for example, a post in which you vividly describe your discontent with the job market and recruiters. Even if the interview has gone well, this textual relief valve you used to make yourself feel better will most likely result in ghosting.
Another interesting angle to the whole networking strategy is attending non-technological events or events in different industries.
People talk about their problems; it’s inevitable in these types of gatherings. Often, they don’t realize that someone with a background in technology can solve some of those problems. So, from just another attendee, you turn into an asset or a magic bullet, if you will.
As one of our members said, “Tech events are saturated with all the same people that are competing for the same thing within the realm of the same mental space.” In non-tech events, on the other hand, you might be the only “IT guy,” remember that.
Combine it with the strong global community of technology leaders, and job seeking will become significantly easier.
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