In one of our most recent online sessions, we discussed the troubling trends in the tech job market, especially in the technology leadership category (e.g., CTO, fCTO, Head of IT, etc.). In some instances, it can take up to 18 months to land the executive role. While the shifts in the market are partially responsible, your CTO resume might also be the cause for such a dramatic lag or inability to even land an interview. Paradoxically, it is that same resume that unlocks the door and lets you in.
Therefore, in this guide, we walk through the essential elements of every CV and explain the capital rule of job applications, regardless of the role’s seniority or even the type of job, industry, niche, or organization. We also use the most recent CTO job ad from Glassdoor to better explain the optimal resume strategy. So, to avoid the frustrations caused by repeated rejections or ghosting and a lengthy application process like Sean Handley experienced, this is the one CV guide you should carefully review.
The two parts of the CV, the cover letter and resume, aren’t about you; they are about the organization and the role you are applying for.
This may sound a bit contradictory because we all like to think that the purpose of a good resume is to reflect all our amazing skills and accomplishments.
Well, that’s only partially true, as certain specific experiences may be irrelevant—or even detrimental. That is, listing them takes attention away from what a potential employer is mostly interested in.
Now, let’s explain what this means in practice. We’ll start with the basics: the key elements of every resume.
There are six key elements you must include in a CV. In their correct order, they are:
Work experience is merely listing all the roles and the companies you worked for. Portfolio, on the other hand, is that one true asset that ticks just the right boxes. Sure, you can use them interchangeably, but…
Ask yourself an inevitable question: What separates you from 50 to 60 other candidates applying for that same job?
Think about it. You all have a university education, 10+ years of work experience in the private and public sectors, and experience in leading cross-functional teams and building solutions. So why would they hire you instead of any of them?
It comes down to two things: a cover letter and a portfolio.
These two are used complementarily to a) address the problem that made the employer search for the new employee in the first place, and b) prove the undeniable expertise in the matter.
Many falsely believe that a portfolio is only used by those building products and services. For all intents and purposes, an example of successful completion of the digital transformation process in Company A and the successful migration of the on-prem, monolithic system to the cloud infrastructure in Company B are, in fact, portfolio samples that can land a job in Company C. You only need to emphasize them in your cover letter.
Which leads us to the most common mistakes people make when applying for jobs.
There are two capital mistakes you want to avoid at all costs, especially if you are a serial applicant (i.e., using templates to apply to as many jobs as possible in the shortest time due to growing frustration):
#1 causes #2 leading to a junk CV and continuous frustration. Remember that.
Before applying for a job, you must determine why that organization is even looking for a candidate for that particular role. In other words, you must do your due diligence and research the organization from every possible angle. Without this investigation, you can’t prioritize skills and portfolio samples that will enable you to stand out from the crowd.
(We call it samples because they are fragments of the overall role you played in an organization, the scope of which most likely far exceeded just that specific part.)
(Especially if the company outsourced the hiring task and you don’t know the company’s name.)
Let’s take a look at one of such recently posted CTO jobs on Glassdoor.
According to the outsourcing company, the employer is a “technology-driven organisation that utilises advanced data processing and modelling techniques to develop industry-leading solutions. Operating in a competitive sector, they focus on creating innovative and scalable systems that drive impactful decision-making.” In other words, they are building analytical and monitoring tools with different tiers to expand the market reach.
The list of responsibilities is generic; something you commonly see in these types of job ads. But when you scroll down, you find the real juice: Essential & Desirable Skills and Experience, where a few requirements simply stick out:
It’s here where you can see their problem and the driving factor behind the decision to hire a (new) CTO. And in this particular case, it is these four requirements that you must address in your cover letter and then back them up with portfolio samples.
For example, experience with Python indicates that they are looking for someone with a strong technical background. Algorithmic modelling and complex data environments most likely mean that the ideal candidate possesses hands-on experience with AI-powered analytical and decision-making enterprise-level solutions. That’s why they are looking for someone who already knows how to leverage complex data.
Therefore, you need to prepare three distinct portfolio samples that, ideally, complement each other: programming, modelling, and data management.
One remark here, though: if it’s not Python, then make sure the algorithmic modelling is closely related to the type of solution they are looking for, because they have clearly emphasized that specific programming language, which means that their teams are using it. In other words, if you lack one, compensate with the other.
Think of those portfolio samples contextually in your cover letter and blend them in to strengthen every statement. That is, answer each of these “questions” with the actual successful examples of your past work, relevant to the exact requirement. Do it right, and nobody will even read the next page of your CV, but simply schedule an interview.
In case you do not have a relevant portfolio sample, you are not 100% qualified for the job, regardless of your years of experience and education.
As you can see, running specific job requirements against your portfolio gives you an immediate clue about your eligibility. It saves time and nerves if you are applying for multiple jobs. Use your portfolio to filter out or, at the very least, prioritize applications.
If the company is looking for a CTO with experience in building an X type of solution, find a similar product you worked on in your past and wave it in front of their eyes. Make it the center of your cover letter.
Finally, when listing your skills, follow the exact order the employer used in the job ad. In other words, simply reiterate with a bit of different wording.
Now, you might be wondering about this specific format of a resume with the focus on the cover letter and portfolio, but when you are competing for a job in a fearsome competition, you want to attack with the tip of your spear and not the edge of your shield.
So…
The order of CV elements in traditional templates starts with a photo, basic personal data, education, skills, and work experience. By default, they all include a cover letter, which most disregard, ignore, or fail to write optimally.
This might sound controversial, but such an order is not aligned with the employer’s interests. They (employers) primarily want to know two things:
Only if these two answers satisfy them, they’ll move to your name and that lovely filtered photo of you in the suite.
I’m convinced that a huge amount of candidates are rejected simply because the hiring team didn’t have a strong enough signal from the hiring process. — Sean Handley, CTO
So, if you imagine a pile of 60+ resumes on someone’s desk, which one would you say will attract immediate attention:
The one that opens with the solution to their problems or the one with the photo, name, and address?
In case you don’t have a referral with the power to put your CV directly into the hands of the decision maker, your cover letter is the only thing that can potentially put you at the top of that pile.
As Adam Horner, Berry Cranford, and Sean Handley repeatedly stated during the session, your best chance of landing a job quickly and with minimum effort is through a referral. And that’s where a global community of technology leaders supporting each other and frequently posting jobs in dedicated channels comes extremely handy.
Therefore, if you don’t have a network, your only asset is a fine-tuned resume.
90 Things You Need To Know To Become an Effective CTO
