Adversary Intelligence: Job-seeking advice from a “Corpo / Hiring Manager” Perspective – Resume crafting

April 3, 2024

Introduction / Background

This post was born from a series of thoughts, principles, and frameworks I’ve used while coaching job-seeking professionals in the security and tech fields over the last year, which I’ve greatly enjoyed.

Many of those individuals struggled with presenting themselves in a way that both catches attention through their success yet is authentic and accurate, and I found myself recounting a lot of the same advice over and over again… which led me to put the below to pen in hopes of helping a broader audience than those I can fit into my volunteer hours each week.

Why listen to me? I’ve worked in financial tech (“Fintech”) 18 years, with well over a decade of that building and managing teams. With over a decade in the hiring game, I’ve seen enough resumes to fill a server room – twice.

I’ve been the dread “hiring manager” that job boards warn you about.

Let me use those experiences to help you raise the chance of your resume being in the <5% that don’t STAY forgotten in that server room.

From here, I’ll:

Give advice on your goals for your resume as a candidate
Provide perspective on the “other side” – hiring managers, talent agencies etc. – “know The enemy” – and by the way, lesson 1 – we are not the enemy.
Provide practical tips on all of the above

If that sounds interesting or useful, read on.

Your goal as a candidate

As someone looking for a new role, your job is to show what you bring to the table, and specifically, why you are a better bet than a hundred (or more) other options that might be on the table. Every company and hiring manager is playing a probability game – there are no guarantees in hiring.

Figure out your brand – what makes you unique. Are you the rare techie who “Speaks business”? Do you thrive in bringing order to unruly / chaotic environments? What’s your niche? When I see someone who is a “technical leader passionate about vulnerability assessment” and has skills / accomplishments to back it up, I’m much more likely to reach back out than I am for someone who is a just a “developer seeking a position to use my skills to greatest effect.”

But, don’t get too unique. I’ll cover this more below, but while your hobbies and nonprofessional endeavors can help you, overemphasis or undirected information here can also hurt you – balance and reasoned disclosure is key.

A good example – I once coached a person who featured their position in the LGBTQIA+ professional group at their previous employer on their profile – this was not directly work related, so not directly telling me “you can do the job”. Had it just been that, I’d have said “leave it off, not directly helping your case.” BUT they were in a leadership position in the group, managed finances, planned events, dealt with PR… etc. These are all transferrable soft skills. That? Resume gold.

Contrast that with another candidate who prominently displayed their membership in a local anime group / community, and a few Japanese-language and culture centric groups. That’s nice, and who doesn’t love consuming some Satoshi Kon or Hideaki Ano here and there… but it doesn’t tell me anything useful about your abilities to do any job (unless you’re applying for an in-industry job, which this person was not).

Know the enemy…which is me…

From the job-seeker’s perspective, the hiring manager and the recruiter can feel like “The enemy”. They have the power, holding the jobs and the money, the decision rights. Seemingly capriciously, they filter people in or out of opportunities, they are why you don’t have your dream job.

But, to use a phrase from Jason Blanchard – “jobs don’t hire people, people hire people” (check out his job hunting videos on Youtube if you haven’t yet – they are great).

Those hiring managers are people too, and have their own concerns. As someone who’s been on both sides of this divide, with a lot of that as one of “those bastards” doing the hiring, here are some common thoughts going through the heads of people on that side…

I’ve got a capacity or capability gap I need to fill, either because someone left, or because my team is taking on some new responsibility – I need to fill it ASAP with a good person, so we don’t get overwhelmed.
I want to bring in someone who will be hold down the fort now, but also be an awesome long-term addition to the team. I want to be picky and find someone who can kick butt on day 1, day 100, and day 1000. I’ve literally passed candidates because they admitted, when I asked about their lack of either learning or advancement, that they were happy just doing the same thing over and over.

Now, not everyone needs to become a people manager, but you should always be hungry to learn and develop – and your resume should show that in your chosen space.
My time is limited – my team has existing problems, and I have other stakeholders breathing down my neck… I can’t spend much time on any one candidate given I need to assess many.
My people are an investment – I’m going to sink lots of time (mine and others) and money into onboarding whoever I hire and helping them develop. I’ll look at you and try to figure out how fast I’ll recoup that investment.

What does that all mean practically for you?

Hiring managers are not out to “get you” – they’re looking to solve tough problems they DO know with something they DON’T know (you).
Hiring managers have limited time – You want to make sure you do everything you can to show value and not be a drag.

When I was hiring into my teams in my last big corporate gig, I was also preparing content for the CTO, meeting with senior business leaders and developing long term strategy and plans – it was a lot! With all that, I managed to carve out 1/3 of my time for hiring, and could have easily used more time, but couldn’t. So I needed to make the most of it.

If you make things easier for “me”, by being clear and concise in your communications, making your impact obvious etc… I’m more likely to give you a second glance.
Hiring managers want problem solvers – related to the above – anything you do to show initiative, capacity, etc. will serve you well. Do you have experience AND traits like drive, initiative, or creativity? If so, you’re more likely the person I’ll hire.
Hiring managers have to worry about downside risk – bad hiring decisions can have big downsides for their teams, themselves and their own bosses, and the company at large (depending on the nature of the issue). So, they’re incentivized to have very high bars for bringing people in, which can come off as “picky” or “choosy”. So for you – little things matter.

As an anecdote on the human side of things – I was once late for an interview, due to family situations (we had recently welcomed a new child into our midst, with all the related complications), and the candidate, though seeming offput by body language, diplomatically asked if everything was OK on my end, “was there a team problem I needed to deal with”, and should we reschedule. I gave a brief explanation and apology, and we went from there. They were understanding, engaging, and moved from “looks offput” to “in the game”… The fact that person both gave me human grace, yet still asked an insightful question about my org, stuck with me. Here was a person I could imagine being part of my team, and we went forward from there.

You have personal challenges, so do the faceless “hiring manager” and “Recruiter” – meet in the middle. Don’t be a doormat, still ask good questions, but – be a human.

OK then, so what do I do practically?

Getting in the door – your resume / CV

Your resume is the first “filter” that can make or break your ability to land a role you want. Talent agents, recruiters, hiring managers, and others use it to get a quick view of whether it’s worth an hour to talk to you further. As one of many options on the table, you’ll need to stand out and make “picking you” be easy for your reviewers.

How? Read on…

Goals

You have a few goals with your resume or CV…

Get past machine-based scans and filters
Provide a view that showcases your skills, experience, and abilities that align with a particular role / industry
Highlight the impact you’ve had, not just what you’ve done
Make any other positive “x-factors” clear for a hiring manager

Your goals ARE NOT

To provide an exhaustive view of everything you’ve ever done & how you did it.
Sell yourself above and beyond the confines of reality.
To provide a window into your “Extracurricular” activities, hobbies, and social or political views**
Opine on anything else in the world writ large.

** Handled well, which is rare, some of these can be an asset

Researching the company can be a useful step, but I would hesitate to put too much effort into making your resume company specific – rather than tying things to specific company problems or goals you’ve discovered from a news search, instead focus on underlying themes or types of problems, which will parlay well at the company in question as well as others.

You want to be as impactful, interesting, and professional as you can, “on paper”, in the shortest space possible, so that you can secure the next step – an initial interview / phone screen.

Resume Structure and Content

Going back to “Hiring Managers have limited time” and “hiring managers are looking for problem solvers” – you want to present yourself as efficiently as possible, and put key information highlighting your impact, ability to handle tricky problems, and leadership, front and center.

This results in a few practical tips:

Keep it short and simple.
- Start with a single page, and simple formatting
Lead with what is most important to landing the role
- Tailor your resume to each application, or at least a given sector
Showcase your accomplishments, impact, and leadership
- What do people remember you for in your last roles?
Filter out content that is not helpful
- As in #1, tight messaging is key.

1. Keep it short and simple.

Base resume length is a page, with simple formatting.

You can add one more for 5 – 10 years RELEVANT professional experience. Mine is 2 pages. I’ll likely never go to 3.
Relevant is also key here. If you’re looking for a role materially different from your past experience, don’t spend time / space “selling” that previous experience – though you may want to highlight a few transferrable soft skills
Be succinct! Lead with action verbs, and simple, one-line statements covering impact or skills.
- DON’T: “Developed and executed an enterprise-wide audit program covering hundreds of security controls, establishing a maturity baseline for external inquiries, the results of which drove strategic roadmap changes in key areas such as access management and vulnerability management.”
- DO: “Established an audit program spanning 100’s of controls based on NIST, ISO 27001, & CIS standards. “

Keep your formatting simple. Most companies feed resumes into an Applicant Tracking System (ATS), which acts as a combination of candidate database, interview feedback compiler, and more. They parse your text resume and try to put it into a structured format for searchability.

Avoid tables, fancy indents, inline columns or images, etc. – ATS can’t parse them.
Do Use simple whitespace, tabs, bullets, and clear section headers
Left justify as much as possible after your initial contact info and objective.
- Recruiters and HM’s tend to read “F-style” across the top, then down the left side to scan for relevant roles / experiences, then right for details when they see something interesting. Structure your content accordingly.

I break with Jason B, whom I linked to above, on this, he advises to be a completionist and not sweat the length because most resumes are read electronically these days, which is less cumbersome.

I take a different stance (from my own experience) – If the hiring manager doesn’t have time to read 8 printed pages, they don’t have time to read 8 electronic pages.

You should make the most of the space, keep it slim and focused.

2. Lead with what is most important to landing the role

Many people think of a resume as a static artifact, yet the best resumes adapt to the hiring circumstance and role on the table.

You should have a “master” resume copy, with all your experience laid out succinctly and with impact, but, when you apply, you should make a role or sector specific copy that re-orders things, omits things, or highlights things in such a way as to paint your qualifications for a specific role or space.

Example: I have a master resume, as well as a version focused on my security and risk experience, and another focused on my operational experience. I use whichever aligns with a given role. For a truly nuanced role, I might refine a role-specific version.

Put whatever makes you most qualified for this role up front. If that means your work experience, lead with that after your summary, as is the conventional wisdom. If that means your certifications, or formal education, etc., put that up front instead.
If you’re changing career tracks and don’t have practical experience in your new field, you might want to lead with education, projects, and other experiences first. You can include a “professional experience” section towards the end of your profile- a filtered view of other experience focusing on soft skills that are transferrable to your new role, not an exhaustive list of everything you’ve done.

3. Showcase your accomplishments, impact, and leadership – use the STARS method.

Many resume services (myself too!) will tell you to use the STARS method – you can read an in-depth discussion here – https://topresume.com/career-advice/how-to-use-the-star-method-in-your-resume – but I’ll summarize the most important points here.

Basically, it’s about showing HOW you solved a PROBLEM and what your direct IMPACT was.

This demonstrates your unique value-add by highlighting your lasting contributions and practiced skills. Concretely:

Tell me your impact. Did you create additional profit? Reduce a cost or risk of doing business? Force a clear decision or discussion where there was none before? Build or document a process? Tell me what you did that someone else in the same role didn’t do or wouldn’t have done.
Tell me the scope of what you did. Overseeing a vulnerability management program on 3 Windows servers & 4 desktops is one thing, but doing the same over an enterprise with 1000’s of endpoints, multiple OSes, and custom software per-host, is something very different. Yet, both are “running / overseeing vuln management”. Which did you do?
Tell me how you did it. This is your chance to practically showcase those skills. Don’t just tell me that you reduced the daily operational burden – Tell me how you “Reduced operational workload by ~40% by automating common maintenance tasks using a combination of Python and bash scripting“. You just showed me impact AND practical skill.
Show me where you displayed leadership. That doesn’t just mean managing people, but did you take the initiative somewhere? Propose a change and then push to get it prioritized or accomplished? Lead a project across disciplines and teams?
Avoid “Responsible for..” – or at least summarize. The weakest bullets in an experience section say things like “Responsible for [X]” or “Did Y”. While those inform that you have experience in X or Y, just about any candidate from a similar work background will also have that experience – you’ll be much more attractive if you can tell me your contributions.
Concrete example combing all of the above:
- BAD: “Responsible for the user-facing customer service desk.”
- OK: “Responsible for the user-facing customer service desk, wrote runbooks to improve service desk quality of service”
- BEST: Led user-facing customer service team to increase satisfaction survey results from 75% to 97% by implementing common runbooks to improve consistency of service.

4. Filter out content that is not helpful (and tailor your resume to content for a specific role)

This one is tricky for many people, especially experienced professionals with a wealth of job history or those changing job tracks / careers.

Going back to the idea of “lead with what is most important” – you also do not want to spend time / space on things that are not directly helpful.

This can take a variety of forms, but the most common practical applications are:

If you have work experience not directly related to the role you’re looking for, either don’t mention it, summarize it, or put it later in your resume.
For those experiences you retain, filter the accomplishments down to applicable soft skills.
Details on experiences 10+ years ago are less important / relevant. It’s not “recency bias”, it’s pragmatism on the part of hiring mangers. Sure, you did helpdesk when you were a teenager, but is that really practically applicable to the role you’re applying to now, as a 30-year old mid-senior developer? Either omit such roles, or summarize in an “Additional experience” section as “role, organization, years”.
I (as a hiring manager) don’t care about your hobbies or views. Some people may advise folks, particularly junior candidates, to include hobbies and interests on a resume to show that they are “well-rounded” or to try and be memorable.

Don’t do that. Don’t.

Hiring managers mostly don’t care what you do in your free time. If you join our team, we’ll get to know you as a person, but when interviewing you, I care about your helping us with current & future challenges, not your side interests.

Now, if your “Extracurricular” activities show abilities or skills you can highlight, they might still be worth including. Did you run a hobby organization, managing people, finances, or schedules? Did you proactively surface and spearhead something, etc? THOSE are things I might like to hear about.

But, be careful about how you frame experience related to “hot button” issues. While it can be good to highlight that you organize, run, and fund an advocacy group for [cause X], if said group’s homepage contains inflammatory statements, or your resume mentions your participation in protests that turned violent, employers may shy away from you. These can be seen as an indicator that you are an “agitator” or a PR risk for the firm. No company wants to field news questions about an employee embroiled in a legal dispute. No one will outright tell you this in your recruitment process, but some will quietly put your profile at the bottom of the pile.

Side Tip: To AI or not to AI?
Yes to both.

Yes, it’s contradictory to answer “yes” to both, that’s purposeful.

AI, or the current iteration of AI – mostly Large Language Models (LLMs) can be a useful tool in crafting and refining your resume. With that said, these are all Machine Learning data analysis algorithms, not “true AI” and are still in the early days of their lifecycle – so go into any use of them with eyes wide open about what they can and cannot do.

A few key thoughts…

DO NOT have AI write your resume and simply use it “as is” – current algos have too many limitations to make this practical.
DO USE AI to get a draft / skeleton / outline of your resume, and refine it by hand from there.
DO NOT use AI to write your cover letters, where applicable, from scratch. See a pattern here?
DO USE AI to suggest more concise or impactful wording, alternate ways to express concepts, and proofread both your resume and your cover letter(s).
DO USE AI to help find synergies between your resume and a job description, and suggest resume edits to match a JD better.

As a practical example, if you want to use something like ChatGPT, I’d recommend against going “green field” with your content, but instead put together a draft of your resume, using a structure / flow based on the advise above. Then take that, feed it into the LLM, and get suggested edits.

DO NOT TAKE THE EDITS “As-is“. Current LLMs will provide ideas that are grammatically solid, but might misrepresent facts. They also LOVE to use overly dramatic language, which can make your resume look too “sales-y” – though there is a place for impactful language, you likely know where it is better placed than a current generation language model will.

That said, current LLMs are very good at making things more succinct, suggesting alternate wording, etc- use them for this.

When levering an LLM, give it as much context as you can. Provide it your draft resume, the job description, and prompt it with the role you want it to fulfill. Tell it you want it to be a “senior talent professional, with 15 years of experience matching candidates in [field X] to impactful opportunities” or something similar. You can also give it bounds – e.g. “do not eliminate any bullets wholesale, but suggest more succinct wording.” The more you tell it what you want it to do and how to do it, the more “on target” your output.

“AI” / LLM’s can be a powerful tool, but are not an “Easy button” – use them in targeted ways, and you can increase your probability of a good outcome. But don’t get lazy – you still own your destiny here, act accordingly.

Wrap-up

*image: PixelsAway*
*Quote: Albert Einstein*

To summarize the key points we’ve made, let’s look at this from a few lenses.

Hiring Managers…

Need help solving problems
Want to augment their existing teams with the best talent they can find
Want to make the best choice in hiring someone, because onboarding / offboarding is expensive and risky
Are looking at MANY candidates, so must by nature make “quick scans” to get a probabilistic view on a potential.

As a candidate, you want to …

Show you’ve got the basic chops to do the “Base job”
Show you have delivered impact, demonstrated leadership, and have future “upside potential”
Make it easier for the hiring manager to pick you by giving them the info they need the fastest way possible.
Defeat simple machine-based scans by following basic formatting guidelines

In your resume, you should follow the principles of …

Keep it short and sweet, a page +1 per 5 – 10 years experience, with simple formatting.
Lead with what is most impactful to land the role in question
Show impact and leadership in the accomplishments you describe. Use STARS style bullets.
Filter out information that is not directly pertinent or helpful

If you follow the above, while you can’t be guaranteed a follow-up, you’ll at least be in the short list of people whose profiles get a second look, and a higher chance at that coveted phone call / initial interview.

Assuming you do get there, there’s a host more advice on interviewing and how you present yourself, but we’ll save that for another article. And even before that, there’s a wealth of information on strategy and the “hunting” aspect of “job hunting”. Stay tuned, as I expect to publish more on both topics..

What are your thoughts and experiences? Any other tips to add to the list? Disagree with anything I’m laying out here? Leave it in the comments and I’ll address from there.

Sean Reilly

career, Corporate, hiring, resume