Starting an InfoSec Career – The Megamix – Chapter 7


Chapter 7: Landing the Job

So, we’ve come this far in your infosec journey. You’ve studied hard, attended conferences, played a CTF or two, updated your resume, and networked a bit within the information security community. Great work!

Let’s prepare for your very first information security interview.


=== What to Say ===

There have been nigh infinite pieces written on the subject of interviewing, but I’d like to briefly share some basic interview skills that have really served me and my candidates well:

  • Make sure spend at least 30 minutes researching the organization you will be interviewing at. What are their strategic goals or products? Where do they have offices? What’s their corporate culture like? Consider what interests you about their mission, and how you feel you could benefit them as a security professional.
  • Always bring several printed copies of your resume and references to your interview, formatted the way you intended. HR systems will often remove formatting and line breaks before routing your resume to a hiring manager, and your copy may be more pleasant to read. You will also want a copy to reference, yourself.
  • Bring note taking materials to your interview, and make sure you’ve written down a few relevant questions to ask your interviewers about the position and the organization.
  • Arrive 15 minutes early for your interview, and be polite to everybody you meet. You never know if the person you make eye contact with and say “good morning” to in the hall will be interviewing you, later.
  • Make eye contact, and pay attention during the interview. Most of us are introverts, and this can be a challenge. Make the effort to be personable and show that you are listening to your interviewers.
  • Put your phone away and on silent. I shouldn’t have to say this.
  • Answer questions honestly. Most of my colleagues and I would very much prefer, “I’m not sure”, to an evasive answer or an outright lie, particularly on technical questions. Often, knowing where you would look something up is an okay answer to a technical question. When we ask you questions about where you could improve, there should be a real response that verifies you are a human. Everybody has some area they can improve in, and we will never believe you’re utterly perfect.
  • The initial interview is not normally the appropriate place to ask about compensation. Yes, infosec is an understaffed and in demand field. You have better chances than most at landing the job. No, your Masters in Information Security does not guarantee you the position immediately in lieu of a technical interview.
  • Do talk about your (legal) infosec-related hobbies and activities! We want to hear about the security lab you built in your house, the book you read, the CTF that you participated in, or the security related talks and projects you’re participating in. They show you are an interested and involved candidate, and a good fit for our teams.



=== What to Know ===

The previous chapters in this blog series suggested ways to build your foundational skills in the key areas of networking, systems administration, and security, so I won’t dwell too much on the necessity of knowing the fundamentals of these things such as common ports and protocols, malware types, and operating system functionality in an entry level infosec interview. Suffice to say, this is where the free educational resources, formal training, and your home lab really come into play.

You should ensure, before going to an interview, that you are up to date on the basics of current threats and security news. What you learned at your university is almost certainly not current enough for most interviews. There are a lot of great resources that provide information on ongoing threat activity. For instance, I really like the exploit kit status dashboard at (ProofPoint) EmergingThreats. SANS ISC posts botnet and scanner activity from publicly submitted data, and Sophos posts a nice free malware dashboard that shows their overview of currently detected malware. Threat trackers, coupled with the blogs, news services, and educational resources we’ve previously discussed, should enable you to go to your interview ready to answer general questions about the top threats that are currently plaguing organizations.


=== What Not to Say ===



In May, I surveyed a broad swath of security professionals to share the statements they hear from interview candidates that are the most indicative that the person is inexperienced in professional information security work. I’d like to share a few of the most popular, and why they carry that connotation. Keep in mind, the selected statements by candidates aren’t necessarily technically wrong; they more often tend to oversimplify or ignore administrative and business-related problems in security. It would be wise to choose your words diplomatically before saying any of the following things:

“Antivirus is obsolete, and a waste of money! Get rid of it.”

We can’t all be Netflix, dramatic headlines or not. It’s true that antimalware programs have a lot of problems to contend with in the 2010s. Between a cat and mouse game with well-funded malware authors, and polymorphism and regular botnet updates, simply maintaining a library of static signatures is indeed not effective anymore. Most decent antivirus vendors recognize this, and have implemented new tactics like heuristic engines and HIPS functionality to catch new variants and unknown threats. Antivirus is one component of a solid ‘defense in depth’ solution. It has a reasonable potential to mitigate a percentage of things that slip past network IPS, firewalls, web filters, attachment sandboxes, and other enterprise security solutions.

“Why are you wasting money on $x commercial product? I can do the same thing with this open source project on GitHub”

We love the philosophy and price tag on open source projects, and it’s great that commercial vendors have open source competition that drives them to improve and enhance their products. This doesn’t mean that free tools are always a viable replacement for commercial tools in an enterprise environment. There are intangible things which usually come with the purchase of a good quality commercial security product: support, regular updates, scalability, certifications, and product warranties. Those intangible things can have a tangible cost for an enterprise implementing an open source product in their stead. For instance, the organization may have to hire a full time developer to maintain and tweak the tool to their needs and scale. They may also be solely legally liable if a vulnerability in free open source software is exploited in a breach – a risk many organizations’ legal teams will simply not accept.

“They deserved to get breached because they didn’t remove Java / Flash / USB functionality / Obsolete Software…”

Most organizations exist to provide a product or service, and that’s usually not “security”. As security professionals, we’re just one small part of our organizations and their mission, and we never function in a vacuum. Oversimplified assertions like this are a dead giveaway that a candidate is not used to compromising and negotiating inside a business environment. Yes, in an ideal security world, we would use hardened operating systems with limited administrative rights and no insecure applications. Few of us actually operate in that ideal world, and many of us work at an operational scale alone that renders this unfeasible. We do what we can; navigating the political risk management game where we must to provide the most secure environment we are capable of.

“Just block China/Russia/x… IPs.”

Once again, this indicates a candidate is thinking only as a security person (and a biased security person) and not as a member of a business. Unfortunately, it also shows a lack of technical knowledge, as many attackers use large, global networks of compromised hosts to launch attacks.

“Security Awareness is a waste of money. Users will always be stupid.”

This is an appalling lack of confidence in your own ‘team’. Yes, some end users will probably always click / ignore / fail to report. (Most security people will also click when properly socially engineered.) The point of security awareness is not to create a perfect environment where nobody ever clicks on a phishing message or ignores an alert window – if your management has made that their measure of success, they’re doing security wrong. The point of security awareness is to improve awareness of threats, encourage some employees to report potential threats so you can respond, and decrease day to day problems so you can focus on the more severe ones.

“[Fortune 100] should have already have gotten rid of $OS and gone to $OTHEROS, because it’s more secure / real security people use $OTHEROS.”

This is dogmatic elitism without real business or technical foundation. Any up-to-date operating system can have a valid use case in business and in security work. A good red team or blue team security professional should be able to secure, compromise, and use tools on OSX, Linux, and Windows effectively (and indeed, there are valuable tools unique to each). It’s okay to have an operating system preference and to intelligently discuss the merits of $OperatingSystem for your specific use case. Don’t assume everybody else’s use case is the same.

“Hack them back / have the attackers arrested…”

We all crave the movie ending where the black hat hackers get their comeuppance and are thrown in jail. Unfortunately, unless we work for a LEO, the military, or a huge global telco, we’re rarely likely to get it. “Hacking back” of any sort is usually wildly illegal (especially because attacks are almost always launched from compromised hosts that belong to law-abiding people). Arrests happen when time-consuming coordinated efforts between security firms, global law enforcement, and lawyers are successful. Even the terrifying financial spearphish to your CFO is likely to not be chased down by law enforcement for some time. When permitted, absolutely do share your threat intelligence with law enforcement and working groups to aid in these important efforts. Expect any response received will take significant time.

“Don’t you monitor every brute force attempt against your perimeter? I count the dictionary attacks against my honeypot every night!”

No, monitoring this would be a waste of time in most large organizations. Behavioral trends and specific sequences of events that could indicate a compromise are more valuable to monitor. Time is money.

Any statement beginning with, “Why don’t you just…?” or “It’s simple…”

It pretty much never is that simple, so don’t personally insult your interviewer by assuming it is



This concludes the InfoSec Career Megamix! I hope you’ve enjoyed this blog series and that it has been helpful to you in furthering your own security career. Many thanks to everybody who has commented on my blogs or provided input and suggestions. Please do check out the links to other peoples’ wonderful work on the subject which I have included throughout the blogs.

[You can find the previous chapters in this blog series here:

The Fundamentals

> Education & Certifications

> Fields and Niches

Blue Team Careers in Depth

Red Team Careers in Depth

Self-Study Options]

InfoSec tickets for Veterans & Twitter Feed!

Hello all,

For the past year, I have reached out to twitter-folk for their spare and unwanted infosec con tickets they wished to donate to military veterans and military members interested in the field. I have made the decision today to formalize this into a website and twitter account, .

Why do I do this?

There is a collective misunderstanding in our society about military members. Although we may consider them to be heroes, valiant, and tough, the vast majority of charities and educational programs available to them after serving also presume them all to fit into specific blue collar professions after their enlistment or commission.

This is simply not the case. The military staffs almost every job seen in the civilian world, from cooks to network engineers. There are even infosec professionals, just like us, using similar tools and attending the same certification programs. The difference is, they are doing it on the military payscale and within military lifestyle restrictions, to benefit a larger cause.

To a junior enlisted military member working in IT or recently discharged from the military, with industry certifications and years of experience, a couple hundred dollars we might consider trivial can be an impossible roadblock to attending conferences and networking. We all know how absolutely critical attending these events can be to progressing in our careers. So why keep qualified people out over a trifling sum of money?

This Twitter account is made to reduce the isolation veterans may feel upon trying to enter the information security field. I will endeavor to RT and tweet programs beneficial to veterans and currently enlisted people,  as well as provide an informal operator service to connect people with spare infosec con tickets with veterans who want to attend the conferences.

This service will be best effort and a work in progress until I find others willing to volunteer time and effort to it. However, I believe this service fills a serious void between military and civilian IT security.

If you wish to donate a spare ticket or sponsor an attendee, please DM the account and I will relay this opportunity is available. If somebody requests the ticket, I will connect you to arrange transfer of ownership. I hold no liability for the transfer so please exercise caution and common sense.

If you are a veteran or military member who would like a ticket to a conference, please stay tuned to this twitter account and DM if you see a ticket that interests you (first come, first serve).

This service is on the honor system and I will only be spot checking military service. I can only ask for your honesty to maintain the account.

This account will not be accepting advertisement or promotional offers; corporate sponsorship for individuals is okay within reason.

[Off Topic] On Dealing with Completely Impossible Situations


Just some non-infosec-specific thoughts regarding things I’ve learned about dealing with burnout, and the really bad days:

  • Steve, Diane, Kay, Erica, Bryan, and Anna taught me that sometimes you just find family when it’s needed. (Say yes to seeing your friends, even when you’re indescribably exhausted.)
  • Jack taught me to have a breakdown plan.
  • Col E. taught me that it’s not weakness to ask for help when you really need it.
  • Rance taught me that sometimes you have to put on the chicken hat and dance besides it all.
  • D.T. taught me that you can be lying there missing a leg in the hospital, then marry your nurse.
  • Johnny taught me that even on a really crappy day, a lightsaber battle is still okay.
  • Selena taught me that writing about the worst situations can help you face them (and help other people, too).
  • Reggie taught me that however messed up things are, it’s not too late to reconcile with people you fought with honorably, like a true samurai.
  • 60 hackers confirmed that our community is real, and if you’re not a dreadful person both the “black hat” and “white hat” people in it might send cards and books to a person across the planet who needs them, without prompting or asking questions.
  • Jodi taught me be unapologetically your own self, and keep fighting and screaming at what’s wrong in the world, even when the world is beating you down.
  • Two ER visits and permanent health damage have taught me that there are repercussions for not taking care of yourself under continual and intense stress.
  • Completely impossible situations taught me that you never really know what you’re capable of dealing with until you’re faced with one. Overcoming those obstacles are the memories you keep.

I hope someday when you are going through an impossible time, you can come back to this post and find some help and hope.


The Worst InfoSec Resume, Ever

I do quite a bit of InfoSec résumé reviewing and critiquing, both personally and professionally, so I’m repeatedly asked for tips on common problems. In order to ensure that these problems were not exclusive to me, I recently had a lengthy discussion  with a number of InfoSec professionals involved in hiring (thank you!). We discussed our “top 10” pet peeves when reading candidates’ résumés.

So without further ado, here is an illustrated example of some common problems we see on many résumés, and some suggestions about how to fix them.

(If these images are hard to view on your phone or at a specific resolution, you may click them to view them full screen.)



The Top 9 Ways I Found Your ‘Secret’ Dating Profile

  1. You reused a cute username (or email address).

Aliases and usernames have become a big part of our personal online presence, and we often feel tied to them when we register for new sites and services. This can be a great was to build an online identity, but it can also make it trivial to tie our activity on various services together.

Even if your registered username isn’t immediately visible in a dating profile, it’s often visible in the URL of your profile, your profile photo filenames, or during communication with other users.

There are plenty of free and paid services which search and monitor social media and email accounts by username. Pipl is a great example. It will rapidly scan popular sites and services for email addresses, usernames, names, and phone numbers to build a comprehensive profile of a person.image002 performs a broader sweep of services for usernames only, immediately flagging services where a particular username has been registered. This is an easy way for someone with malicious intent to draw connections between a dating site profile username and your ‘real’ life, even if your profiles are correctly private or hidden.


The very simplest, a Google search will often turn up social media profiles, forum posts, and blog comments tied to a particular username. If you’re concerned about dating site matches finding your online presence, or people online finding your dating profile, just don’t reuse usernames or email addresses!


  1. You reused profile pictures.

A few years ago, image recognition on a large scale was restricted to law enforcement and corporate security. This isn’t true anymore. Free services like Tineye and Google Images will search billions of indexed images on the internet for identical or similar pictures. This isn’t necessarily traditional hash or metadata specific – cropping or resizing an image is not a foolproof way to defeat this (as I show in the screenshot below, where Tineye and Google correctly identified my profile selfie which is substantially cropped on social media). The photos are visually similar enough that the search engines’ algorithms can draw a connection.


Ultimately, this means that if you are interested in privacy, you should never reuse a photo or set of photos that you’ve used elsewhere on the internet (at any time) on your dating profile. Choose where to use your glamour shots, wisely!


  1. You forgot to check and sanitize your pictures.

Reuse isn’t the only situation in which photos can compromise your privacy. There are two sets of clues that can give away important personal information in your photos. The first are old-fashioned visual clues. Consider: is there a window in your photos, and are there identifiable buildings or landmarks outside of it? Were your photos taken in an apartment building or dorm that can be easily identified in other people’s photos? I highly recommend reading this eye-opening blog on the subject by IOActive. Give some thought to what people can see in your photos’ backgrounds before posting them to your private dating profile.

The second way your photos can betray your privacy is a bit more technical, but still terribly important to recognize. It has to do with hidden information, or ‘metadata’, which is tacked onto most pictures by phones, photo editing software, and digital cameras. You can’t see EXIF metadata without using special tools, but it may contain startling amounts of information about where the photo was taken, by whom, and when. This exists primarily to help out professional photographers and photo storage tools.


I took this pretty photo at Disney World. Let’s look at some of the data hidden inside of it:

Create Date                     : 2016:02:20 20:01:04
Make                              : Samsung
Orientation                     : Horizontal (normal)
Flash                               : No Flash
Focal Length                   : 4.3 mm
GPS Position                   : 28 deg 21′ 27.100″ N, 81 deg 33′ 29.71″ W

Even with location geotagging disabled in your camera settings, metadata still provides a tremendous amount of detail about you and your devices, and can even uniquely identify photos taken with your camera. (The use of photo editing tools also becomes blatantly obvious, which can be a cause for some embarrassment.) Ensure you remove identifying metadata from photos before posting them onto your dating profile.


  1. You forgot that the internet is forever.

If I were forced to pick only one error which causes dating site members the most personal embarrassment over the long term, it’s forgetting this. A single mistake made months earlier can haunt you. Let’s imagine that before reading this article you uploaded your professional headshot to your dating site profile. You realized a few days later that it was too much of a privacy give-away, and made the wise choice to switch to a new photo. You might not be out of the woods.

Search engines and archive sites are continually indexing as much content as they can from the internet. These sites retain cached copies of images and pages long after they are changed or erased at the original source.

Somebody with malicious intent may use this to their advantage when trying to correlate your dating profile to other web content. He or she will very likely check search engine caches for old pictures or bios that are easier to identify or contain embarrassing details. If that professional headshot is still in a cache associated with your dating profile, he or she can use Tineye to match it to your corporate bio that shares the same photograph. If you’ve changed your username, he or she may be able to find the previous version.

Unfortunately, this isn’t an easy thing to fix after the damage is done. The bottom line is: assume that anything posted to the internet is perpetual, and usually cannot be removed (even through legal action). If you post data which compromises your privacy or reputation to your profile, remove it immediately and consider starting fresh with an entirely new profile. If needed, pursue sites and search engines to remove what they can and will, and disassociate your online identity as much as possible from the content.


  1. Minor details tell a larger story about you.

This is open source intelligence 101. The individual facts and conversations you post on dating sites might not give away your identity, but as a collective whole, they may. Give some consideration to how much information you’re giving other users over time and as a whole. Did you post that you live in Milwaukee, tell a user that you live in an apartment with a pool, and tell another that you live next to an airport? These pieces of information put together say a lot more about your location than they do individually.


Pay attention to details. How much information have you posted on your profile over time as you’ve updated it? How much information are you providing in private conversations with other users?


  1. Your social media profiles aren’t private enough.

The number one open source intelligence source that people with evil intent will try to use against you, or to identify you, is your social media profiles. You make a malicious person’s life significantly more difficult by simply locking down your social media profiles so that nobody except people you know personally can view them, or that the data that is publicly visible is not enough to provide the attacker an advantage.


  1. You joined your social media profile to your dating site account.

We’ve previously discussed the privacy risk posed by sharing photos, usernames, and email addresses between your private dating profile and the rest of your online presence. Linking your social media accounts may be a simple and timesaving way to create an account on many dating sites and apps, but these sites frequently import most of the data we’ve discussed above directly into your dating profile and account. Given all the points we’ve discussed previously, this is obviously not a wise choice.

I highly recommend using an entirely new and separate email account to sign up for a private dating profile. If the site in question absolutely requires linking a social media account, start a new one without unnecessary personal details.


  1. You forgot that social engineering (and catfishing) happen, and can happen to you.

No matter who you are, which gender you are, what you do for a living, or how much money you make, you can be a target for fraud or social engineering. Somebody who wants to manipulate or identify you on a dating site may attempt to gain your trust before drawing you into a trap. If something doesn’t feel right, it probably isn’t. If something seems too good to be true, it probably is. Be very cognizant of members leading you into revealing unusual personal details, compromising photos, or financial information. Dating sites are fair game to cyber-criminals.


  1. You weren’t aware that you were accepting risk.

Dating online, like the rest of our lives, carries some inherent risk. The level of risk associated with joining a dating site and interacting with others on that site varies by each individual’s situation. For example, this risk may be to your reputation if your profile (or behavior with other users) were publicized, or to your personal safety if your location or identity were compromised.

Online dating is a great option for many people and many healthy relationships exist today because of it. You must simply consider what level of risk you’re willing to accept before doing it. Even if you are meticulous in protecting your online presence, there will always be circumstances outside your control. What would the consequences be if the site were breached, and your identity and interactions were posted online or sent to your employer or family? If somebody successfully identified you, how easy would it be to find your street address or place of business? Like any other activity that carries some significant risk, you must consider these types of questions and make your own informed decision.

Bad Security Product Warning Signs: Part 1


Starting an InfoSec Career – The Megamix – Chapter 6

[You can find the previous chapters in this continuing blog series here:
Starting an InfoSec Career – The Megamix – Chapters 1-3
Starting an InfoSec Career – The Megamix – Chapters 4-5]

Chapter 6: Self-Study Options

In the previous chapters, I’ve discussed potential career paths, education and certification options, and the fundamental knowledge needed to become a successful InfoSec professional. Unfortunately, college degrees and certification courses aren’t financially or logistically an option for everyone, nor do they provide all of the skills and practical experience needed to become a desirable candidate for an entry level position. Without further ado, let’s delve into some options for improving InfoSec knowledge individually.

==== Home Labs ====

Building a home practice lab is an integral part of improving skill at any area of blue team or red team information security. Since most of us (hopefully) don’t want to break the law and get arrested while learning how to hack, conduct forensic investigations, or reverse engineer systems, we’re obliged to create our own self-contained network environments to practice and learn within. This will also improve network and systems administration skills, which as I noted in Chapter 1 are absolutely fundamental for being a well-rounded InfoSec professional.

A decade ago, a home lab looked significantly different. It almost certainly included multiple computers, and likely a network rack complete with switches, power supplies, KVM, and cabling. While this is still a great option, a rack of computer equipment is noisy, hot, and power consuming. Today, we have the tremendous luxury of virtualization. A single reasonably spec’ed ESXi host server can act as most of our practice environment. While we might still opt for some physical network hardware, we have virtualized network lab environments available for use, as well. I really prefer the virtualized option because as we exploit, infect, and otherwise destroy our hosts, we can simply revert them to an earlier snapshot and start over.

Regarding purchasing the physical equipment or host machine(s), we can get as creative as our budget requires. A great way to purchase server grade computer hardware is via federal and state government auctions. These auctions are fairly underutilized next to commercial sites like eBay, and can offer some great deals during regular equipment replacement schedules. Remember that local businesses, hospitals, and municipal services often replace their hardware and sell the older equipment for a fraction of the original price. For virtualization, we’ll want a decent server grade processor, a lot of memory, and enough disk space for all the operating systems we are interested in using to grow as expected. Everything else is fairly negotiable. Many folks buy a few old servers of the same model, pull all of the memory, NICs, and hard drives out, and put them into one chassis.

The hosts we install in our lab environment shall vary quite a bit based upon our area of interest and what we’re currently trying to accomplish. For instance, in my forensics lab, I selected SIFT and Windows 8 hosts which I use to conduct analysis, and an array of primarily client OSes which I conduct analysis upon. My network monitoring and incident response environment is very different, because network services, network IPS, and firewalls are in play in a more realistic network environment. A penetration testing environment will look different still. Before you purchase equipment or begin the lengthy process of building your lab, consider what you want to learn, and what hosts and services you will need to accomplish this goal.

I’m not going to delve much further into the technical details of building out a lab, as a lot of people have done great writing on this subject already. I recommend looking at Carlos Perez, Matt Barrett, and Adrian Crenshaw’s informative blogs.

==== Self-Study Materials ====

Every person has a different learning style. Some of us are more comfortable learning new skills by watching a video; others need hands on practice or reading materials to understand new concepts best. Fortunately, at this point people who wish to learn InfoSec skills have a plethora of freely available options to fit any learning styles.

For the Visual Learner:

Years of talks at information security conferences have been recorded and are freely available on YouTube. I’d avoid watching Joe from ACME computer shop explaining how to use Kali, but there are more hours of recorded talks on from reputable conferences than anyone will ever have time to watch. hosts an immense number of conference talks. Adrian Crenshaw has recorded talks at conferences for years, and has a prolific archive of these videos on his channel. SecurityTube is also a great resource, (although some of their materials are paywalled by PenTester Academy, which may or may not be in your budget).

For the Auditory Learner:

Check out the amazing range of InfoSec podcasts available for free. There are so many more great podcasts than I could discuss in a blog of their own, but some highlights are PaulDotCom, Southern Fried Security Podcast, Security Now, ISC Stormcast, Defensive Security, Liquidmatrix, and Braeking Down.

For the Reading Learner:

There are two major resources you should investigate – textbooks, and blogs. This will, of course, vary quite a bit based your area of interest. My personal ‘essential reading list’ for Information Security professionals would include the following:

There are an immense number of amazing security blogs out there, but a very short list of my favorites includes Dark Reading,  Krebs on Security,  McGrew Security, Graham Cluley, Naked Security, Lenny Zeltser, Troy HuntAndrew Hay,  Threatpost,  and Andy Ellis.

For the Kinesthetic Learner:

As we previously discussed, a home lab is a great option, followed by Capture the Flag exercises and Challenges, which I discuss in the next section.

==== Capture the Flag and Challenges ====

Once you feel ready to leave the safety of your own home lab and delve into another network, a great option is Capture the Flag events, and similar challenges. A large percentage of hacking conferences provide some kind of CTF event, which will pit your skills against challenges they’ve designed as well as other participants, in a structured, legal environment. The challenges usually vary from simple to extremely difficult, and points are awarded to participants as they find or reach ‘flags’ hidden in the challenges. Don’t be daunted; most CTF events are rarely restricted by skill level, and they’re a great way to test what you’ve learned. You’re competing against yourself as much as other teams or participants.

CTFs and challenges are not restricted to red team penetration testers. There are plenty of open and paid practice challenges in many areas available now, both in person and online. DFIR challenges test investigation and forensics skills, while malware challenges test participants’ ability to reverse and analyze malicious code. Check out the great list of online challenges at

==== Conferences ====

There are no substitutes for in-person networking or training events. I strongly recommend attending InfoSec / hacking conferences, but I also encourage you to choose the right ones for you. Regrettably, the events with the biggest budgets often get the most hype. That does not translate to them being the best environments to learn in. Cost is often a factor that bears consideration, as well. Tickets to InfoSec conferences range from free (or nearly free) to thousands of dollars. Hotel and airfare costs vary by venue. All these factors should weigh into your decisions, but there’s a conference for everybody.

Hacking conference size and content vary a lot, but there are some commonalities. There are normally one or more tracks of speaker talks, selected by the organizers from outside call-for-paper submissions. Capture the Flag type events are fairly ubiquitous. It’s also not uncommon to see an option for longer, hands-on training classes for an additional fee. You’re likely to see some vendors, as well as hobbyist groups such as locksport organizations or makerspaces sharing their expertise. Evening parties sponsored by the conferences or vendors can provide an opportunity to network and have fun.

Let’s discuss a few popular conferences. A couple caveats. Firstly, I’m quite certain I am going to offend one conference or another by not listing them here – for this list I selected some better known representative examples and it is by no means comprehensive. Secondly, I’m based in the US, so my examples are primarily in North America. Hacking/InfoSec conferences are a global phenomenon, and the types of conferences I list have equivalents in Asia, Europe, Africa, and South America. Please feel free to ask me for assistance in finding ones in other locations as needed.

DEF CON – Las Vegas, NV, USA

One of the oldest, most famous, and largest hacking conventions in the world, DEF CON is held in August on the Las Vegas strip. The attendees are a mix of everybody from the most dubious black hats to corporate security professionals, from journalists to Generals, from researchers to federal agents. Events and talks run the full gambit in every sense of the word. The parties are wild and so are the attendees. DEF CON tickets current cost $230, (cash only!).

>> Pros: This is where you’ll see some of the most cutting edge research released, and meet many top notch pros. Everybody should DEF CON at least once, for the sheer experience.

>> Cons: Over-the-top parties, crowds, and hangovers can overwhelm actual learning and networking. If this is your first hacking conference, or you’re not reasonably cautious, you may be targeted for pranks (or worse).


Black Hat (USA) occurs the week prior to DEF CON, and offers more structured training opportunities on a variety of topics. There’s a heavy vendor presence. Black Hat is more targeted towards security professionals and executives, and offers organized networking events and a bevy of courses and high profile speakers. The talks are well vetted. This doesn’t come cheap; regular tickets are currently $2195. Training courses cost significantly more. If money is a factor, I certainly wouldn’t recommend paying your own way to Black Hat unless there is a course you desperately want to take that isn’t offered anywhere else. Wait for a scholarship or corporate sponsor.

DERBYCON – Louisville, KY, USA

DerbyCon is a relatively new but very popular conference, and acts a bit like a more community and family-friendly alternative to DEF CON. It occurs in September in the heart of downtown Louisville. While it’s not as big of a conference, DerbyCon offers five simultaneous talk tracks, as well as hosting a few special interest working groups and CTF. DerbyCon tickets are $175, and given the reasonable cost of living in Lousiville, this can be a pretty economical conference, without quite as much of the shock value. Although there are bad apples at any hacking conference and basic precautions should always be taken by attendees, DerbyCon is policed pretty well and is a very safe bet for a first con.

SHMOOCON – Washington DC, USA

Shmoocon was founded by a husband and wife team to become a relatively small, friendly, community and education focused conference. It occurs in January, and costs $150, making it the most affordable of the ‘big name con’ admissions. Due to its location and educational reputation, it’s popular with federal government, military, and federal contractors, and the networking, vendors, and talks can reflect this a bit. The downside is that Shmoocon has grown much more popular than its size allows, and tickets sell out quickly – very quickly – a matter of seconds, making attendance a bit of a lottery. If you plan to attend Shmoocon, (I do recommend it), read up on the ticket purchase process well ahead of time.


If you missed that RSA occurs in February, you’re not tuned into information security news. I can draw a lot of parallels between RSA Conf and BlackHat, but personally favor Black Hat as an event. They’re both targeted at executives and professionals, throw star-studded vendor parties, come with a hefty price tag (standard RSA tickets are currently $2,295), and get plenty of press. They have the biggest vendor expos, and often boast high profile speakers. I don’t recommend RSA to entry level infosec folks, even if the price tag is in your budget. For the money, I’d attend a course at Black Hat or REcon. The glitz and glamour do not make this the best environment to learn fundamentals or network, and despite some very good speakers, in my opinion RSA Conf continually commits public security faux pas to the ire of hackers and security professionals.

RECON – Montreal, QB, Canada

If reverse engineering malware, hardware, or software is your cup of tea, there’s no better conference to learn more than REcon, which focuses exclusively on sophisticated reversing. Ticket prices for RECon increase through the year leading up to the event, currently starting at 700 CAD and culminating in 1200 CAD in June. Student tickets are discounted. The ticket price is hefty, but includes snacks and lunches. The available hands-on training courses will run you around 2000 – 5000 CAD, so once again, you may want to wait until you’re eligible for some sort of sponsorship for this one. I have not had the pleasure of attending this conference myself, but I’ve heard nothing but glowing reviews from my colleagues in this space.

CIRCLE CITY CON – Indianapolis, IN, USA

Circle City Con is newer than Shmoocon and DerbyCon, but fills the same educational / community friendly conference niche. Circle City Con occurs in June, near the Indianapolis Convention Center. Tickets are currently $150 and include optional training classes, aside from any required materials. Circle City Con is another safe bet for a first conference, and for family participation.


Hackers On Planet Earth is still a bit of a ‘hidden gem’. Although it’s one of the oldest annual hacking cons, it remains reasonably small and attended by industry greats. HOPE occurs in July, and tickets are currently $150. HOPE offers some of the most unique and varied events of any conference outside DEF CON, and boasts film festivals, art, and robotics along with the usual offerings. It’s a bit more eclectic and nuanced than other conferences. HOPE is worth serious consideration, especially for East Coast folks.

GRRCON – Grand Rapids, MI, USA

GrrCON specifically states their goal of avoiding elitism, and as a result they’ve earned a reputation as a positive and friendly environment which is heavily geared towards great networking and security education. GrrCON occurs in October and regular tickets are currently $150. Another location with very reasonable room and board, it would be a great choice for a first con. GrrCON also offers opportunities for family participation.


Perhaps you looked at this long list of conferences, and balked at the locations, travel costs, and ticket prices. All is not lost. Seek out your local BSides event, which occur in many metropolitan areas. BSides events tend to be organized by local hacker groups, and most are one or occasionally two days. BSides also tend to be smaller and less expensive, with tickets usually ranging from $0-50. There’s rarely a good excuse to miss your local BSides – it’s a great opportunity to network with security folks in your area for a nominal fee. BSides events also make a great excuse to travel to cities on your bucket list across the world, learn about hacking, network with people, while enjoying the local culture, sights, and cuisine.

I’d be remiss if I did not briefly discuss hacking conference safety and preparedness. As I’ve mentioned above, the level of ‘threat’ at conferences varies and exists everywhere, but regardless of the event you should take common sense precautions. (All of these precautions should translate into everyday life, because bad gals and bad guys are everywhere!)

  • Consider whether it is necessary for you to even bring a laptop to the conference if you’re not attending a course that requires one. Given insecure networks full of hackers, safely using a laptop adds an extra layer of preparation required and gives you another bulky, expensive item to carry and keep track of.
  • If you must bring a laptop, I highly recommend using a new hard drive with a clean OS image, full disk encryption, and as little personal data as possible that you only use for the conference(s). Ensure you have a standard array of vetted security tools if you plan to connect to any network, including VPN. Ensure wireless and Bluetooth are fully disabled when not in use. Use common sense about what you log into.
  •  It’s hard to function today without a smartphone, but consider ways to make your phone more secure. Burner phones or faraday bags are popular options. At the very least, ensure wireless and Bluetooth are off, and that the phone itself is encrypted. VPN if possible. Do not connect to WIFI. Do not borrow phone chargers.
  • Bring cash for as many purchases as possible. Bring as few credit/debit cards as absolutely necessary, and ensure they’re in a vetted RFID safe wallet (but certainly don’t expect those to be foolproof). Don’t bring unnecessary stuff in your wallet or purse such as your work ID, social security card, or passport. Do not use an ATM within an easy walk of the event. I have rarely been to a conference where the hotel ATM wasn’t obviously and amusingly hacked by the end of the first day.
  • Don’t leave valuables unattended at the bar or in your hotel room, in a hotel full of hackers who can trivially open (any) hotel doors. Double lock your room when you’re inside.
  • Know who you can contact and how to reach them if there’s a security or medical issue at the conference – most hacking cons have a staff of security ‘goons’ who are always present and reachable. Any large event can have its share of bad apples, rowdiness, alcohol overuse, and drugs, and they’re there to keep things from getting out of hand. That being said, hacking conferences should not be treated like Mos Eisley cantina. Look out for the safety and well being of your friends and the people around you, and get them help if needed.

==== Local Hacking Meet-ups ====

Aside from organized conferences, many metropolitan and regional areas have formed hacking meet-ups of varying structure and activeness. I recommend finding your local group as soon as possible and participating as much as you can, as it’s a really important way to network with local hiring managers and security teams. Name recognition in this community is absolutely invaluable when applying for jobs.

There were ways that hackers met two decades ago that still work, but they’ve been  impacted by Web 2.0 and social media as much as anything else. So, I’ll both discuss the more traditional ways to find your local hacker and InfoSec folk, as well as newer options.

The Old Ways

  • DEF CON local groups: They’re named by area code, globally. Unfortunately, in my experience, some are now defunct or inactive. (Check and make sure before showing up.)
  •  2600 : 2600 meetings occur in public spaces to be inclusive to everybody, but be cognizant that they are more ‘hacker’ meetings than ‘information security’ meetings. Their active group list is maintained pretty well.
  • CitySec meetups: A more ‘security professional’ focused set of informal meetings in many global metropolitan areas.

The New Ways

  • I’ve seen quite a few various information security organizations start posting their meetings through this site over the last few years. It’s always worth a look.
  • ISSA: A formal professional organization with chapters around the world.
  • Twitter – Plenty of these organizations post their scheduled events.
  • LinkedIn – Plenty of these organizations are listed as LinkedIn Groups.



Hair Dryers, Hacking, and Us

In case you’ve been living under a rock for the past several days, IBM posted, then ultimately removed a video promoting STEM fields for women via “hacking hairdryers”, to a great deal of public outcry from STEM professionals. The unhappiness stemmed not only from perceived sexism, but also tremendously poor timing as the ad was released close to the anniversary of the École Polytechnique massacre of 1989.

I will apologize from momentarily veering away from my usual structured technical guides. However, I’d likely to briefly state my own experience and thoughts on the matter, because I feel there are a couple things that still need to be said.

Before I continue, I’d like to make it clear that I see no purpose in badmouthing IBM further regarding their campaign. I genuinely believe they meant well, and I have many exceptional friends (both male and female) employed in STEM fields there. I’m not offended by their campaign; I merely feel disappointment. The ad (probably generated by an unrelated advertising team) was symptomatic of what I perceive as a systemic misconception about how to interest girls and women (and in a larger sense, minorities) in STEM fields.

I’m fairly straightforward about my interests and experience on social media and my blog. I hope I have properly expressed over the years that I truly have keen interest and skill in an array of tech, without compromise. Tech isn’t merely a career for me – it’s something I live. I also publicly enjoy a fair number of things that are often traditionally categorized as ‘feminine’. I own a gratuitous amount of makeup. I enjoy subversively playing with the ‘sparkly’ and ‘pink’ tropes. I will admit that it took time for me to reconcile these things as a young adult. These things are not mutually exclusive, nor are they particularly interrelated apart from my persona.

I’m not a girl hacker – I’m a hacker. I am not a hacker because somebody taught me to hack on a pink keyboard. I learned to hack, code, and solder the same way most everyone else did. I don’t personally know any female hackers or technical professionals who state that they owe particular success or interest to being approached with anything pink, sparkly, or remotely associated with Barbie. Your mileage may vary.

I owe my skill at tech not to campaigns targeted at me as a girl, but to the fact that by the time that people told me that I could not do things because I was female I was already confident in my ability to do them. By the time my sixth grade science teacher reminded me to, “Remember what happened to Joan of Arc”, I had coded my first text based RPG and soldered circuit boards, and I had found that it was something I enjoyed.

My parents never gave me any presumption of advantage or disadvantage in life to being female. It had no bearing. There was an expectation that I would learn to play a musical instrument and appreciate fine arts, but also help fix the car or TV when they broke and have a solid fundamental understanding of science. My parents both firmly held the assumption these were things an informed human being should do. If I showed an interest in something beneficial, they encouraged it.

Outside of my immediate family, who I firmly believe were instrumental in me freely pursuing an interest in a variety of fields, I also can point directly to youth organizations like the Girl Scouts. Although I can absolutely name cases where I’ve seen them stoop to the same fallacy, even in the 80’s and 90’s, their youth programs still offered a wide array of science and tech teaching that was presented in a great, unbiased, non-condescending way. Our telescopes never needed to be sparkly. We just had to know that we were looking at Saturn through the eyepiece in a cramped observatory on a chilly night, and that was enough.

In my experience it’s absolutely an unfortunate reality that women and girls often do face negative pressures, preconceptions, and lack of encouragement from many sources when they demonstrate any real interest in science, technology, engineering, or mathematics. Trying to advertise these fields through gross gender stereotypes is probably not the way to fix this problem. The ability to excel comes from being told it’s OK to pursue almost any interest by the formative people in a child’s life. This includes family, teachers, mentors, and the community. It comes from being provided exposure to varied interests at a young age. We have to counter the societal negative pressures with positive encouragement for everybody.

Give the kids and young adults in your life the exposure and support to explore and pursue things they wish to.

Get involved with the many great organizations like Hak4Kids and DefCon Kids that provide so much education and motivation to youths.

If you’re able, mentor and sponsor people in your community who don’t have support to grow and learn in tech fields.

Resume Reviews for Veterans

Hello all,

A brief reminder, if you are a veteran and considering a career in infosec, please reach out to me this week and I will happily review your resume and provide suggestions and comments.

I post this around Veteran’s Day because I usually receive an overwhelming number to handle on my own. I do help people who ask as I can throughout the year.

I will also be tweeting similar offers from other people in infosec, as well as friends in related fields, so please keep an eye on my feed.

Thank you for your service,



Starting an InfoSec Career – The Megamix – Chapters 4-5

Chapter 4: Blue Team Careers

With the help of many people in InfoSec who kindly gave me advice and quotes, I have created a perhaps overly simplistic listing of common InfoSec roles in today’s market.

For each role I have listed a brief summary of what the job does, where these jobs can be found in the (primarily US) workforce, some suggestions for breaking into the role, as well as some common misconceptions about it. I also requested a person who currently works in each of the roles to provide me a brief quote on how they reached this point in their career and what is enjoyable about their role. Immense thanks to everybody who helped. You should follow all of these peoples’ fantastic feeds.

As a caveat, many of these roles are somewhat simplified and condensed. This is an overview, and this chapter could go on much further (and perhaps it will in the future). It is intended to give people new to the field a brief explanation of the types of jobs that we do as InfoSec professionals.

[If you currently work in one of these fields and wish to contribute an additional quote or comment, please DM me on Twitter @hacks4pancakes and I will do my best to accommodate you if possible, in a timely manner.]


 What this job does:

Today, work in a Security Operations Center is a very common entry point into Blue Team InfoSec roles. Entry-level Security Analysts (or SOC Analysts) frequently do shift work in around the clock monitoring centers, monitoring security logs, responding to SIEM events, and performing security ticket handling. In a good work environment, this role should give the analysts a solid foundation in InfoSec work to move on into a more specialized role in one to three years.

Where are the jobs:

Managed security vendors, and medium to large organizations and agencies.

What gives a candidate an edge:

Showing keen outside interest and involvement in InfoSec (especially on the resume). Good certifications to have are Security+, Network+, or GSEC. Degrees are a plus.

Avoid this trap:

Ticket farms with no opportunity to learn. A good analyst role will offer formal and informal training and the opportunity to gain certifications as part of the position. It will also clearly offer the analysts the opportunity to shadow and cross train across multiple roles.

Personal career story:

“Trained as a psychologist. Worked through school in IT. Spent 20+ years doing sysadmin/etc., before there were dedicated security positions. It was just part of the job. Refocused last year, decided I wanted a dedicated security position. Interviewed at several employers, got offers from all. Wound up as an analyst with CERT/CC. Interest, passion, and relevant (but not direct, paid, titled experience) pays off.”


 What this job does:

Forensic analysts are best known for recovering hidden and deleted data from hard drives, but today the role often includes lots of memory, mobile device, and network forensics. As opposed to ediscovery roles where forensics is limited to recovering evidence to be used in legal proceedings, on the security side, forensic analysts make up half of the “DFIR” team and figure out and report how digital devices were compromised, infected, or abused.

Where are the jobs:

Managed security vendors who provide DFIR services, medium to large organizations and agencies, computer crime investigative services.

What gives a candidate an edge:

Curiosity and a drive to investigate. A solid understanding of how operating systems, hard drives, and memory function extremely helpful. Forensic tools are fairly specialized, so exposure to commercial tools like AccessData FTK and Guidance EnCase are a plus if possible (they’re expensive). Memory forensics is woefully under taught in forensics degree programs and is now nearly a requirement, but the associated tools are generally free (such as Volatility Framework, Rekall Framework, and Mandiant RedLine). Good certifications to have are GCFE, ENCE, GCFA, GCNA. Most of the vendors named above provide formal training programs on their products.

Avoid this trap:

Believing the hype about steganography. Even law enforcement rarely sees it. But I’ve seen it as a senior capstone or conference talk subject more times than I can count. Forensics is not CSI: Cyber. It is painstaking, time consuming work, often involving hours of reading through file indices.

Personal career story:

“I started coding at a very young age, but I quickly realized my passion was at a lower level on systems, from computer hardware to the operating system. My interest in forensics was piqued as a teen when I read a Popular Electronics article on hard drive function and data recovery. I read all the (3) books that existed on the topic at the time and decided I desperately wanted to become a computer forensic examiner. Unfortunately, at the time, it was a very rare career that was not taught in universities. After many failed attempts to network inside the law enforcement forensics field, I started applying for entry level jobs. This seemed impossible after many discouraging interviews because I had no hands on experience with the expensive corporate forensics tools. However, I was still involved in the hacking community, and a friend of a friend eventually got me a security analyst job that allowed me the necessary experience with critical tools to move on into a forensics heavy role.  The best part of my job is starting with nothing but evidence, sifting through it, and building a story of what happened on the device until conclusions can be drawn.”


What this job does:

The other half of the “DFIR” team. When a breach or major security event occurs, this person coordinates the response and recovery teams, establishes a timeline of what happened, and figures out how to respond to it with the aid of other security roles, management, lawyers, and IT. Incidents can vary from data breaches to malware outbreaks, to phishing or APT response.

Where are the jobs:

Medium to large organizations, security contractors who provide DFIR services.

What gives a candidate an edge:

This job requires good analytical, organizational, and communication skills. Candidates need to be able to work well under high pressure and high stress situations at odd hours. This is not a job for people who don’t like to manage a project or a team, or report to senior leadership. Good certifications to have are GCIH and CISSP.

Avoid this trap:

Taking an incident response role when you aren’t comfortable taking charge and maintaining control of a situation, or writing extensive formal reports. You must have self-confidence and leadership skills to fulfill this role.

Personal career story:

“I used to work for a major shipping company. I hated the work. I’d do 60 hour weeks at weird hours and was unable to advance because of degree requirements.

I had an acquaintance that I played golf with that offered to float my resume around since he knew I had some technical skills. It took about a year before I heard back from him about a job.

He called me up one day to ask if I was still interested in working for him. I’d be writing tech policy and assisting with certification and accreditation work.

It was there that I learned I was making crap policy and had no clue if what I was writing had any sort of basis in reality. No one could tell me how any of the systems worked or if what I was writing would even be effective.

So I started looking into learning this stuff for myself. I stated teaching myself the anatomy of breach and what to look for during an intrusion event. The quality of my policy went up. It wasn’t overly restrictive but provided the required level of security. It started to get noticed.

After that, I was invited to help with network architecture on a small project. Again, I had to teach myself everything but I was working with more experienced people that loved the work I was doing.

Eventually that project ended and I was looking for work. It was only then that I fully got my start in info sec. I was hired to do enterprise security appliance integration. Take a SIEM and integrate it into a client environment.”

Personal career story:

“I got into infosec my moving laterally through related jobs. I’d built some websites as a hobby, so I got a job doing web programming. I entered the US Cyber Challenge and made contacts that let me get into QA at a security company, which let me play with malware and the like. From there, I was able to move to a security role at a fourth-tier social network, and from there to SOC work at Mandiant.

Key features that helped me was self-driven training, finding jobs that included things that I could do and things that I wanted to do, and hitting up the types of companies that were willing to take a chance on someone with low experience and drive to learn.

What I like about IR is how things are constantly changing. I’m always researching, exploring, learning. Always new challenges”


What this job does:

Malware analysts figure out the nuts and bolts of how malware, adware, and hacking tools work, what their capabilities are, write signatures for them, and may attribute them to a campaign. They perform live, or heuristic analysis (meaning they run the malware in a sandbox and carefully analyze system changes and traffic), and static analysis of the code itself (which may be written, hidden, and packed in a way that purposefully makes this very confusing and time consuming.

Where are the jobs:

Larger organizations, cybercrime investigation agencies, antivirus and malware research firms.

What gives a candidate an edge:

Strong programming skills, especially scripting and assembly code. Strong network traffic analysis skills (you’ll be identifying and decoding lots of malware traffic). Experience with sysinternals tools and equivalent. Excellent analytical skills, and lots of patience. Good certifications to have are GREM or CREST CMRE. Previous exposure to writing IDS or Yara signatures may be useful.

Avoid this trap:

Assuming malware analysis is entirely heuristic or signature-based. Sandboxing alone is not adequate. You should understand assembly and programming architecture well in advance to succeed at this job.

Personal career story:

“So I figure I’d add my experience for breaking in to infosec. My background is in datacenter operations. I was a former sysadmin. My break into information security was knowing how systems work and studying for certifications to demonstrate that I had foundational knowledge enough for someone to take a risk on me. My key to success was to never stop putting myself out there and never stop submitting my resume. I know it seems lazy and banal, but study and persistence paid off for me.”


What this job does:

Security engineers are what most people think of when they hear that somebody works in network security, but today the job goes far beyond firewall management. They manage and update security appliances and rulesets. They may also keep data storage, tools, and log feeds working and useful for the other security roles listed. In today’s security world, they’re usually the people who manage SIEMs and security log aggregation tools. Sometimes security engineers are even responsible for scripting new tools and API integrations.

Where are the jobs:

Today, most organizations and agencies (that do not outsource these tasks) keep security engineers or system administrators with security engineering experience on staff.

What gives a candidate an edge:

Excellent systems administration skills, in Windows, CentOS, and Linux. Strong scripting skills (such as Python or Ruby). A general knowledge of security operations, practices, and applications. Certifications and training will vary by the specific position, as security engineering roles can specialize further. Some examples are SIEM and security appliance specific training through applicable companies like Cisco, Splunk, RSA Netwitness, Juniper, Blue Coat, Palo Alto, or HP ArcSight.

Avoid this trap:

Becoming too tied to a single platform or vendor. Falling for the ‘magic black security box’ sales pitch by a vendor without proper research. Avoiding open source tools entirely, or conversely, avoiding commercial tools entirely.

Personal career story:

“I broke into infosec because I have been interested in the field since reading “Cyberpunk: outlaws and hackers on the computer frontier” in 1991 and 20 years later I found myself working on an Internet of Things project in the same office as the guy who ran the Security team. We had lots of great security-related chats and one day I asked him: “hey, I’m interested in getting into security, can I join your team?”. He said: “Sure!” and the rest is history!🙂 Being in the right place at the right time made all the difference.”


What this job does:

Security auditors and compliance staff evaluate and rate security programs and check organizations’ compliance with local, national, and international laws and standards. These standards can be required by law or merely ones that the organization chooses to strive for. For example, in the US, required standards include PCI for payment processors or HIPAA for medical records storage. Most formal security standards have regularly scheduled formal and informal inspections of documentation and procedures. Auditing and compliance staff perform these inspections, ensure compliance and improvement, and report their findings to leadership or regulatory agencies as required.

Where are the jobs:

Medium to large businesses, regulatory agencies, contract-based auditing firms.

What gives a candidate an edge:

Excellent organizational and report-writing skills. The ability to communicate courteously and diplomatically with all levels of an organization. Specific knowledge of applicable standards. Good certifications to have depend on the situation, For instance, the PCI Security Standards Council offers their own assessor certification.

Avoid this trap:

Assuming these jobs aren’t technical or demanding. In fact, many of these jobs require lots of travel (for on-site inspections), and a solid working knowledge of a wide array of security devices and concepts.

Personal career story:

“Being an effective Auditor can be one of the most rewarding and visible positions within an organization as your work product makes it in front of all levels of management up to the board of directors and is based on: evidence (policy and process), legal fact (regulation or policy mandated standard), and verification through security testing. The core of all IT Audits is controls and residual risk. If you enjoy technical challenges, making well formed evidence based (legal) arguments, and enjoy reading legalese then you’ll love Auditing.

I started out as a UNIX/Linux Systems Administrator in the early 90’s and learned how much I didn’t know after reading through the Rainbow Series ([0],[1]) which I obtained after reading the alt.2600 Usenet FAQ, making what I thought was a prank call to the National Computer Security Center requesting a copy of the series. Surprisingly, the operator was happy to send me the series and they arrived a couple weeks later giving me an encyclopedia of material to read. After reading through the series, I became interested in other standards
such as ISO 17799 (Security Techniques) and 15408 (Common Criteria) and the NIST 800 series (Computer Security Guidelines), and became infatuated with evidence and investigations.

These two interests: standards and investigations, became my foundation for becoming an Auditor. After my first gigs as an IT Auditor I quickly learned that organizations would try to fake their way through an audit
so I applied my systems administrator knowledge and learned how to exploit systems after being told during a final presentation of findings that a control was in place that I knew was not applied. So, during the meeting I demonstrated the exploit I’d used to verify the lack of patching.

I soon learned exploiting things to provide controls weren’t in place was Red Teaming or Penetration Testing, which I see as a variant of IT Auditing – proving controls are not in place. Later, during a Penetration Test I’d discover that a system was already compromised and that would move me into digital forensics and incident response.”


What this job does:

Threat researchers study attackers and their methods, and try to quantify their tools, tactics, and procedures (TTPs). This means observing and reading reports of attacks, and not only identifying ways to better detect the attackers, but attempting to predict their next moves based on behavior or world events. In some situations, threat intelligence analysts may also be asked to attempt attribution of attacks to a specific organization or country.

Where are the jobs:

Large organizations, cybercrime investigation, threat research firms

What gives a candidate an edge:

This is one of the backgrounds that is harder to obtain. Many of the best threat intelligence analysts were prior government or military intelligence staff and were formally trained as such. In lieu of this, a strong background in political science, foreign languages, or international relations along with strong security analysis skills can be useful. As one would expect, good report writing skills are a must.

Avoid this trap:

Relying only on open source feeds of intelligence data. A good threat analyst is regularly identifying who might target their organization or customer based on current events, industry, or high value targets in their environment.

Personal career story:

“I don’t have a comp sci degree or tech certs but I’ve been slowly working on them via EdX. My interest ignited when I read an online newsletter by Kaspersky. I didn’t know what half of it meant but it mentioned Stuxnet. The concept of nation state threat actors, tailored viruses, etc had me hooked and I went searching Google to learn more. But things really happened when I went on Twitter and literally fell down the rabbit hole that is InfoSec. I haven’t come back out. Everywhere I looked there was a link to learn something. I started by reading all the online content I could. And discovered online learning for free. Then, I read the bios of people I admired to see what their skills and advice were, and got up my nerve to ask questions. I followed the guys on Twitter who were finding stuff live and reporting it. I asked questions, and looked up what I didn’t know. I value beyond words my network of friends now on Twitter. The world opened up. As well, I made my own blog to share info at the ground level because I understood to well how it feels not to “get it”. When Shellshock/Bash hit, I became the go-to person in our office. From there, I launched a weekly team security briefing, and posted that news to share with clients on our sites. From there, I pushed for the security analyst/researcher role in my company. And I’ve carefully drafted a security plan we will roll out to our clients based on the wealth of knowledge I found from my resources here in InfoSec.

My strengths were more communications and learning, so I played to those to build up technical knowledge. And I was asked to contribute to online blogs, which was very gratifying. I could learn and contribute to this community! Perhaps the most amazing experience has been attending Cons. They inspired my blog about the learning and community that happens when we get to do face to face time. I listen carefully to where needs are, to look for where I can share my skills or knowledge. Or where there is an area needing more people to grow their skills. Currently, I’m working on becoming our key resource on Cloud Security, and pursuing a niche interest in Mainframe security.

I love the people I’ve met, that learning is everywhere, and that the work we do really matters. Everyday we make a difference. This is all I could ever want.”


What this job does:

Finally, we get to the directors and executives of the security space. This is rarely a ‘breaking in’ point for people new to infosec, but it occasionally happens as skilled people in other areas of technology or policy management are picked to lead security programs and groups. These folks develop and maintain the fundamental security posture and procedure for their organizations, taking into account international law, industry standards, and corporate requirements.

Where are the jobs:

Most organizations of moderate or large size, particularly government and those which deal with sensitive data.

What gives a candidate an edge:

Extensive experience in managing resources and people, solid understanding of a broad range of IT concepts including security.

Avoid this trap:

Losing touch with the information security community whilst relying on vendors or agencies for critical news. The fastest way to know what is going on in the security space is to attend hacking conferences, watch social media and blogs, and participate in research and training. I can’t count the times I’ve met a governance executive who still thinks Def Con and its ilk are made up entirely of criminal hackers and refuses to attend (at the expense of great training and current knowledge).

Personal career story:

“I’ve worked in IT for 20 years now ever since I left college (in the UK that’s when you are 18). I’ve always had an interest in Security ever since I watched the movie Sneakers when I was a teenage. Four years ago I decided to dedicate some time to improve my skills in Security. I created a training plan (which I soon ignored), started stalking people on Twitter (security people), and started a blog to chronicle my journey. I’ve taken part in UK Cyber Security, written magazine articles about some of my coding projects, run workshops at conferences, written tutorials and tried to contribute to a community that at it’s heart wants you to succeed and is willing to share its time and experience with you. A year ago I moved into a security role at my current employer, I know do technical security as well helping define and build the companies Cyber Security Strategy. I also work for UK law enforcement helping fight Cyber Crime. I love security, it’s the biggest puzzle you can get in IT. It’s like a ever changing, challenging and exciting rollercoaster ride that makes me glad to go to work everyday.”

(Many thanks to Christina M)

What this job does:

As an entry level analyst you will most likely manage day-to-day processes around an existing I&AM/IDAM solution. As a senior analyst/architect you will design, build, test, deploy and implement I&AM architectures. This includes centralizing and automating firm-wide access control processes via an IDM tool which includes on-boarding/off-boarding, access requests & approvals, automation of flows, future integration of applications, maintenance of IAM technology infrastructure, app and user store integration. In this position you will interact with mostly every department in your org from senior management to associate.

Where are the jobs:

Professional services, government, financial services, technology companies, consulting and outsourcing industry.

What gives a candidate an edge:

Solid IT and technical background, system architecture, design and implementation, business ops and controls. Also, staying away from silos. Learning about other areas in information security/IT and the business. Also communication! If you understand how to translate business requirements into IT requirements and highlight value propositions from a risk/privacy perspective you will succeed.

Avoid this trap:

Believing that certifications like the CISSP/CISA alone will give you the experience and knowledge that you need to succeed. They will not. The best way to learn is hands on.

Personal career story:

“Trained in information technology and network administration. While attending university, I interned at the computer lab and landed a help desk/desktop tech shortly after. After graduation, I went on to work as a Jr. network admin where I honed my skills in server administration, server implementation, network upgrades, troubleshooting patch panels, implementing VOIP. I got an opportunity to work in IT security for a financial co in 2007. While I didn’t have formal infosec training at the time my previous experience and understanding of network implementations & keen interested, landed me the job. I then learned about Identity and Access management frameworks, risk governance, centralization of access management, RBAC, access certification & automation. Went on to implement a full fledged identity and access tool and process at a fin org in 2012. Never be afraid to ask questions, try something new and take chances.”


What this job does:

Endeavors to ensure that software, devices, or apps are developed with good security in mind from the bottom up. Identifies deficiencies as products are developed and tested and acts as a resource for the development team.

Where are the jobs:

Any reasonably sized organization that develops things, from software, to SCADA to operating systems, to devices which will connect to the IoT.

What gives a candidate an edge:

Excellent software or hardware development and engineering skills. A good understanding of how the product type being designed could be practically exploited. Certifications not only in developing the device or language, but securing it (for example, GWAPT, GSSP-.NET, or the CSSLP). This can vary widely by what is being engineered. Some devices or software might need to conform to government or industry security standards.

Avoid this trap:

Believing that you will always win the security argument with developers and management, even when your argument is reasoned and evidenced. Assuming that every project you will be asked to will be designed with security in mind from dayone (sometimes it will be tacked on later at the expense of overall security).

Personal career story:

“Way back in 2002, I decided to start building dynamic websites in PHP for hobbies of mine. (I was in middle school at the time.) Some of the folks in one of the communities I was trying to contribute to were very toxic, so I kept getting hacked. I quickly caught onto how they broke in and started learning how to stop more advanced attacks. I found myself on websites like HackThisSite and EnigmaGroup, but I always felt outclassed, so I just kept reading, learning, and writing better code. And that kept going on for years: Read, learn better habits and strategies, rewrite entire websites from the ground up, rinse and repeat. In 2013, I decided to start contributing to open source projects on Github. I quickly identified some flaws in the cryptography code used by CodeIgniter, Kohana, etc. that seemed really obvious to me (timing attacks on the HMAC verification that shielded the unserialize() in their session drivers from being a remote code execution vulnerability), but whose team members did not find so obvious. I had a similar experience with Facebook’s SDK developers (which I wrote about ). Recently I published Halite, a PHP library that serves as a user-friendly wrapper for libsodium to make high-speed cryptography accessible for PHP developers and I’m pushing to make libsodium a core PHP extension in 7.1.

Being a secure developer is challenging; you have to exist at the cross-section of keen information security awareness and still be able to keep up with people who write software full-time. But it’s also incredibly rewarding, as long as you learn this lesson earlier rather than later: People who specialize in secure development are incredibly rare. Things that seem obvious to you might not be.

The one thing I like most about my job is that I get to take rare knowledge (in my case, cryptography engineering) and apply it in areas where it would otherwise not touch (i.e. web applications)..”

Chapter 5: Red Team Careers



 What this job does:

 Pen-testers are the folks who simulate a real network attack on a target to identify their security flaws and vulnerabilities. They can look for these vulnerabilities across a wide range of platforms and architectures – from traditional networks’ DMZs, to SCADA systems, to complex internal networks. Their job is to play the bad guy within well documented rules of engagement, and report back to their employer what was discovered. Entry level and intern pen testing is a starting point for many people moving into ‘Red Team’ roles.

 Where are the jobs:

 Medium to large organizations, smaller organizations which handle highly sensitive data, contracting firms which provide these services.

 What gives a candidate an edge:

 Extensive knowledge of multiple operating systems’ operation, including command line, authentication, and permissions. Solid knowledge of networking. Knowledge of social engineering tactics. Comfort with common hacking tools like the Kali distro and its installed packages. Experience with Metasploit / Armitage / Cobalt Strike is useful. Good certifications to have include OSCP and GPEN, with specialized certifications and experience in specific systems as required.

 Avoid this trap:

 Thinking that penetration testing will be the rock star job the media makes it out to be. This isn’t an episode of Leverage. Except for when it is, occasionally. Penetration testing is a lot of work that involves legalities, meetings, and lots of paperwork. There are usually heavy restrictions on what pen testers can attack and when. The job can also be travel heavy for contractors.

 Personal career story:

“I have landed every single InfoSec-specific job I’ve ever gotten via making friends in non-Professional contexts. Game nights, house parties, book signings, poker games, bartending. . . when you allow your career to flow from organic, human interaction (as opposed to forced professional contexts), you have a much higher chance of ending up somewhere you actually WANT to be. You’ll click with your team (and possibly the company) better, you’ll be naturally motivated to work simply because you care, and this will likely lead to you hanging around a company longer, racking up that sweet, sweet vacation time. All of this stems from dropping the shop talk and the constant immersion in InfoSec, and saying ‘Hey; I’m just people, and you’re just people, and maybe us people can get something done somewhere by just being people together.“

Personal career story:

“I was going to school in Boston, knowing that I was going to go into computer security. My university required two coop terms for the degree, and I was lazy about the first one, so I did a term in a computer repair shop. For the second, I was determined to get a coop at a security firm. I searched around for all the local security shops, then cold called them asking if they had coop programs. There was some forensics shop, [redacted], and Core. The forensics shop had no coop. I interviewed with [redacted] and they turned me down.

So, when I went to Core, I compiled sanitized reports from freelance pen testing I’d done, presentations I’d given at a security meeting I organized on campus, and writeups of bugs for which I had CVEs. I laid them all out in front of the guy interviewing me, talked him through each one, and asked if he had any questions.
He smiled approvingly, nodded, and said I certainly seemed to know a lot about security.

He then asked me what I knew about marketing. It was at that moment I learned I was interviewing for a marketing position. I put my head in my hands and explained the misunderstanding. The gentleman across the table from me said that he’d be willing to give me the position, and that in any down time I had after doing marketing work, I could do security research. I accepted, and within a month, I’d scripted away all my marketing work, essentially resulting in being brought into a security research position. I impressed enough people that I ended up in a pen testing role, starting my career in infosec.”


 What this job does:
Similarly to a traditional, network-based penetration tester, a physical penetration tester tests an organization’s non-computer security measures. This can include evading guards, locks, or cameras to reach a target, breach a defense, or conduct a network penetration test from inside a building.

 Where are the jobs:

Due to the nature of the job, physical penetration testers almost exclusively work on a contract basis for other organizations.

 What gives a candidate an edge:

Knowing locks and security systems inside and out. Being great at social engineering people and playing a role even when circumstances change rapidly. Potentially the full network penetration testing skillset, as well.

 Avoid this trap:

Expect to travel. A lot. Engagements can be days or weeks long, and can even involve pretending to for days work at an organization you’re trying to exploit. Don’t expect the job to be constant fun and games. There’s lots of reconnaissance and research that goes into breaching a building’s security, and plenty of reports to write afterwards. Expect to potentially be arrested or even go to jail before your employer or contracting agency can clear things up legally.

 Personal career story:

“I made the move from “conventional” INFOSEC work to Physical Penetration when one client had a sysadmin rage quit.  We were called in to pop the domain controller and re-establish access for the company, but upon arrival learned the server room was locked (and the key had left with the ex-BOFH).  As they “awaited the locksmith” I offered to simply open the door for them.  They allowed it, we easily got in, used the pnordahl toolkit to give them back their admin accounts, etc.  But it was the door-opening that floored this client the most.

“Show us that again!” they entreated, and we spent another two (billable) hours just walking around their facility, explaining how their doors could be picked or bypassed. Knowledge that for me was merely a fun hobby turned out to be valuable to clients.  That’s the most key element of establishing yourself in some security sphere: figure out a weak surface that no one is protecting (because they don’t yet think to) and learn to be as well-versed as possible in that vein.

Then publicize your findings and share knowledge with others.  My associates and I would never have become known as go-to people for locks, alarm systems, elevator access controls, etc, had it not been for our talks at conferences and training at places like Black Hat and SANS, etc.

In that regard, I have to offer huge thanks to people like Heidi Potter, Bruce Potter, Beetle, Jeff Moss, Ed Skoudis, John Strand, BernieS, and many other conference organizers who encouraged their events to host lockpicking and other physical security content from me before I was as well-known.”


What this job does:

Vulnerability researchers study products and software in great detail to find hardware and software vulnerabilities so that they can be fixed in a timely manner.

Where are the jobs:

Medium to large software companies, hardware engineering companies, vulnerability research organizations. (Many vulnerability researchers are self-employed and work for bounties.)

What gives a candidate an edge:

Excellent computer science and/or electronic engineering skills (depending on the target products). Excellent reverse engineering skills. An intense desire to research and understand how things work.

Avoid this trap:

Assuming anything about gaining this career as a legitimate form of employment will be easy.

Personal career story:

“I started with computing at a young age. My uncle (a professor) gave me C and BASIC texts. I read them. Having only school computers, I mostly theorized and scribbled on paper. Years later my father purchased an IBM Aptiva (~1994), and established dial-up access into the RPI network. Shell and MUDs became my home amongst RPI students. The knowledge I would gain from those late night experiments would shape my future. A future in vulnerability research. Through keeping a Socratic approach to all things computer related, I established a variety of friendships and contacts within the InfoSec Industry. Having a passion for identifying, and proving out flaws in applications and devices drove me through the, sometime very annoying, monotony that can be research. I began consulting on-the-side while attending school for Biology, and was given some amazing opportunities with Albany Medical Center, NYS Prosecutors, and GE Global Research. Those opportunities lead to the expansion of fellowship I had within InfoSec, and exposed me to a wide variety of specificities within the industry. That exposure solidified my calling of research; and I haven’t looked back since.”



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