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Am I a lost cause?... (need some pro help here).

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gliTch

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Post Tue Jan 27, 2009 4:40 am

Am I a lost cause?... (need some pro help here).

Hello all, I'm new here, and it looks like they have a lot of the same thing I'm about to ask here, BUT.... I feel as though my story is a little different:

Ok, so in '02 I got my A.S. for Computer Network Technology. Fresh out I looked for work, but couldn't get hired because of the "NO EXPERIENCE" clause. So I joined the military, got into the intel community, got a clearance (which I prefer not to talk about here). and got a honorable discharge. Now: I'm a civilian again and i still dream of a job in the INFOSEC field. But i haven't really done anything with my degree. It went to waste while in the military it seems. I still to this day consider myself to be far above the level of knowledge of an everyday IT. I've been looking to get in to pentesting for quite some time now. Past that A.S. that I earner almost 7 years ago i really haven't done anything to show continued education. So here comes the major questions:

I have  a family now, debt, (you know all that adult stuff). So there's no way I can afford to go back to college now to say earn my Master in Comp. Sci. ...I'm really not all that interested in having a IT/Helpdesk/"...Help! i forgot the password to my email" kind of job. Instead I want to hack. Plain and simple. Been that way for years. Now I just want to make it my career. I can run just about any OS, Win (all) 'Nix, (used UNIX in the military) and use BT3 as a personal favorite. Although I've never loaded and ran Free BSD (...maybe my next personal project). Point is, I'm NOT just some beginner. I've been in it for a while without ever really being IN the field. So, If I was looking to break into the pentesting/INFOSEC world, how would you recommend i do it? Where would I start? These things that may come common to some are not to me because I've never made it to that field. What Certs should I look at getting? What books might you recommend that could held catch me up? And honestly, does it even seem possible to still break into the field (no pun intended) with only a vast knowledge/extreme will/and only a few certs?

Any feedback would be appreciated.

Thanx in adv.

-gliTch
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venom77

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Post Tue Jan 27, 2009 11:51 am

Re: Am I a lost cause?... (need some pro help here).

From my experience, the only way you're going to get something without prior experience to show and only saying "hey, well I've been doing this at home as a hobby for X years," is to start networking with people. Share what you're interested in, what you've been doing, etc. and you might find someone willing to bring you on board.

Aside from that, I think your best bet would be to get a certification or two. That still doesn't guarantee that you're going to walk into any position (and probably not a pentesting job right off the bat either). If you have the non-professional experience and the knowledge like you're saying, it'd probably get a good idea to certify that. You say you know all versions of Windows, so why not go get an MCSA/MCSE/MCITP certification? Better yet, shoot for an SSCP or CISSP (if eligible). I think those alone will bump you up past the helpdesk position. By no means do they make you a pentester, but at least you'd be pointing in a good direction.

The toughest obstacle will be getting directly into that role you want without other experience first. Hell, if I had an answer for you, I'd be doing it myself :) Unfortunately, the reality is that you have to start somewhere and work your way up.

Welcome to the community.

BillV
Last edited by venom77 on Tue Jan 27, 2009 11:54 am, edited 1 time in total.
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Bogwitch

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Post Tue Jan 27, 2009 2:35 pm

Re: Am I a lost cause?... (need some pro help here).

Your clearance should stand you in good stead. Approach one of the security testing firms that get defence or government contracts, explain your interest and maybe accept a lower starting wage in return for training.

In the meantime, practice! Get a lab set up, get some pentesting framework documents to see what steps you'll need to take for pentesting and play - it sounds as though you'll enjoy it anyway and it will be cheaper than drinking beer all day long.

Failing that, take the helpdesk job at a company that trains their staff and become the security evangelist.
CISSP, C|EH, C|HFI
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sgt_mjc

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Post Tue Jan 27, 2009 5:08 pm

Re: Am I a lost cause?... (need some pro help here).

glitch,

Thanks for your service. I recently separated from the AF as well where I waas aircrew. I know am working in information assurance. things I learned along the way include meeting people. I now work with one of the guys that retired from my last unit, CCAF. Along the way, he was a mentor and helped steer me towards security. It also helped get the interview. What really sealed the deal though, is that I was able to show that I really wanted into the field. To do this, I went and got my CEH certification with my own money. I didn't do it through the AF since it wasn't taught at an accredited institution. This showed my employer that I was motivted to learn and expand things outside my comfort zone. My suggestion is get to know people here. Get a few certs. If you have the GI Bill, it will pay for most exams. And always be willing to learn. Oh, and a clearance helps whether it is just a secret or a ts.

If you need any help, just ask.
Mike
Mike Conway
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gliTch

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Post Wed Jan 28, 2009 3:06 am

Re: Am I a lost cause?... (need some pro help here).

Wow, well.... Thanks for the quick and positive responses everyone. I'm going to try to do this the best I can, so stick with me:  :-)

"Aside from that, I think your best bet would be to get a certification or two."

I've decided to get as many certs as I can. Right now I work offshore, (plenty of time to study while on boats) and I'm making enough money now to afford it. So My plan of action now is to get at least all the certs mentioned on EH (that are in the Ethical Hacking side). I'll study all year long, save money... Then when my 2 weeks of vacation start I spend the 1st week cramming and the 2nd week taking as many certs as I can. Being realistic, out of the 7 they mention on this site if i can land 3-4 of those I'd feel much better about going into '10 with that.

oh, and:

"You say you know all versions of Windows, so why not go get an MCSA/MCSE/MCITP certification?"

Because sadly i HATE Microsoft. Can't stand to be in a windows environment. Now, not to say I can't. The point I was trying to make is that I know my way around WINDOWS-X and that I can if i have to type of thing. ....And at this point I'll save someone reading some time from typing. YES I know that just about anywhere I go in IT i'll be working with windows :-(  I'm just a MAC/Linux guy. If it was up to me i'd wipe MS off the face of the planet myself if i could. ...But you get the point: I don't like it, that's all. Nothing more/nothing less.

Ok, who's next?

"Your clearance should stand you in good stead. Approach one of the security testing firms that get defence or government contracts, explain your interest and maybe accept a lower starting wage in return for training."

While this is truly a great concept it just wont work right now having a family to worry about. Also I'm about to have to file bankruptcy real soon, (got laid off last year). Which is going to (i think) put a real big dent in my clearance or I'll lose it completely. .... But still not a bad idea. I've already applied at all the major defense contractors: Lockheed,Northern G, Boeing, etc. And the F.B.I. ... still no word back. I figure, they're slow or I suck lol. ....But only time well tell in those cases... you never know.

"In the meantime, practice! Get a lab set up, get some pentesting framework documents to see what steps you'll need to take for pentesting and play"

Absolutely! Normally I use neighbors and friends and test their security and explain what I did/how I did it. And then walk them through tightening up their security. But I think that is a great point is to take my PC that my wife using and start figuring out a few new things. ... It's like it's such a simple idea that I can't believe I never thought of it before. Thanx.


Next up:

"Thanks for your service. I recently separated from the AF as well where I waas aircrew."

You're VERY welcome, and thank you as well for all your hard times and struggles you been through for this country.

"What really sealed the deal though, is that I was able to show that I really wanted into the field. To do this, I went and got my CEH certification with my own money."

Well as I mentioned earlier I plan on getting as many certs as I can with my own money and on my own. Hopefully if I can find a good enough company, I'll keep studying and maybe they can pay for the bigger ticket items like my MSCE and such.

"If you have the GI Bill, it will pay for most exams. And always be willing to learn. Oh, and a clearance helps whether it is just a secret or a ts."

Well, I'll use my GI Bill for as much as I can, (I didn't spend 5 years in, and get an honorable DD214 for it to go to waste). And of course I'm always willing to learn. It's like a light switch was flipped when I got out, and my brain got turned on. The problem is that I don't always know "what" to learn. I just made a nice book list on amazon (about 8-9 books) that all deal with CEH/other certs, Hacking/Pentesting, setting up network security and such. I plan on getting those when I get home from this job. As far as my clearance goes it's a secret, but now I'll have to see if my bankruptcy is going to affect it (and I'm sure it will) but time will tell.

Also I've snooping around this site and found some very useful ideas. I'm going to start working on a site (like an e-Resume) and update it as I get my certs and my goals for future knowledge and education I'll be seeking.

But really to all of you that posted, thank you. Normally I don't like doing the quoting  thing but in this case I didn't want anyone who had something helpful to say go unnoticed. Thank you all for your time and understanding to the situation. If there's ever anything I can help with, just name it.  ;-)


-gliTch
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geekyone

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Post Wed Jan 28, 2009 3:35 am

Re: Am I a lost cause?... (need some pro help here).

I've got one possible suggestion for you.  With your clearance and experience it would be fairly easy to pick up a overseas military contracting job.  That market has cooled off a little but there is still a lot of work out there.  It's a little tough for someone with a family but if your hard up for money it's a good option.  If you can put up with being away from your family for six months or a year you can make a lot of money and possibly even get IT experience at the same time.  Iraq and Afghanistan are the obvious choices but even working for oil companies in Africa is really good money.  I don't know if this is something you would be interested in but I thought I would throw out the suggestion.  Welcome to EH-Net and Good Luck!
CISSP, CEH, GPEN, GCIH, GCFA
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gliTch

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Post Wed Jan 28, 2009 3:46 am

Re: Am I a lost cause?... (need some pro help here).

Well I must say that now after having 2 kids the likelihood that I'll ever go to a hot zone is slim to none (if I can help it). As far as the time thing. I've been through 3 six month deployments, and my wife's been through 2 of those. And now I'm at a job that's had me out here (on the boat) since Jan. 14th. and I'm begging stay out until Mar.-Apr. (I'm only going in to do taxes, otherwise I'd stay out here longer.) But that's another reason I'm fighting to into a land job (been on the water for almost 7 years now) I don't mind leaving my family to get done what I have to get done, but I'm getting to the point where I don't want to miss my kids growing up. The overseas thing I don't mind one bit, I'd go in the drop of a hat if the conditions were right, and one of those conditions are NO hot zones lol. But thanks for the idea. ;-)

-gliTch
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sgt_mjc

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Post Wed Jan 28, 2009 9:17 am

Re: Am I a lost cause?... (need some pro help here).

What part of teh country are you looking at? I know most people assume CA for the IT world, but I was plesantly surprised to end up in Huntsville, AL. Around here its a who's who of defense contractors.
Mike Conway
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blackazarro

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Post Wed Jan 28, 2009 11:32 am

Re: Am I a lost cause?... (need some pro help here).

Today I stumbled upon a site that perhaps may be of interest to you with regards to entering the world of Pentesting.

So you want to break into the world of penetration testing... The following is a suggestive route I've laid out from a technical perspective. Its purpose is to introduce you to a broad technical level of "know how". Some, even many will disagree with the methodology and structure that I've written, but my intention here is to get you to a point where you can understood how it all comes together from the top down and vice versa.

I've received a lot of e-mails regarding a post I made on the "pentesters" mailing list so I decided to write a sort of no bs framework which should give anyone reading this and putting it into practice, enough information to be a versatile security professional and enough know how, in order to break into most of the security sectors, network security, penetration testing, firewall engineering, etc.

This is perhaps the one biggest challenge I faced - trying to summarize years worth of work into a compacted framework. Attempting to dissect and explain it all, without boring the reader. This is a two year framework, if you were looking for the easy way out, there is none, period. Security especially when it comes to pentesting is an ever evolving dynamic arena. You seriously need to understand a great deal about a lot of topics, protocols, etc., With all that said, enough rambling.


For the rest of the info please refer to the following link:

http://www.infiltrated.net/pentesting101.html

This is a framework created by Jesus Oquendo.
Security+, OSCP, CEH
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gliTch

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Post Thu Jan 29, 2009 5:50 am

Re: Am I a lost cause?... (need some pro help here).

I'm willing to go anywhere that's willing to take me, and anywhere that I can consider a learning experience, (which at this point would be anywhere lol.)

-gliTch
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silxp

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Post Thu Jan 29, 2009 7:09 am

Re: Am I a lost cause?... (need some pro help here).

gliTch wrote:I've been looking to get in to pentesting for quite some time now. Past that A.S. that I earner almost 7 years ago i really haven't done anything to show continued education.

-gliTch


Pentesting... What a wonderful misinterpreted field. As someone who was performed quite a few pentesting jobs beginning 1998, the field of pentesting is very fast, often confusing (to a degree) and can be fun yet a PITA (pain in the...)

For starters I wrote the "Pentesting 101" document which is linked here. It was meant as a "primer" of what I perceive a good pentester should learn. Your best bet is to do the following - seriously: Create a flowchart of the OSI layer and associate learning to each layer. You could start it either way you want from the application layer down - or the physical layer up.

After this is done, associate tasks with those layers, for example, on the application layer you may be versed in say, perl programming or ASP. Take the time to go through each layer and think about what you'd need to learn to master security on that layer. Find out information on security books associated with those topics and read, read, read.

You can do so in a 50k view approach working granularly on your way down. Now, if you read the primer, I started to give a barebones approach to operating systems, technologies (networking, etc.,) one seriously needs to understand. Learn as much as you can about interoperability between the layers, program interactions, etc.

It's a difficult concept to piece together because you just can't say "well I want to be a pentester" when there are so many variables. For example, you might know Linux, BSD, Solaris, networking like the back of your hand, but what good would it do if need to know RACF?

There is so much to constantly learn, but there is always a common core to it all. Personally, I prefer RFC style reading working my way up to a program or protocol. If I understand what's at the core of it (rfc's can be extremely high level) - then my theory is, the rest falls into place no matter the operating system. SMTP is SMTP is SMTP - Exchange and Postfix are two different delivery mediums, but the core will always be the same. Trust but VRFY ;)

Before shooting for say the SSCP or CISSP - be advised, those will NOT help you in your pentesting career. They'll help you get your foot in the door to an interview - but they will show you zero on the pentesting side. It's an art (pentesting) - that you have to be very fluent in. This includes creativity and knowledge of the core. So personally, I'd go through the document I wrote - while a little broad - it should give you a baseline of things to expect.

Sincerely,


J. Oquendo
sil@{infiltrated.net,disgraced.org,tormenting.net}
OSCP, C|EH, CNDA, CHFI, SGFA, SGFE
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gliTch

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Post Thu Jan 29, 2009 4:44 pm

Re: Am I a lost cause?... (need some pro help here).

Hello J.,
Thanx for writing and noticing me. I would 1st off like to once again thank the community all of you have here. This is my 1st post and I've got some VERY insightful replies. Instead of some forums where people would just like to point out your weaknesses, all of you actually seem interested in helping. ... and for that I thank you from the bottom of my digital heart. ;-)

Ok, so today's case/point:

I would like to start off by saying thanks to all, but especially to blackazarro for 1st putting up the 101. The 1st thing I did when I saw that was fill up literally everyday of my iCal until 01Feb10 ...I took that writing VERY seriously because 7-10 years ago you couldn't find a good "step-by-step" starting point. ...Look we all know that NO ONE can just tell you, "Poof, Your're a hacker!...Now go forth and h@x0r the Planet!" ... But out of ALL of my years looking for something, this is it! This is the 101 that I needed to kick me in the back of the head to get started! ...These are all things that I'm familiar with but am an expert in none by no sense. So I took the time to actually come to a very clean decision based on the help i received here. I'm going to take this year and follow that 101 to a "T". Now I know that's not everything I need to know, and yes I do understand that it's ever changing, (that's half the fun if you ask me. How boring would pentesting be if it was like say like my job? I survey in the gulf of mexico... The same thing day in and day out. I always like a never challenge). So I'm going to be a pentester, but you're right, there's so much involved with it, and I know that I'll never be great at everything, but the one thing I do know is that my super-power happens to be my "gift of gab" (thanx don) I can talk my way into / out of ANY situation. So for me, my main focus of pentesting was networking and S.E. but now I see that it's kind of an "all-or-none" path, and if that's if, then so be it. ... J. would you mind if I kept your email and write you when I hit the wall and can't figure out something? Oh and btw, I also made a list of all the Cisco books and I plan on going through them as well. (thanx J.) I guess what I'm saying here is, don't expect some kid asking stupid $h!7 like "d00d, can you teach me how to h@x0r my friends email?" ...I've seen it a million times on forums and honestly I just think that's ignorant! I an willing to learn. I am willing to teach myself (as much as I can). I am willing to be self motivated. All I need is the person who understands that to point me in the write direction. ((Any other volunteers at this time are also welcome.))  ;-) Ok enough rambling for now. My case: I have my work cut out for me for the next 24 months (this year/study. next year/certs.) My point: Thank you everyone.

Feel free to email me anytime (if there is anything that I can do for any of you)
or if you just feel like there's something useful that someone can learn, if you think of me then please send it my way as well. IT WILL GET READ, and I will try to understand it to the best of my ability. ....Thanx all.

gli7cha@gmail.com

-gliTch     
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silxp

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Post Fri Jan 30, 2009 9:16 am

Re: Am I a lost cause?... (need some pro help here).

Here's my updated suggestion on books, again, they're suggestive - everyone differs.

Build Your Own Security Lab - Michael Gregg
978-0-470-17986-4

You can find "e-variations" of similar books written by others, but this book has a consolidation of building and explaining some of the attack vectors to look for, etc.

Exploiting Software How to Break Code - Hogland
0-201-78695-8

This book gives excellent guidance with not only understanding some of the workings of software but the structure of interconnectivity between clients and servers. Again, you may not want to be a programmer but understanding what is occurring is vital.

Then you can go through Reversing for Newbies which has some ok themes/reads:
http://www.tuts4you.com/download.php?list.17

Penetration Tester's Open Source Toolkit
1-59749-021-0

Personally, I'm not a fan of the book since there was little for me to glean from it however, it offers a lot for those "semi" experienced in networking and the concepts of penetration testing. My issue with this book, was the use of too many tools. I particularly don't like to rely on tools. Something I learned from a friend at Kore Logic.

Re-iterating it all: This could go on for days and a book list can grow so much. It's what you put into it. Now you will want to read both OSSTMM and ISSAF and understand them fully as well as some of the emerging OWASP tools and concepts. So again, there is a lot to think about, there is a lot to plan, but the serious key to it all, is have fun doing it. The moment I get bored, I'm out of this industry period.

So last note... Don't focus on the certs too much - learning and understanding it on your own accord will allow you to have the capacity to pass the cert when the time is right. If you focus on passing X cert, you can introduce "self induced failure" where you're focusing on one specific thing, so caught up on that one thing, letting other skills/strengths lag - know what I mean... Understanding it, learning it makes it all come together eventually - wherein at any point in time you'd be able to understand the focus on any cert question.

For example, I took a PSP (Physical Security Professional) assessment exam out of boredom, I've never truly dealt with physical security (chain link fences, etc.) - minor tasks for technological things - however, out of the 100 questions I got 3 wrong. The concepts were the same for me, mentally I replaced terms like "garage" with "dmz", "floor" with VLAN and so on. When you understand the core - from my perspective - all other stuff falls into place
OSCP, C|EH, CNDA, CHFI, SGFA, SGFE
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charlottebandit

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Post Sat Jan 31, 2009 5:17 am

Re: Am I a lost cause?... (need some pro help here).

There is a lot of liability for pentesting positions which is why it usually requires tons of experience not only on the pentesting side, but also excellent knowledge in several of these areas:  systems, networks, databases, web apps/services, secure programming, security hardware, and forensics.  So in order to get the experience with the above criteria, you have to start somewhere, so I recommend with going with what you know & have experience with:  Linux/Unix!

By doing such, you'll get tons of experience with the above while also learning a valued "trade" that many partners seek.  There are also top-tier linux security certifications like the RHCSS which a Redhat Linux security cert.  It's gonna take lots of time & practice to get there as you'll have to first obtain your RHCE which covers Redhat systems.  This and your clearance will do wonders for you.  NOt only that, you'll learn and get experience with many projects that will give you perspective when doing pentests.  Through there you could implement, enforce, and assess security policies in businesses. 

Some get into security through networks (I did), while other get there through secure programming.  The thing is, you REALLY need either a BS/MS to get your foot in the door or a high-level cert (RHCE/RHCSS, CCIE, CEPT/LPA) if you don't have much direct experience.  The above certs require a hands-on component which  requires the testee to REALLY know the products rather than cheat their way through it using braindumps, so they're highly respected across the board. 

Business want to know exactly what you bring to the table.  Now that you have responsibilities, it's harder to allocate time to getting ramped up, but not impossible.  Federal contractors tend to require a BS degree at a minimum, along with multiple certs and internships for a jr position for candidates without a lot of "direct" experience.  Without a BS or high-level certs, you'll most likely land help-desk jobs which suck.  A high-level cert will begin opening doors because they require tons of hands-on experience, but no guarantee either as you'll more often than not be given a performance interview to show your stuff. 
MS, CCSP, CCNP, CCDP, CEH, CHFI, CPTS
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charlottebandit

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Post Sat Jan 31, 2009 5:47 am

Re: Am I a lost cause?... (need some pro help here).

Silxp gave a great response.  You said that you have 24 months to learn?  Wow!  You should be able to knock out the RHCE, RHCSS, CCSP, and either CEPT or LPT for a position into the security realm.  Once there, then go forth and conquer!

As for the possible bankruptcy, that will kill your clearance even though they "say" it's a case-by-case deal.  Had that problem 5 years ago and couldn't even get a secret clearance for a position in a hotzone! 

Just as silxp mentioned, there's so much to learn and consider because this is an ever changing field that requires solid understanding of multiple vendor products, architectures, varied solutions, and tons more which requires time.


**Easiest way to get into pentesting?  Pick up a hardware vendor cert that has several security solutions (like CCSP) but REALLY know how to implement them and not just PASS a test, work for a partner that implements those solutions in a small state or one with less population, and begin offering FREE network & security assessments to qualify security sales.  This option will most likely be a drop in salary for the first year or two, but will give you an opportunity to gain some experience along with how security controls work.  I've seen a couple of people do this not even realizing it!  LOL  And they had no prior experience, nor degree.  From there they jumped to another partner for a better position doing the same, but for better pay obviously.  Soon they'll have enough knowledge and experience to do pentesting full-time along with a deep understanding of security architectures too. 

Outside of government work, it's ALL about sales.  Especially engineers. 
Last edited by charlottebandit on Sat Jan 31, 2009 5:53 am, edited 1 time in total.
MS, CCSP, CCNP, CCDP, CEH, CHFI, CPTS

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