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The Security Industry
How To Survive Becoming Management
WHAT HAPPENS
TO HACKERS THAT GO PRO
?
A Little Back Story
The Personal Case Study Of Dil
An Accidental Hacker Manager
My name is Christien Rioux.
Opinions are my own, not my company’s
but they are probably right, regardless.
HI!
Understanding my recommendations requires
understanding my history a bit, pardon my ego briefly.
WHO IS THIS GUY?
GROWING UP
Born in West Virginia, Raised In Maine
Nothing to do but system programming
Circa 1983, learned my first programming language:
Applesoft Floating Point BASIC on the Apple ][+,
followed by 6502 assembler
Spent 4 years in high school writing a CRPG
Lost it in a hard drive crash
Learned valuable lesson about backing up
Father brought home display models of computers from store
SCHOOL
MIT: BS in CS
Picked terrible handle, laughed out of #hack on IRC
Wrote possibly the first public stack overflow advisory for Windows
Wrote a search engine at MIT for my senior project
Graduated in 1998
Worked for a financial startup
Found I loved security and left after 11 months
without giving up my fingerprints to the man
GET A JOB, KID
L0pht Heavy Industries
First to go full time at end of 1998
L0phtCrack, AntiSniff, Numerous advisories
Tao Of Windows Buffer Overflow, Back Orifice 2000
@stake
Along with 20 other people, founded @stake in 2000
Acquired in 2004 by Symantec
Spun out Veracode in 2005
MAKE IT REAL
Veracode
Acquired funding and launched Veracode in 2006
Started as Chief Scientist
Now also Chief Innovation Officer
Initial author of the Veracode Static Binary Analyzer
Architect for Veracode Mobile, iOS platform lead
The Effects Of Time
How Dil Lost His Hair
T+0 YEARS
Job Title: Programmer
Publications: None
Motivation: Get a job,
figure out what’s going on
Hair: Brown, Sassy, Side-Part
T+5 YEARS
Job Title: Hacker
Publications: Advisories,
password auditing tools, etc.
Motivation: Get in the
media as much as possible.
Hair: Unix Sysadmin
T+10 YEARS
Job Title: Security Researcher
Publications: Binary analysis
software
Motivation: Do something
impossible
Hair: Receding Muppet Blue
T+15 YEARS
Job Title: Chief Scientist
Publications: Mobile software
analyzer, speaking, the
occasional 0-day
Motivation: Improve the state
of the industry
Hair: Migrating to ears/nose
YOUR FATE IS NOT SEALED
These changes are not just due to time,
many are consequences of decisions we have chosen to make.
I’ve made certain choices,
you will likely make completely different ones.
Only through introspection can we answer the question:
How do we build a better hacker manager?
Management was never my intention, but a consequence of valuing the
implementation of my own ideas. It had to happen.
The Growth Of The
Security Industry
How Time Is Shaping Us
TIMELINE
Physical Security (Since the beginning of recorded history)
Gestation Period for the Internet And Computers (1960-1980)
Computer Security Gets Real: The Morris Worm (1988)
Network Security (1990-2000)
The @stake Effect (2000-2004)
Security Architecture (2005-2010)
(Big) Data Security and Application Security (2010-Today)
OPERATIONAL MODELS
Consultancy / Boutique
Pure manual services
Tech-assisted manual services
Pen Testing, Architecture review
Product Sales
Developer/SDLC
Enterprise Targeted
End-User Targeted
Infrastructure
Enterprise
Security Department
Security on IT Team
Security QA for Engineering
Software As A Service
Recurring revenue model
Full automation
Outsourced Security
How Do We Define
Success?
Business v.s. Personal
BUSINESS SUCCESS FACTORS
Shareholder Value
Market Leadership
What these have in common is: accurate and frequent measurement
“You can’t improve what you can’t measure”
Stability And Predictability
HEIGHTOFLINE
DISTANCE FROM LEFT
EXIT STRATEGY
Run Out Of Money
Angry VCs
Sad founders
Fire sale of everything
Start applying for dumb job
Build Quick
Little to no investment
Sell early
Time is right, get lucky
Tight timeframe
Long Haul
Long term multiple round investment
Weathering the storm
Get mature
Go public or get bought
“Lifestyle Company”
Long term multiple round investment
Slow drain on personal money
Remain private, die old
Go public, die old
Survive and transfer company
through nepotism.
PERSONAL SUCCESS FACTORS
PERSONAL GOALS
What motivates you? Why are you doing this?
Altruism? Money? Fame? Boredom? Ego?
Do you like your job?
Where do you want to be in 5, 10, 15 years?
And once you do get some money, how are you going to
not act like one of those ‘people with money’?
Getting famous sounds like a good idea
but once you’re famous, it’s quite hard to turn that into money.
WHAT IS GOOD ENOUGH?
Success is different for everyone, but we tend to agree
that money != happiness. As money can be an enabler for
future success, it is a reasonable goal.
I tend to think that happiness is a requirement to build
wealth, as the fortitude required to grow your career
requires that you LOVE what you are doing.
What is good enough?
Is there a perfect job/role/project?
SCHOOL?
Gotta get a job eventually.
If you don’t want to do security for a living, feel free to skip this
section. My guess is if you’re here, you care.
If you hack all the time you will get bad grades.
This is not all bad, but may have unintended consequences.
Graduate.
Chances are you are not Steve Jobs or Bill Gates.
Nothing looks worse than someone
who can’t finish what they started.
The Effect Of Hacker
Culture On Companies
Side-Effects, Intentional And Not
SKEPTICISM
Healthy
“Prove to me that you’ve done some work securing that machine
before we put it out on the Internet.”
Unhealthy
“Everyone has faults. It is only a matter of time before I discover
yours, and exploit it, leaving you a powerless pariah to your
occupation.”
PARANOIA
Healthy
“We should conduct full security reviews of the software with each
quarterly release, and automated reviews with every minor
release.”
Unhealthy
“I think the Sales and Marketing team have it out for the
Engineering team.”
MAKER ETHICS
Independence
One good engineer or security expert or consultant can make all
the difference working on his/her own.
Idea generation / IP Factory
New product ideas come from good brainstorming and careful
attention to detail.
ENCOURAGING HACKER CULTURE
Google Time
20% of employees time is spent on non-work projects, many of
which end up benefiting Google.
Hackathons
~3 day ‘hacking runs’ where all work projects are stopped and
people work on non-work ideas, some work related, some not
work related and share them with the company.
Security Awareness Training
People with the awareness shouldn’t be afraid to speak up. We
tend to be condescending toward the teeming clueless masses. We
should at least show them how to evolve.
ROLE PROGRESSION
Individual Contributor
Project Lead
Middle Management
Executive Management
Founders, CEOs, and Board Members “oh my”
Beware The Peter Principle
The Ten Commandments
Of Hacker Management
Management Survival Tips
RULE #1
Thou shalt appear presentable,
approachable, and kind.
Appearance, it matters. Your first impression matters.
A good manager avoids the troll-under-the-bridge
image that we tend to embrace as hacker ‘outsiders’.
RULE #2
Thou shalt be a good team leader
and a good individual contributor.
Make the team better than the sum of their parts,
else why are you there at all?
RULE #3
Thou shalt prioritize the team you are on,
rather than the team you lead.
When forced to prioritize, you should focus on supporting
the team(s) you are on. Being a leader comes second to
being a good contributor, since you should not be afraid to
delegate to the best of your direct reports.
RULE #4
Thou shalt in be inclusive of many skillsets
and expertise in your organization.
It takes all kinds of people.
Surrounding yourself with really smart people
all the time guarantees that the
‘boring work’ will never get done.
RULE #5
Thou shalt embrace time and
project management techniques.
We love to take on impossible projects that take an infinite
amount of time, don’t we? Do not bite off more than you
can chew. You are not invincible. Keeping your team all
together with tools will keep your schedules realistic.
RULE #6
Thou shalt not depend on
‘rock stars’ and ‘hero coders’.
We love to take on impossible projects that take an infinite
amount of time, don’t we? Do not bite off more than you
can chew. You are not invincible. Keeping your team all
together with tools will keep your schedules realistic.
RULE #7
Thou shalt embrace process.
Learn Agile, Scrum and all that other shit.
Get with Kanban, learn some tools to help you with it.
Get religion around process.
The best departments have a ‘single point of entry’ for
communications with people outside the department.
Think ‘abstraction barrier’ not ‘silo’.
RULE #8
Thou shalt not require perfection,
for it is the mortal enemy
of ‘good enough’.
Raising the bar is what our industry is all about. If you think
you’re going to ‘win’ or ‘catch the bad guy’ you’re not
thinking this through. Same goes for your projects, and your
interactions with your team.
Recognize ‘good enough’ when you see it.
RULE #9
Thou Shalt Trust But Verify
Give people a chance to do the right thing.
Security people tend to turn into micro-managers.
That doesn’t mean that work should be accepted
without review, but let people do their job, dammit!
RULE #10
Thou shalt give feedback well,
and take feedback even better.
Management isn’t easy, because personalities
and interpersonal relationships are hard.
It’s about giving and receiving feedback. Hackers don’t necessarily
like criticism from people that don’t know their stuff.
So, know your stuff, know how to give feedback
and be a good hacker manager.
THANK YOU
FOR YOUR TIME, ENJOY BSIDES!

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The Security Industry: How to Survive Becoming Management BSIDESLV 2013 Keynote

  • 1. The Security Industry How To Survive Becoming Management
  • 2. WHAT HAPPENS TO HACKERS THAT GO PRO ?
  • 3. A Little Back Story The Personal Case Study Of Dil An Accidental Hacker Manager
  • 4. My name is Christien Rioux. Opinions are my own, not my company’s but they are probably right, regardless. HI! Understanding my recommendations requires understanding my history a bit, pardon my ego briefly. WHO IS THIS GUY?
  • 5. GROWING UP Born in West Virginia, Raised In Maine Nothing to do but system programming Circa 1983, learned my first programming language: Applesoft Floating Point BASIC on the Apple ][+, followed by 6502 assembler Spent 4 years in high school writing a CRPG Lost it in a hard drive crash Learned valuable lesson about backing up Father brought home display models of computers from store
  • 6. SCHOOL MIT: BS in CS Picked terrible handle, laughed out of #hack on IRC Wrote possibly the first public stack overflow advisory for Windows Wrote a search engine at MIT for my senior project Graduated in 1998 Worked for a financial startup Found I loved security and left after 11 months without giving up my fingerprints to the man
  • 7. GET A JOB, KID L0pht Heavy Industries First to go full time at end of 1998 L0phtCrack, AntiSniff, Numerous advisories Tao Of Windows Buffer Overflow, Back Orifice 2000 @stake Along with 20 other people, founded @stake in 2000 Acquired in 2004 by Symantec Spun out Veracode in 2005
  • 8. MAKE IT REAL Veracode Acquired funding and launched Veracode in 2006 Started as Chief Scientist Now also Chief Innovation Officer Initial author of the Veracode Static Binary Analyzer Architect for Veracode Mobile, iOS platform lead
  • 9. The Effects Of Time How Dil Lost His Hair
  • 10. T+0 YEARS Job Title: Programmer Publications: None Motivation: Get a job, figure out what’s going on Hair: Brown, Sassy, Side-Part
  • 11. T+5 YEARS Job Title: Hacker Publications: Advisories, password auditing tools, etc. Motivation: Get in the media as much as possible. Hair: Unix Sysadmin
  • 12. T+10 YEARS Job Title: Security Researcher Publications: Binary analysis software Motivation: Do something impossible Hair: Receding Muppet Blue
  • 13. T+15 YEARS Job Title: Chief Scientist Publications: Mobile software analyzer, speaking, the occasional 0-day Motivation: Improve the state of the industry Hair: Migrating to ears/nose
  • 14. YOUR FATE IS NOT SEALED These changes are not just due to time, many are consequences of decisions we have chosen to make. I’ve made certain choices, you will likely make completely different ones. Only through introspection can we answer the question: How do we build a better hacker manager? Management was never my intention, but a consequence of valuing the implementation of my own ideas. It had to happen.
  • 15. The Growth Of The Security Industry How Time Is Shaping Us
  • 16. TIMELINE Physical Security (Since the beginning of recorded history) Gestation Period for the Internet And Computers (1960-1980) Computer Security Gets Real: The Morris Worm (1988) Network Security (1990-2000) The @stake Effect (2000-2004) Security Architecture (2005-2010) (Big) Data Security and Application Security (2010-Today)
  • 17. OPERATIONAL MODELS Consultancy / Boutique Pure manual services Tech-assisted manual services Pen Testing, Architecture review Product Sales Developer/SDLC Enterprise Targeted End-User Targeted Infrastructure Enterprise Security Department Security on IT Team Security QA for Engineering Software As A Service Recurring revenue model Full automation Outsourced Security
  • 18. How Do We Define Success? Business v.s. Personal
  • 19. BUSINESS SUCCESS FACTORS Shareholder Value Market Leadership What these have in common is: accurate and frequent measurement “You can’t improve what you can’t measure” Stability And Predictability
  • 21. EXIT STRATEGY Run Out Of Money Angry VCs Sad founders Fire sale of everything Start applying for dumb job Build Quick Little to no investment Sell early Time is right, get lucky Tight timeframe Long Haul Long term multiple round investment Weathering the storm Get mature Go public or get bought “Lifestyle Company” Long term multiple round investment Slow drain on personal money Remain private, die old Go public, die old Survive and transfer company through nepotism.
  • 23. PERSONAL GOALS What motivates you? Why are you doing this? Altruism? Money? Fame? Boredom? Ego? Do you like your job? Where do you want to be in 5, 10, 15 years? And once you do get some money, how are you going to not act like one of those ‘people with money’? Getting famous sounds like a good idea but once you’re famous, it’s quite hard to turn that into money.
  • 24. WHAT IS GOOD ENOUGH? Success is different for everyone, but we tend to agree that money != happiness. As money can be an enabler for future success, it is a reasonable goal. I tend to think that happiness is a requirement to build wealth, as the fortitude required to grow your career requires that you LOVE what you are doing. What is good enough? Is there a perfect job/role/project?
  • 25. SCHOOL? Gotta get a job eventually. If you don’t want to do security for a living, feel free to skip this section. My guess is if you’re here, you care. If you hack all the time you will get bad grades. This is not all bad, but may have unintended consequences. Graduate. Chances are you are not Steve Jobs or Bill Gates. Nothing looks worse than someone who can’t finish what they started.
  • 26. The Effect Of Hacker Culture On Companies Side-Effects, Intentional And Not
  • 27. SKEPTICISM Healthy “Prove to me that you’ve done some work securing that machine before we put it out on the Internet.” Unhealthy “Everyone has faults. It is only a matter of time before I discover yours, and exploit it, leaving you a powerless pariah to your occupation.”
  • 28. PARANOIA Healthy “We should conduct full security reviews of the software with each quarterly release, and automated reviews with every minor release.” Unhealthy “I think the Sales and Marketing team have it out for the Engineering team.”
  • 29. MAKER ETHICS Independence One good engineer or security expert or consultant can make all the difference working on his/her own. Idea generation / IP Factory New product ideas come from good brainstorming and careful attention to detail.
  • 30. ENCOURAGING HACKER CULTURE Google Time 20% of employees time is spent on non-work projects, many of which end up benefiting Google. Hackathons ~3 day ‘hacking runs’ where all work projects are stopped and people work on non-work ideas, some work related, some not work related and share them with the company. Security Awareness Training People with the awareness shouldn’t be afraid to speak up. We tend to be condescending toward the teeming clueless masses. We should at least show them how to evolve.
  • 31. ROLE PROGRESSION Individual Contributor Project Lead Middle Management Executive Management Founders, CEOs, and Board Members “oh my” Beware The Peter Principle
  • 32. The Ten Commandments Of Hacker Management Management Survival Tips
  • 33. RULE #1 Thou shalt appear presentable, approachable, and kind. Appearance, it matters. Your first impression matters. A good manager avoids the troll-under-the-bridge image that we tend to embrace as hacker ‘outsiders’.
  • 34. RULE #2 Thou shalt be a good team leader and a good individual contributor. Make the team better than the sum of their parts, else why are you there at all?
  • 35. RULE #3 Thou shalt prioritize the team you are on, rather than the team you lead. When forced to prioritize, you should focus on supporting the team(s) you are on. Being a leader comes second to being a good contributor, since you should not be afraid to delegate to the best of your direct reports.
  • 36. RULE #4 Thou shalt in be inclusive of many skillsets and expertise in your organization. It takes all kinds of people. Surrounding yourself with really smart people all the time guarantees that the ‘boring work’ will never get done.
  • 37. RULE #5 Thou shalt embrace time and project management techniques. We love to take on impossible projects that take an infinite amount of time, don’t we? Do not bite off more than you can chew. You are not invincible. Keeping your team all together with tools will keep your schedules realistic.
  • 38. RULE #6 Thou shalt not depend on ‘rock stars’ and ‘hero coders’. We love to take on impossible projects that take an infinite amount of time, don’t we? Do not bite off more than you can chew. You are not invincible. Keeping your team all together with tools will keep your schedules realistic.
  • 39. RULE #7 Thou shalt embrace process. Learn Agile, Scrum and all that other shit. Get with Kanban, learn some tools to help you with it. Get religion around process. The best departments have a ‘single point of entry’ for communications with people outside the department. Think ‘abstraction barrier’ not ‘silo’.
  • 40. RULE #8 Thou shalt not require perfection, for it is the mortal enemy of ‘good enough’. Raising the bar is what our industry is all about. If you think you’re going to ‘win’ or ‘catch the bad guy’ you’re not thinking this through. Same goes for your projects, and your interactions with your team. Recognize ‘good enough’ when you see it.
  • 41. RULE #9 Thou Shalt Trust But Verify Give people a chance to do the right thing. Security people tend to turn into micro-managers. That doesn’t mean that work should be accepted without review, but let people do their job, dammit!
  • 42. RULE #10 Thou shalt give feedback well, and take feedback even better. Management isn’t easy, because personalities and interpersonal relationships are hard. It’s about giving and receiving feedback. Hackers don’t necessarily like criticism from people that don’t know their stuff. So, know your stuff, know how to give feedback and be a good hacker manager.
  • 43. THANK YOU FOR YOUR TIME, ENJOY BSIDES!