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How to Sell InfoSec to the C-Suite
A Playbook to Build Your Case and Get Your Budget
Infosec
How to Sell InfoSec to the C-Suite
2
My BIG
Security Plan
You need the whole team behind
you to keep your business running.
But sometimes IT managers can feel pretty alone in the backfield.
Take network security. Your business can’t afford the kind of attack
that hit Target and Home Depot. You’ve set up the best defense you
can, but now you need more money, tools, and support.
That’s what this hands-on playbook is for.
We’ll walk you through the steps to analyze
your situation, put together a business case,
and present it successfully to the C-suite. And
because you don’t always win your first contest,
we’ll also give you a back-up plan.
Let’s get started.
Playbook Checklist
4  Talk to department managers.What network resources do theyneed to meet their goals?
4  What’s the impact if business unitslost network resources?
4  What are hard costs (actual
costs or revenue losses) if criticalsystems were hacked?
4  Estimate soft costs (hits to
reputation, brand, and customersatisfaction) as well.
4  Take this opportunity to evangelizeyour security plans and get yourpeers on board.
3
How to Sell InfoSec to the C-Suite
Step 1. Scouting Report
Before you step out of the locker
room, you need to know what
you’re up against. A business
impact analysis helps you
understand what’s important to
keep the business running, so you
know what’s at risk.
4
How to Sell InfoSec to the C-Suite
Step 2. Training Day
You’ve established the risk if the business lost access to critical systems
due to a security incident. Now it’s time for a security audit to look for
vulnerabilities. You can do this yourself, or bring in experts to help.
Playbook Checklist
4  Explore outside agencies and online tools to perform a security audit.
4  Create an InfoSec policy: everything from how often passwords should
be changed to how employees remotely access company resources.
4  Get consensus on the policy from other departments so they can
proactively help secure assets.
4  Review and update policies annually, including InfoSec, NDAs, AUPs, etc.
4  Keep the business running. Get approval before addressing any issues.
4  Plan how you’re going to turn audit results into understandable, actionable information.
How to Sell InfoSec to the C-Suite
5
How to find audit resources:
4 Talk to your outside auditor about reviewing
your cybersecurity readiness.
4 Get referrals from the security community
and current technology partners.
4 Ask on technical mailing lists and social
networking sites such as LinkedIn.
4 Search online for “vulnerability assessment
services,” “security assessment services,”
“penetration testing services,” “incident
detection and response services,” or “threat
exposure management.”
Required Team Reading
Stay up-to-date on risks and solutions.
Subscribe to security forums and
reports and review them regularly.
InformationWeek’s DarkReading
http://www.darkreading.com
Internet Storm Center
https://isc.sans.edu
KrebsonSecurity
krebsonsecurity.com
Naked Security
https://nakedsecurity.sophos.com
Reading Room
http://www.sans.org/reading-room
Schneier on Security
https://www.schneier.com
WatchGuard Security Center
http://watchguardsecuritycenter.com
How to Sell InfoSec to the C-Suite
6
Step 3. Go the Distance
This is when you put your security program through its paces
using security scans. Even the best security programs have
issues, so if you don’t find anything, there’s a good chance
something’s wrong with your methodology.
Playbook Checklist
4  Do your research. Read and talk to experts so you
know what kind of scanning tools you need.
4  Before running any scan, get approval first.
4  Make sure you understand the tools and what effect
they might have on the business.
4  Analyze network size and scan intensity to estimate
time required (a few hours to weeks).
4  Run the scans, scheduling network maintenance
time if necessary.
How to Sell InfoSec to the C-Suite
7
Sample Workouts
High-quality, open source security scanning tools are widely
available online at no cost. Start with a general-purpose
tool and move to specialty scans as needed.
General Tools
NMAP is a network mapper and fingerprinting software
http://nmap.org
OpenVAS is a vulnerability scanner
http://www.openvas.org
Specialty Tools
Zed Attack Proxy (ZAP) is a tool for finding vulnerabilities in web applications
https://www.owasp.org/index.php/OWASP_Zed_Attack_Proxy_Project
Sqlmap is a penetration testing tool that automates the process
of detecting and exploiting SQL injection flaws
http://sqlmap.org
Playbook Checklist
4  Review your audit and scan
reports. Prioritize issues basedon importance of the asset andlikelihood of the attack vector beingexploited.
4  Use your business impact analysisto prioritize risks appropriately. Ahigh-level vulnerability in a test sitemight be less important than amoderate risk in a critical system.
4  Identify which items require littleeffort or resources to mitigate.
4  Develop a remediation plan alongwith the stakeholders from thebusiness impact analysis.
How to Sell InfoSec to the C-Suite
8
Step 4. Flag On the Play
Now that you’ve discovered
where the issues are, it’s time for
remediation. Decisions on what to
remediate (or not) should be based
on the severity of the vulnerability, the
chance of it being exploited, and the
exposure it would cause.
How to Sell InfoSec to the C-Suite
9
Step 5. Get Your Game Face On
It’s time to put your training to the test. Presenting to the C-suite may feel
like the big league, but this is your playing field. If senior management
doesn’t understand the risks, it’s your job to educate them.
Playbook Checklist
4  Own the security concerns you’re reporting.
4  Present risks in terms that management understands
and that are specific to the business.
4  Don’t use misleading statistics as scare tactics.
4  Be transparent about what you’ve already done.
4  Explain how you’ve exhausted current resources and what you need to succeed.
4  Identify stakeholders and sponsors from meetings with business unit managers.
4  Be iterative in your communication until you get the support you need.
What we have
doesn’t work.
We need
to fix it— NOW.
I have
a plan!
How to Sell InfoSec to the C-Suite
10
Tips for success
4  Don’t send out raw reports.
Apply context to help managers
understand your decisions.
4  Frame the conversation with
security requirements related to
your industry (SOC for publicly
traded companies, HIPAA for
healthcare, PCI DSS for retailers,
etc.).
4  Consider creating custom
reports for each business unit.
Document the process	 Explain each riskAudit/scan methodology	 Whether risk is acceptableWhen they were performed	 How to mitigate itParticipation of stakeholders 	 What happens if you don’tRemediation steps	
Estimated cost and effort
Reporting  Statistics
Regularly update and distribute reports that include
a concise, business-focused executive summary.
How to Sell InfoSec to the C-Suite
11
Step 6. The Season Isn’t
Over Until It’s Over
Security is important, but your C-suite has
to balance competing business initiatives,
challenges, and expenses. You may not
get everything you ask for right away, but
you’re always just one security incident
away from getting funding. Be prepared.
Playbook Checklist
4  Keep your reports current so you’re
ready when you’re called up.
4  Run free tools and remediate every
issue you can.
4  Add remediation actions to your
regularly distributed reports.
4  Be prepared to show progress since
your last presentation.
4  If you can’t fix an issue, provide
options: accept the risk, assign
resources, or take at-risk assets offline.
How to Sell InfoSec to the C-Suite
12
PRODUCTS
Step 7. Don’t Bring Anything
Less than Your “A” Game
Once you’re ready to implement new security services, make sure
your team is well-equipped for the challenge. WatchGuard can help
with a full suite of security products and top performance to meet
the needs of businesses of all sizes.
How to Sell InfoSec to the C-Suite
13
About Watchguard
WatchGuard® Technologies, Inc. is a global leader of integrated, multi-function business security solutions that
intelligently combine industry standard hardware, best-of-breed security features, and policy-based management
tools. WatchGuard provides easy-to-use, but enterprise-powerful protection to hundreds of thousands of businesses
worldwide. WatchGuard products are backed by WatchGuard LiveSecurity® Service, an innovative support program.
WatchGuard is headquartered in Seattle, Wash. with offices throughout North America, Europe, Asia Pacific, and Latin
America. To learn more, visit WatchGuard.com.
No express or implied warranties are provided for herein. All specifications are subject to change and any expected
future products, features, or functionality will be provided on an if and when available basis. ©2015 WatchGuard
Technologies, Inc. All rights reserved. WatchGuard, the WatchGuard logo, Fireware, and LiveSecurity are registered
trademarks of WatchGuard Technologies, Inc. All other trademarks and tradenames are the property of their
respective owners.
505 Fifth Avenue South
Suite 500
Seattle, WA 98104
www.watchguard.com
North America Sales
+1.800.734.9905
International Sales
+1.206.613.0895

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Selling Infosec to the CSuite

  • 1. How to Sell InfoSec to the C-Suite A Playbook to Build Your Case and Get Your Budget Infosec
  • 2. How to Sell InfoSec to the C-Suite 2 My BIG Security Plan You need the whole team behind you to keep your business running. But sometimes IT managers can feel pretty alone in the backfield. Take network security. Your business can’t afford the kind of attack that hit Target and Home Depot. You’ve set up the best defense you can, but now you need more money, tools, and support. That’s what this hands-on playbook is for. We’ll walk you through the steps to analyze your situation, put together a business case, and present it successfully to the C-suite. And because you don’t always win your first contest, we’ll also give you a back-up plan. Let’s get started.
  • 3. Playbook Checklist 4 Talk to department managers.What network resources do theyneed to meet their goals? 4 What’s the impact if business unitslost network resources? 4 What are hard costs (actual costs or revenue losses) if criticalsystems were hacked? 4 Estimate soft costs (hits to reputation, brand, and customersatisfaction) as well. 4 Take this opportunity to evangelizeyour security plans and get yourpeers on board. 3 How to Sell InfoSec to the C-Suite Step 1. Scouting Report Before you step out of the locker room, you need to know what you’re up against. A business impact analysis helps you understand what’s important to keep the business running, so you know what’s at risk.
  • 4. 4 How to Sell InfoSec to the C-Suite Step 2. Training Day You’ve established the risk if the business lost access to critical systems due to a security incident. Now it’s time for a security audit to look for vulnerabilities. You can do this yourself, or bring in experts to help. Playbook Checklist 4 Explore outside agencies and online tools to perform a security audit. 4 Create an InfoSec policy: everything from how often passwords should be changed to how employees remotely access company resources. 4 Get consensus on the policy from other departments so they can proactively help secure assets. 4 Review and update policies annually, including InfoSec, NDAs, AUPs, etc. 4 Keep the business running. Get approval before addressing any issues. 4 Plan how you’re going to turn audit results into understandable, actionable information.
  • 5. How to Sell InfoSec to the C-Suite 5 How to find audit resources: 4 Talk to your outside auditor about reviewing your cybersecurity readiness. 4 Get referrals from the security community and current technology partners. 4 Ask on technical mailing lists and social networking sites such as LinkedIn. 4 Search online for “vulnerability assessment services,” “security assessment services,” “penetration testing services,” “incident detection and response services,” or “threat exposure management.” Required Team Reading Stay up-to-date on risks and solutions. Subscribe to security forums and reports and review them regularly. InformationWeek’s DarkReading http://www.darkreading.com Internet Storm Center https://isc.sans.edu KrebsonSecurity krebsonsecurity.com Naked Security https://nakedsecurity.sophos.com Reading Room http://www.sans.org/reading-room Schneier on Security https://www.schneier.com WatchGuard Security Center http://watchguardsecuritycenter.com
  • 6. How to Sell InfoSec to the C-Suite 6 Step 3. Go the Distance This is when you put your security program through its paces using security scans. Even the best security programs have issues, so if you don’t find anything, there’s a good chance something’s wrong with your methodology. Playbook Checklist 4 Do your research. Read and talk to experts so you know what kind of scanning tools you need. 4 Before running any scan, get approval first. 4 Make sure you understand the tools and what effect they might have on the business. 4 Analyze network size and scan intensity to estimate time required (a few hours to weeks). 4 Run the scans, scheduling network maintenance time if necessary.
  • 7. How to Sell InfoSec to the C-Suite 7 Sample Workouts High-quality, open source security scanning tools are widely available online at no cost. Start with a general-purpose tool and move to specialty scans as needed. General Tools NMAP is a network mapper and fingerprinting software http://nmap.org OpenVAS is a vulnerability scanner http://www.openvas.org Specialty Tools Zed Attack Proxy (ZAP) is a tool for finding vulnerabilities in web applications https://www.owasp.org/index.php/OWASP_Zed_Attack_Proxy_Project Sqlmap is a penetration testing tool that automates the process of detecting and exploiting SQL injection flaws http://sqlmap.org
  • 8. Playbook Checklist 4 Review your audit and scan reports. Prioritize issues basedon importance of the asset andlikelihood of the attack vector beingexploited. 4 Use your business impact analysisto prioritize risks appropriately. Ahigh-level vulnerability in a test sitemight be less important than amoderate risk in a critical system. 4 Identify which items require littleeffort or resources to mitigate. 4 Develop a remediation plan alongwith the stakeholders from thebusiness impact analysis. How to Sell InfoSec to the C-Suite 8 Step 4. Flag On the Play Now that you’ve discovered where the issues are, it’s time for remediation. Decisions on what to remediate (or not) should be based on the severity of the vulnerability, the chance of it being exploited, and the exposure it would cause.
  • 9. How to Sell InfoSec to the C-Suite 9 Step 5. Get Your Game Face On It’s time to put your training to the test. Presenting to the C-suite may feel like the big league, but this is your playing field. If senior management doesn’t understand the risks, it’s your job to educate them. Playbook Checklist 4 Own the security concerns you’re reporting. 4 Present risks in terms that management understands and that are specific to the business. 4 Don’t use misleading statistics as scare tactics. 4 Be transparent about what you’ve already done. 4 Explain how you’ve exhausted current resources and what you need to succeed. 4 Identify stakeholders and sponsors from meetings with business unit managers. 4 Be iterative in your communication until you get the support you need. What we have doesn’t work. We need to fix it— NOW. I have a plan!
  • 10. How to Sell InfoSec to the C-Suite 10 Tips for success 4 Don’t send out raw reports. Apply context to help managers understand your decisions. 4 Frame the conversation with security requirements related to your industry (SOC for publicly traded companies, HIPAA for healthcare, PCI DSS for retailers, etc.). 4 Consider creating custom reports for each business unit. Document the process Explain each riskAudit/scan methodology Whether risk is acceptableWhen they were performed How to mitigate itParticipation of stakeholders What happens if you don’tRemediation steps Estimated cost and effort Reporting Statistics Regularly update and distribute reports that include a concise, business-focused executive summary.
  • 11. How to Sell InfoSec to the C-Suite 11 Step 6. The Season Isn’t Over Until It’s Over Security is important, but your C-suite has to balance competing business initiatives, challenges, and expenses. You may not get everything you ask for right away, but you’re always just one security incident away from getting funding. Be prepared. Playbook Checklist 4 Keep your reports current so you’re ready when you’re called up. 4 Run free tools and remediate every issue you can. 4 Add remediation actions to your regularly distributed reports. 4 Be prepared to show progress since your last presentation. 4 If you can’t fix an issue, provide options: accept the risk, assign resources, or take at-risk assets offline.
  • 12. How to Sell InfoSec to the C-Suite 12 PRODUCTS Step 7. Don’t Bring Anything Less than Your “A” Game Once you’re ready to implement new security services, make sure your team is well-equipped for the challenge. WatchGuard can help with a full suite of security products and top performance to meet the needs of businesses of all sizes.
  • 13. How to Sell InfoSec to the C-Suite 13 About Watchguard WatchGuard® Technologies, Inc. is a global leader of integrated, multi-function business security solutions that intelligently combine industry standard hardware, best-of-breed security features, and policy-based management tools. WatchGuard provides easy-to-use, but enterprise-powerful protection to hundreds of thousands of businesses worldwide. WatchGuard products are backed by WatchGuard LiveSecurity® Service, an innovative support program. WatchGuard is headquartered in Seattle, Wash. with offices throughout North America, Europe, Asia Pacific, and Latin America. To learn more, visit WatchGuard.com. No express or implied warranties are provided for herein. All specifications are subject to change and any expected future products, features, or functionality will be provided on an if and when available basis. ©2015 WatchGuard Technologies, Inc. All rights reserved. WatchGuard, the WatchGuard logo, Fireware, and LiveSecurity are registered trademarks of WatchGuard Technologies, Inc. All other trademarks and tradenames are the property of their respective owners. 505 Fifth Avenue South Suite 500 Seattle, WA 98104 www.watchguard.com North America Sales +1.800.734.9905 International Sales +1.206.613.0895