Building A Modern Security Engineering Team Zane

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1 Building A Modern Security Engineering Team Zane Lackey April 2016

2 WHO IS THIS GUY ANYWAY? 1. Built and led the Etsy Security Team Spoiler alert: what this presentation is about 2. Co-founder / CSO at Signal Sciences

3 This talk is about lessons learned being at the forefront of the shift to agile/continuous deployment/devops

4 FOR SECURITY TEAMS, THE WORLD HAS CHANGED IN FUNDAMENTAL WAYS: 1. Code deployment is now near-instantaneous

5 FOR SECURITY TEAMS, THE WORLD HAS CHANGED IN FUNDAMENTAL WAYS: 1. Code deployment is now near-instantaneous 2. Merging of development and operations means more people with production access

6 FOR SECURITY TEAMS, THE WORLD HAS CHANGED IN FUNDAMENTAL WAYS: 1. Code deployment is now near-instantaneous 2. Merging of development and operations means more people with production access 3. Cost of attack has significantly dropped

7 Near-instantaneous deployment?

8 A simulation of deploying code in the waterfall model

9 An example: Etsy pushes to production 50 times a day on average

10 Constant iteration in production via feature flags, ramp ups, A/B testing

11 WAIT A MINUTE! But doesn t the rapid rate of change mean things are less secure?!

12 Actually, the opposite is true!

13 Compared to: We ll rush that security fix. It will go out in about 6 weeks. - Former vendor at Etsy

14 What makes continuous deployment safe?

15 What makes continuous deployment safe? Visibility.

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19 The same hard lessons are slowly shifting to security

20 Ex: Which of these is a quicker way to spot an attack?

21 A

22 B

23 Surface security info for everyone, not just the security team

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26 *Mullets sold separately Building a rad culture

27 In the shift to continuous deployment, speed increases by removing organizational blockers

28 Trying to make security a blocker means you get routed around

29 Instead, the focus becomes on incentivizing teams to reach out to security

30 KEYS TO INCENTIVIZING CONVERSATION: ü Don t be a jerk. This should be obvious, but empathy needs to be explicitly set as a core part of your teams culture.

31 KEYS TO INCENTIVIZING CONVERSATION: ü Don t be a jerk. This should be obvious, but empathy needs to be explicitly set as a core part of your teams culture. ü Make realistic tradeoffs. Don t fall in to the trap of thinking every issue is critical. Ex: Letting low risk issues ship with a reasonable remediation window buys you credibility for when things actually do need to be addressed immediately.

32 KEYS TO INCENTIVIZING CONVERSATION: ü Don t be a jerk. This should be obvious, but empathy needs to be explicitly set as a core part of your teams culture. ü Make realistic tradeoffs. Don t fall in to the trap of thinking every issue is critical. Ex: Letting low risk issues ship with a reasonable remediation window buys you credibility for when things actually do need to be addressed immediately. ü Coherently explain impact. This would allow all our user data to be compromised if the attacker did X & Y paints a clear picture, where The input validation in this function is weak does not.

33 KEYS TO INCENTIVIZING CONVERSATION: ü Reward communication with security team. T-Shirts, gift cards, and high fives all work (shockingly) well.

34 KEYS TO INCENTIVIZING CONVERSATION: ü Reward communication with security team. T-Shirts, gift cards, and high fives all work (shockingly) well. ü Take the false positive hit yourself. Don t send unverified issues to dev and ops teams. When issues come in, have the secteam verify and make first attempt at patch.

35 KEYS TO INCENTIVIZING CONVERSATION: ü Reward communication with security team. T-Shirts, gift cards, and high fives all work (shockingly) well. ü Take the false positive hit yourself. Don t send unverified issues to dev and ops teams. When issues come in, have the secteam verify and make first attempt at patch. ü Scale via team leads. Build relationships with technical leads from other teams so they make security part of their teams culture.

36 TL;DR (THE SECTION FORMERLY KNOWN AS CONCLUSIONS )

37 TL;DR Ø Adapt security team culture to DevOps and continuous deployment by: Surfacing security monitoring and metrics Incentivize discussions with the security team When creating policy, don t take away capabilities Ø Drive up attacker cost through bug bounty programs, countering phishing, and running realistic attack simulations

38 THANK YOU! Signal Sciences Zane