Attracting Customers with New Digital Experiences

Developing and Measuring a Modern Security Operations Organization

Hart Rossman’s job is to help customers build the confidence and technical capability to operate their most sensitive workloads with AWS in the cloud. His team spends their waking hours obsessing over how to continually raise the bar for the customer experience in addressing urgent needs around security, risk and compliance.

AWS enterprise strategist Clarke Rodgers spoke to Hart about how organizations can find and develop talent to help them achieve their security objectives, including modernizing and measuring security operations in a way that matters to customers.

Digital experiences that build customer confidence

Conversation in detail

Clarke (00:04):
Hart, thank you so much for joining us today.

Hart (00:06):
Thanks for having me Clarke. 

Clarke (00:08):
So, if you could spend a little time telling us about your background, how you came to AWS and what your current role is?

Hart (00:14):
Sure. So, before AWS, I was working in the defense contractor intelligence space, doing a lot of systems integration work, and I really liked it, I loved the mission, I loved supporting the U.S government and governments around the world and what they did and some regulated industries as well. But I had always kind of maintained this list in the back of my head of the top security companies, right. And in the early part of my career, those were largely consumer focused. So, antivirus, personal firewalls on your desktop, stuff like that. But over time, that list migrated into companies that were providing the infrastructure that makes the world go. And so, companies like Amazon, right, and other big infrastructure providers. And so, I was really at a point in my career, I was looking for that next move. And I wanted to go someplace where they were really innovating on security. That was going to make a difference, not just to a few customers who were very important, but really to the world. And so, I had this opportunity to come to AWS and took it.

Clarke (01:12):
And what is your current role at AWS today?

Hart (01:14):
So, these days, I'm the director of the security and infrastructure global specialty practice and professional services, which is a bit of a mouthful. But what it really means is that my job is to help customers build the confidence and technical capability to operate their most sensitive workloads with us in the cloud.

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My job is to help customers build the confidence and technical capability to operate their most sensitive workloads with us in the cloud.


Clarke (01:33):
Thank you for that Hart. … we sort of switch gears to the customer perspective. Our customers CISOs, they're always looking for hiring security talent, and it can be very difficult to find those types of people. When you have a shortage of security talent, what kind of advice would you give to a CISO or other hiring manager at a customer organization, as far as looking for that right person, even if they may not have the deep security skills that you're looking for?

Hart (02:02):
Yeah, I think a lot of it comes down to that corporate culture. And we often find ourselves in sort of two different conversations. The first is bringing in deeply technical engineering resources and then developing a program to get them comfortable with whatever the new technology is, Lambda, Containers, whatever it might be, KS. Or the security aspect of it. So, bringing in that deeply technical engineering resource and helping them understand how to build securely, how to think securely, how for example, to begin every sprint by starting with a threat model to generate your user stories that you're then going to sprint against, instead of just the functional requirements from the product manager.  So, those sorts of skills. And then the other end of the spectrum of course, is there's a lot of really talented security people in other parts of the security community. So, they might be in audit, they might be in compliance, they might be in other areas and it's an opportunity to bring them into a different part of the security community and allow them, if they're interested to become more technical, to develop those engineering skills, to develop this product development, product management skills. And that's really helpful as well. The one thing I often offer, and again, it goes back to something we look for on our team is, the creative types tend to be the most successful. The lateral thinkers, the artists, the poets. They tend to be really good at making that adjustment over time. And not to stereotype anybody, but that kind of flexibility and agility and mindset often allows them to kind of come along quite quickly.

Clarke (03:38): 
Customers, they seem to really be turning towards the security engineering, build security into applications and infrastructure that they're managing. As you know there's another aspect of security and that sort of operational security and just making sure everything is operating as it should and let me see a red flag here and let me react to that, that sort of thing. What's that right balance between the sort of engineering mindset and the operational mindset?

Hart (04:04):
Yeah, that's a super important question. I actually spent quite a bit of time talking to senior executives about that because when they're early in their journey, not just with the cloud, but I think with application modernization, which many of them are doing, regardless of their involvement with AWS. The emphasis is often on the dev part of dev ops. And so, they're thinking about really, how do they build and deploy their workloads better? They haven't necessarily thought all the way through the operate part. And then when you add in security operations, there's a very particular nuance there that really needs to be addressed. One of the things that I've found is helpful is when we start talking about operations, we can't really talk about programs and initiatives anymore. A lot of times during a migration, a lot of times during a new workload build, it's really very programmatic. You have a product manager, you have a migration lead, but when we're talking about security operations, you have to have that 24 by 7, 365, reliability, security and sense and response, activity which comes with a conventional ops center mentality. Now, we don't need to be constrained by the four walls of an actual operation center. Because, we have systems in the cloud that will help us do the same thing. But we need to sort of shift that executive mindset. And it's often as simple as saying, well, what metrics matter to you in operations? We've talked about the migration, we've talked about the development. We know what's important to you and what success looks like, but what does security operations look like to you from a metrics standpoint? And once we have that conversation, we can often very easily orient into what that looks like and now start to truly bring dev and ops together in a meaningful way from a security and safety standpoint.

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We're talking about setting security expectations for the organization that are going to drive year over year transformation, not just hitting a particular number this year.

Clarke (05:50):
So, I'll ask the million dollar question, what are some key metrics that customers are typically looking for, from an operational perspective?

Hart (05:57):
Yeah. It depends again on their goals and their objectives. One of the things we will look at are things like dwell time. One of the really cool things about having immutable infrastructure, is that you can have very low rehydration rates for your entire data center in the cloud. Instead of taking months or sometimes years to rebuild and rehome an application, many of our customers have it down to hours and some minutes for smaller workloads. And so, if you can rebuild your entire data center in an hour, now you can start to think about, how do we change the conversation about dwell time for an adversary? How do we change the conversation around vulnerability management and the long tail of patching? And we can start to really look at those metrics that help us drive agility, scalability, reliability, which ultimately to security.

Clarke (06:55):
So, a lot of our conversation today has been around engineering security operations, sort of traditional nuts and bolts of running a security organization. In a lot of the conversations I have with CISOs, they're really concerned about how do I report security in the appropriate business context and how do I frame cyber risk in business terms that my board or my senior directors will understand? Do you have any offerings around this, in this place with sort of security as a business leader, as opposed to just sort of security operations in the traditional metrics that we think about?

Hart (07:31):
Yeah, we do. And it's actually another great example of working backwards from the customer. Early on, in the days of building the security part of the security risk and compliance practice, we started to get those kinds of questions from customers. And I had experience and many of the people at the time of my team had experience in security consulting, but none of us had the personal responsibility that a CISO had in protecting the organization. And so, after getting that request a few times, we thought we've got to go find some CISOs to come work with us. And so, that's just what we did. We built an executive security advisory practice where we have chief information security officers, heads of risk and audit. Who've gone on the cloud journey themselves with AWS and they're now on our team. And they can do that peer level advisory work, backed up by the strong engineering and operational folks to actually help implement that executive strategy. And it's been really, really good. We're able to have conversations around metrics. I don't mean metrics like the operational metrics we're talking about earlier. We're talking about key performance indicators. We're talking about setting security expectations for the organization that are going to drive year over year transformation, not just hitting a particular number this year. 

Clarke (08:53):
Got it. So, with the customer CISOs that you work with, are you seeing any trends in their sort of business level reporting to their boards? When I speak to customer CISOs, yes, you still need to have all the metrics of the machines we patched and the viruses we stopped and the attacks we stopped and things like that. But what's the advice you give to articulate that in business terms to people who may not have the deep security expertise yet may hold the purse strings to your budget and other operations?

Hart (09:29):
Yeah. I think there's a few different points of view. One is the transformation angle that I mentioned earlier. If you set the right goal and expectation, there's this tremendous pull through effect. And an example I'll use is, as the CISO set the goal of being able to rehydrate your entire data center in the cloud, in a few days, let's say, every 48, 72 hours. Working backwards from that, it has this massive knock on effect to how you do BCPDR. How you do, build, deploy, and operate, how you do tests. It forces everybody to automate, it forces everybody to accelerate, which ultimately reduces time to value for every one of those under the hood infrastructure activities. So, lower cost, faster to market, greater response time for your customers. So, it really drives some great outcomes across the business by having one right security expectation that by the way is probably a yearly transformation. So, it might be, we want to get down to rehydration every 45 days this year and then we want to get down to 15 days next year and then we want to be down to 48 hours the following year. So, year over year, you're going to use that one security objective to drive all these other business outcomes.

Clarke (10:52):
And then track that with the board as you're reporting.

Hart (10:54):
Exactly.

Clarke (10:55):
That's awesome. Hart, thank you so much for joining us today.

Hart (10:57):
Cool. Thank you for having me.

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About the Leaders

Hart Rossman, AWS Director Global Security & Infrastructure Practice

Hart Rossman
AWS Director Global Security & Infrastructure Practice

Hart Rossman is the Director of Security for AWS Global Services. In this role he is responsible for building with customers, building with AWS Service teams, partner enablement, growth strategies, engagement security, and engagement operations. As a customer or partner you might have experienced some of our innovative work on your behalf including the AWS Cloud Adoption Framework Security Perspective, AWS Security Reference Architecture, Jam Service & events, Security Epics, or the Control Tower Account Factory for Terraform.

Clarke Rodgers
AWS Enterprise Strategist

As an AWS Enterprise Security Strategist, Clarke is passionate about helping executives explore how the cloud can transform security and working with them to find the right enterprise solutions. Clarke joined AWS in 2016, but his experience with the advantages of AWS security started well before he became part of the team. In his role as CISO for a multinational life reinsurance provider, he oversaw a strategic division’s all-in migration to AWS.

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