Reimagining Cyber

Aligning cybersecurity with startup business goals

July 12, 2022 Reimagining Cyber Season 1 Episode 37
Reimagining Cyber
Aligning cybersecurity with startup business goals
Show Notes Transcript

Ty Sbano, CISO for Vercel, shares his unique perspective on running the security business in the start-up space, from how to approach the interview process, how to gain trust early, and how to remain focused on the right priorities. 

Rob and Stan ask Ty:
- how he engages and makes  plan and prioritises
- the approaches he's  taken
- setting expectations
- metrics he works to
- how much time  is spent is on the organisational side versus what you're providing, as a service or product?
- instilling a positive culture
- how can we evolve what we've been doing for four decades on cybersecurity to address today and tomorrow's new threats.

Rob Aragoa  00:18
Welcome to the Reimagining Cyber podcast where we share short and to the point perspectives on the cyber landscape. It's all about engaging yet casual conversations and what organisations are doing to reimagine their cyber programmes while ensuring their business objectives are top priority. With my co host, Stan Wisseman, Head of Security Strategists, I'm Rob Aragao Chief Security Strategist.  So Stan, who do we have joining us for this episode?

Stan Wisseman  00:45
Rob, our guest today is Ty Sbano. He is currently the CISO for Vercel. He has had the opportunity to be in security leadership roles for very large firms as well as for startups. His primary career focus has been developing application and product security programmes for companies like Capital One, Target, Lending Club, and JP Morgan Chase. Ty, it's great to have you with us today, really looking forward to this episode and this opportunity to speak to you. Anything else you'd like to add about your background?

Ty Sbano  01:18
No, I think that's pretty good. I'm starting year number 18 in information security, if I don't consider like my undergrad time when I was working full time, which this would be year 20, to be honest with you, but in the grand scheme of you know, security, IT tech work,  it's crazy to think how long I've been doing this. And I really always appreciate a chance to pause, stop, think and  reflect and having these types of chats allow me to  look back and, and really analyse my career track of how I've gotten here. And thank you for asking me to join today.

Stan Wisseman  01:51
No, it's great. You know, whenever anyone takes a leadership role,  they should take time to assess and understand the current state of the organisation and then make a plan and execute on it. When you come into cybersecurity, leadership roles, and you've had the opportunity to do that many organisations, how do you establish your priorities? And,  I know that sometimes you've you've been brought in to help clean up somebody else's mess. But that's not always the case. But how do you typically engage and make your plan and prioritise?

Ty Sbano  02:30
Yeah, I think it really starts even prior to actually getting there, right? It's the interview process, you start to gain a lot of intelligence and intellect. And I think the idea of the interview process, everyone's putting their best foot forward. But I think the right companies, the right culture, pull no punches. They really tell you the story, they tell you the challenges, they say where the opportunities are, if it's all glowing, and great, you know, it's not going to be real. Once you get there, there's going to be a lot of the odds and ends of like, 'this isn't what we talked about'. And I can tell you like, within security, because of your expertise, because your time and role and your subject matter like focused work. Once you get there, you're going to reveal things that folks that don't have that level of depth and knowledge, you're just going to uncover and you have to adjust accordingly. Right. So I think you have to start during the interview process to really ascertain 'what am I actually going to do'. And I think the best CISOs out there, start building their plan before they even get there for their first day, which is something I highly recommend. And I know it's counterintuitive but if you want to be successful, you got to come prepared. And I think within security, it's you know, if you don't have a plan, and you're making it up on the fly,  it's probably not going to be that good. So I think from that point, when you have your first day or your first week looking at the agenda of like, how do you get on boarded? What are the controls? Why were you even brought there? And I think my career in the past, five, six years has been very different than the first, you know, 10-12 years, which was very hyper focused on application product security for larger organisations. For startups you have to be a lot more agile. And I'll definitely focus the conversation and narrative there. So I think once you get to the shop in a startup, where do you start? Because anywhere is going to be okay. But in reality, your first act matters so much to building or destroying the confidence of what you're going to do there and the organisation and if you're on the tail end of you know, not so great experience or maybe they hired the wrong folks for the role or you got to help move someone out of the company or you got a disruptive big old project that's not been working well.  I've been there, and I love to just work on tough problems, because I think that really drives creativity that drives a lot more of your own internal resiliency of working through adversity and honestly 18 years deep, I am at a point where there's no emotional reaction to a lot of this anymore regardless of the incident, regardless of the mistake, regardless of the error. It takes a lot because I think just even in these past two years, we've seen more physical warfare. That's definitely come into my frame. We've seen pandemic responses that we've only drafted in plans and dealt with like swine flu back in the day or like little things. But now it's really that adjustment. So I like to quote Mike Tyson here - "I think everyone has a plan until they get punched in the mouth." And I think that first 100 days, we all have this glorious idea of 30-60-90. But in startup land, you have to be willing to adjust accordingly. And I think we're going to kind of touch on that a little bit more as we keep going. Yeah, definitely.

Rob Aragoa  05:22
I like the Mike Tyson analogy, getting thrown in there, appreciate that. Talk a little bit as it relates to when you're getting into startup land. You're at day zero, because you've gone through the process of kind of the mutual interview process, right, as you talked about the culture and understanding of what's real within that organisation, and what they're trying to drive at it kind of the key business outcome is what you're going to end up flipping back into how you're approaching it with your cyber programme overall. So let's talk a little bit about, you know, the approaches that you've taken, as it relates to getting to know what they're trying to accomplish, what the desired business outcome is they're going after to market and competition and all of that. And then how you kind of say, 'Okay, now this is how I'm going to take the steps and framing the way I'm going to enable them to achieve those things from my support in the cyber programme I'm going to initiate' or completely pivot from what they've actually had in place, maybe kind of explain about that. I think that'll open up the minds to people understand kind of the reality of how fast and important it is not to miss when you come in to a site startup.

Ty Sbano  06:39
Yeah. So I think when when you get there, you have the interview information, right? Like where or why am I even here? Like, what is the context for me being here? Am I starting at a series B, early enough where hey, maybe there are some good decisions, and I get to really build it from the ground up. We're more recently, starting in a series D. And it's it's different. There are things that are maturity wise, that look like a series B feels like a series B, but we got 300, some odd people running around. And there's a lot of processes that haven't matured at the same rate. So how do we prioritise? How do we think about that? And again, were you brought in at the right time? Or are you working, kind of on your heels trying to drive forward? And I think that's where you really need to understand who's your constituency? And what is the network of champions and change leaders that you're going to associate with? Or are you just going to be an army of one sitting in an ivory tower in the corner, because your security and it's like, I'll be honest, in startup land that does not work. You need to be integrated, you need to find the forums, you need to be invited to the forums, you need to be kept invited to the forums, right, like you can't be kicked out. And then also, I was like, well, why is security not good? Because I don't have visibility. Why don't you have visibility, where you don't invite me to meetings like that, that should be a telltale sign of like you're not fitting in? So the thing that I found very natural is getting as educated as you can in the business and defining 'what is the threat model? How are you looking at the world.' And I sit down with the executive and each company in the  very beginning to say, here's how I'm looking, you know, we can talk about business impact assessment, we've talked about all these buzzwords within security that, honestly, you as a CEO  you don't need to know. What I want to understand is when I prioritise things, or when I talk about a security incident, or I'm driving a business value change, like, hey, 'we're gonna go build on sales enablement, so we can fill out security questionnaires faster. So deals can close.' Everyone's  gonna go, 'Yeah, we want deals to close faster'. Well, here's the thing. We can't do that until we have a security programme. So if we start filling out questionnaires as quickly as possible it's like, 'well, we don't have this we don't have that we don't have this' maybe slow down on the whole thing. You know, and I think when you talk about that threat model of where are our functional risks, are we in alignment and agreement on what our exposures are, what our attack surfaces, and also the strategic roadmap? Give me at least two quarters, if I can have two quarters, great, but in most startups, you're gonna get like, two weeks, two months. Two years is not feasible. And I think when I look at my track record of previous publicly traded companies, having a three to five year plan was realistic, because you need it. You need to bring a lot of people along for that journey when you're security teams 350 humans. I got a team of seven right. Now I have it, I have privacy, I have some legal stuff. And I have security. And then I have this fringe thing called fraud, abuse, trust and safety that I don't have any time for, neither do my peers, but we're working through it. And we have a dedicated team. But strategically, we're not t kind of grinding there. And I think even in that communication, I have the confidence that I'm working on the right things. And I say 'this last thing that I mentioned, it's not a priority for me because we have some folks doing it.' I just can't jump in there because my skill set, my background, what I'm going to bring to the table for speed of execution is this stuff. And this is where we're going to drive forward and I think if you have that threat model firmed up, most folks will start to understand. So you identified additional gaps, you have an understanding of where we're prioritising, if you're elevating the right three things, right? And then any executive, you start getting into 5,10 20. And I bring a matrix like the NIST CSF, way too fast. No one cares. And I'm sorry to say this to all security professionals out there, they don't have time to care about it. That's your job. You need to communicate effectively to say, okay, of the things I've discovered so far. Here's where I'm focusing my time. Are these the right things? This is what it's minimising, this is what it's reducing. This is what you know what, maybe we just don't care. But one of the first acts I really liked to always pump for folks. And I got this from Mark Dorsey. He has over at Netlify.  And I met him at a meetup. And he just gave me really good advice. He's like, before we do anything as a CISO get an incident response retainer. And I'm like, you know what, that's always in my playbook now. Because when I get there, I don't know what I have. I don't know what I'm going to run into. And you know, what CISO wants to walk into the shop with that surprise of like, 'Hey, we got breached. And we didn't tell you about it in the interview process.' I know plenty of CISOs that have bounced from shops, because they were blindsided very, very much. And it's unfortunate, but that type of support with an incident response retainer gives you the confidence to say I can keep moving forward. And I have the backup and support in case something goes wrong. Because if I burn out in the first 100 days, and then where's your programme going, I couldn't tell you because I'm too tired, I'm exhausted. And I didn't sign up for this stuff.

Stan Wisseman  11:34
And also just, you know, you're setting an expectation and leadership saying, 'Look, something is likely going to happen even later down the road, we need to have something prepared just in case there is an incident so we can respond effectively and have in the right amount of speed.' So your communication is key with the executives, even before you join the company, certainly so the executives understand what the priorities are. But when you're looking at trying to quantify success, whether it be to the board, to the CEO, for yourself, are there some metrics that you typically are trying to capture? Or is it again, so dependent on the organisation, and in the context of what you're dealing with, there isn't a rule of thumb that you can go to,

Ty Sbano  12:25
I have a non standard metric. And while I appreciate KPIs, KRIs,  I think at startup land like you're you're shooting towards those trajectories, but in reality, you don't have the functional business processes, you probably don't have the people, you don't have the data.

Stan Wisseman  12:41
You can't feed them.

Unknown Speaker  12:43
You cannot feed your metrics without information. And I've been on both sides of this paradigm where metrics really influenced me in such a way that I've pivoted my career to go focus on bi and data for four years of my life. And it was very valuable, but like being data driven, is absolutely critical. But all that aside, when you're in startup land, or you're starting a security programme, if you start with metrics, I think they can be inspirational, but you're going to lose your audience, because you're typically in a fast moving shop that wants to realise value. And to get to that value statement. You're talking about nirvana. And it's not feasible. So MVP, or minimum viable product, I know it's an overused word. But where can you start small and get your key wins while you're building your strategic wins to get to the next phase? And my question is, is simple. Do people want to work with me and my team? If the answer becomes 'No', well, I'm not doing my job. I didn't show up right. I didn't present right. Or maybe this company just didn't want me to be here. But I can tell you, in the interview process, once again, before you sign up for any of these gigs, you should have a clear established idea of like, what am I there to do? There to disrupt a lot of stuff and piss off a lot of people? Well, I want my contract, I want my work agreement to reflect that. Because if I'm there for one year, I'm not going to be able to do a multi year journey. My preference is to find the place where I'm in a multi year journey. It's really important to understand why you're there. So even before that point of asking that KPI and that metric, like having that defined success criteria of like, what do you expect me to do by the time you're one rolls around? And if there's no answer, or it's like, well, you're going to tell us. I love those. I love when I get hey, you're going to help us inform what is it that we're going to measure and why, and success or not? Because if you're getting compromised every day, and no one cares, then 'whatever'. But if you get compromised once and you get fired, then it's a different story. Right?

Stan Wisseman  14:38
And I just following up on that. I do agree in that context of if they don't perceive value in that, they're not going to invite you to that meeting. But going back to your experience for the whole product security side of the house. In your role as CISO to a startup that's coming up with a product or service, you're trying to ensure that your organisation is secure. But you also have a more than most awareness of the importance of ensuring that whatever product or service you're offering, is not going to introduce risk to your consumers.  Looking at your perception of success, or where you need to focus your time, how much of it typically is on the organisational side versus what you're providing, as a service or product?

Ty Sbano  15:28
Yep, it depends on kind of the product itself. And it also depends on why I've joined. If I'm starting with the base programme build, which is something I'm doing at Vercel now  starting with a lot of the enterprise controls, but I brought in someone that I've worked with in the past , an amazing security engineer ,we've done some of this journey together in the past that I can say, Cool, you go work with product. You know, I'm here, like, that's all I've ever really done. And I love to do, and I prefer to do that work, but I can assist you and watch, you get that part done too. And in all honesty, it's not at the executive tier that the product really moves. And that's, that's a difference in my observation as well. Like, yes, I can help. But if I'm sitting down to explain, like, you know, here's how we're gonna establish DDOS protection within our product to sell this to customers. I don't talk to the executive team too much about that. I'm talking with the directors, the product managers, the sales team. I'm working cross functionally across the org. Good and bad C-level titles can do some of those things. But when we pull a lever, say we have something really bad secrets, management isn't good. You know, I've actually I can say this out loud. Most of the shops I've ever been at Secrets management can be great in certain areas. It's not great everywhere, right? And we all know that that creds leak, creds go to the wrong place. Sometimes it's just speed of movement that has to get something done and I text slack it to you DM it to you over LinkedIn, whatever it is. Sometimes we have to take those degraded stances. But when I when I look back at like enterprise versus product, I don't always kind of conflate the two, because if I'm charging after the basics of hey, what third parties do we have in our shop? What end points do we have for all of our employees? And if I can't answer that, why am I gonna go narrow and deep on the product to build out these crazy cool features, that is going to empower the journey and help sell this more. When we all know massive breaches and issues really occur from basic flaws?  2FA, the most recent one that's out in the news with I forget how many billions of people's information, that that was from a blog post. And it had a secret in it, and someone recovered it. And then now they've extracted this and they're selling, you know, billions of billions. Now, that's the perfect storm, an example of like, well, we could have did all this great stuff and the product, but they didn't actually matter.

Rob Aragoa  17:58
You know, you kind of hitting upon where I want to go next. And it's about the  positive security culture. Alright, so establishing that. You talked about, you know, your meeting and engaging with the different directors, the product leaders,how do we go to market with our solutions? How do we ensure that people are thinking about security as you're creating the different products and services and capabilities to continue to grow Vercel.  You talked about  quick, visible wins, 'here's what I'm thinking about doing. We agree that we should achieve these things' and you achieve it or over achieve it. So you're show that positivity back right to the business. But when you think about kind of instilling that positive culture across the board, it's not the easiest thing, right? What are some of the things you've seen work? What are some of the kinds of, you know, lessons learned as well,

Ty Sbano  18:50
I think it's as simple as carrot versus stick. You know, there was a really powerful book called The Carrot Revolution and The Carrot Principle that I kind of read way back maybe 12 years ago, 10 years ago. I really appreciate the sentiment there. Because I think one of the things that we've already talked about is coming in on the tail end of a rough team, or maybe a team that's already in place. I think that's been one of my magical behavioural traits that has allowed me to excel within the security space. Because a lot of folks come into this with that negative view or very critical or their traditional curmudgeon security person. It's not customer oriented. And I think as someone that started purely in consulting, you have to put your best foot forward, you're there for the customer and that ideal that everyone is your customer changes the narrative. So I think when you treat your employees, your folks within your company,  your direct reports as customers of your service, it changes the narrative. And I think that's something we have to think about. So going back to that previous question, like do people want to work with me? I consider that too with people that report to me, and sometimes the  long ones that are on the ship have to hear the message over and over. And they're like 'Why is this person so positive? Like, why do they focus on this narrative or these data elements to drive change versus like, telling people it's really bad.' I'd rather have that conversation internally as a team, then go and lambaste someone. So even as something as simple as a security incident where someone falls victim to a phishing attack,  when you do phishing training, do you end up firing everyone that clicks on the link? Right? Like when I hear those stories, I cringe. Because I'm like, that's not a learning moment, you're actually dispelling trust. So the element there for me is like, I'm trying to establish trust in so many of these customers that it only takes one mistake, and only takes one miscommunication and takes a lot of this. So going slow to go fast is really important. I firmly believe in going extremely fast, but with respect with positive intent, and I think that resonates back because people trust you. And when people trust you, guess what happens? They self report issues, they fix issues, they partner with you on things. When they don't trust you they don't want to work with you, you don't know what the issues are, you'll never know what that tech debt is. The skeletons remain buried somewhere behind you. Stay in your ivory tower, right? You're in our way. And then you can literally have that conversation with the frustrated engineers, the directors that are pointing and saying, 'well look at how crappy these people are in the security space'. 'You know, like, that's cool. I'm not them,' you know, or 'that's cool. That was in the past.' And that's something I'm battling right now is like, that's in the past, let it go. Because I don't care anymore. That was six months ago. Do we talk about that six months old? Not a lot. So why are we talking about people that haven't had any impact on what we're doing now, today? I've rewritten the policies. I have adjusted the programme, I'm talking to our customers, like I'm doing all this stuff. Why back reference? If there's context setting, I'm so down to have that conversation. But if it's just to talk crap. I get one or two with me, I just, I don't want to have a third round of like, I just want to hear someone just getting bashed, it's like, you know, they probably had some positive things. Maybe they weren't set up for success. There's a lot of contexts I don't have either. And we're hyper focused on something that's not building support. So I think when you really focus on for progress, and always focusing on that step forward, like, it just changes your mentality. And I think a lot of folks see that and want to work with that. Because that's, that's the type of person I want to work with.

Stan Wisseman  22:37
Well, hey, you know, this podcast, what we're doing is about  how we can adapt, what we've been doing, to do it better, and be able to honestly handle today's threat landscape and business landscape, right. And you're all about adapting and evolving, as we've been talking about. So in that broader context of cyber resilience, how can we evolve what we've been doing for four decades on cybersecurity to address today, and tomorrow's new threats. What do you think? What's next, where do we need to go?

Ty Sbano  23:16
I think it's a continued movement towards actually less talk of injecting the word security into things. So I've been stuck on this my whole career. And it started with application security with this idea of a secure SDLC. So when we say 'hey, we're gonna go in a secure SDLC.' Does that mean everything else is insecure? And it's happened again, in my opinion with DevOps Well, we're going to do DevSecOps, I'm like, well, I mean, DevOps already has quality into it. If we've all agreed that security is a subset of quality, then we don't have to have this conversation. And we're doing it again, you know, secure cloud, cloud security, posture management. It's just posture management, right? I get it, I understand from the marketing side, I'm on this side of the sale now in startup land compared to like, publicly traded where you know, it's too big to fail. It's a very different scenario to understand the business model for what it takes to make a sale. And I get the search engine optimization, I understand why we have to have those words, but as practitioners inside of your four walls, if you're beating down the door, and always saying security, special security's unique. Well, I think you're becoming anti resilient, because you're creating these different tracks, you're creating these different places of documentation, creating a different communication style. My recommendation is to be part of the resiliency strategy that's already there. It's not to break away and create something new. And I understand sometimes there's disambiguation that has to happen with like incident response or security versus incident response for like PR and other things, which you may get involved with. But I really go back to just like dropping the terms of cybersecurity from those narratives and just talk as if I'm with the business, because I am.

Rob Aragoa  24:12
I think that's spot on. It's one of the things for me that. It's DevOps. There's no Sec in the middle, because once you put that in the middle  just kind of distinguishing that there's some sort of separation, we need to kind of have a conversation and debate where we come in. No, no, no, it's built in. It's baked in. Just to your posture management example. So  I agree with that principle. Because it does set the stage correctly when you're initially engaging with the other audience that is used to doing their things. And now it's simply kind of embedding the elements of security just into it as part of the equation.  We appreciate you coming on and sharing your journey from the really large organisations to the kind of the focal areas you've been going after in startup land. But the approaches that you've taken is what I hope the listeners really take, as lessons learned, different ways to work with the teams to help enable those positive security cultures and drive really programmatic success at the speed a startup has to move at to be able to be a successful organisation  grow. So thanks for joining us to Ty.

Ty Sbano  26:05
Appreciate you having me always happy to chat.

Stan Wisseman  26:07
Anytime. Thank you.

Rob Aragoa  26:10
Thanks for listening to the Reimagining Cyber podcast. We hope you enjoyed this episode. If you would like to have us cover a specific topic of interest, feel free to reach out to us and you can find out how in the show notes. And don't forget to subscribe. This podcast was brought to you by Cyber Res,  a Micro Focus line of business where our mission is to deliver cyber resilience by engaging people process and technology to protect, detect and evolve