How to be a CIO of not one, but two fortune 500 companies

Mike Kail is formerly the CIO at Netflix and Yahoo! For his most recent challenge, Mike has moved to a startup take on the role of CTO at Mike is a bay area resident and has been a technical advisor to many startups in the area.

**Please note that this interview has been abbreviated for this blog.

Mayank Mehta: Hi everyone. I am Mayank, the co-founder and CEO at Pulse. We are privileged to have Mike Kail with us today. Mike has had an amazing career. From being VP of IT at Netflix and Yahoo, to being an early stage executive and CTO at Everest – Mike has seen it all.

Mike Kail: Thanks for having me.

Mayank Mehta: Let’s jump right in. Start of by telling us, what led you to becoming a CIO?

Mike Kail: There was no masterplan. I started as a Unix SysAdmin and thought, I need to move my career forward. After which, my life has been long game of no limit Texas hold them – try to make the most of your hand. There is a bit of timing and luck involved for sure.

Mayank Mehta: There are a ton of VPs and Directors that are also part of the Pulse community that are trying to emulate the sort of growth and trajectory that you’ve had. What made you stand out as a leader amongst your peers?

Mike Kail: It’s not just an individual effort. It’s definitely a team effort. So hiring really great people and enabling them is a big component of looking better yourself and being able to advance. It’s also making some big bets and taking some risks on emerging technologies. Speak up on what you think the business should do or how it should evolve instead of staying stagnant. The bigger the risk, the bigger the chance to win.

Mayank Mehta: With immigration barriers going up and with salaries on the rise, how are you thinking about hiring? What advice do you have for CIOs that are looking to create world class teams?

Mike Kail: I look beyond just the technical skills. By the time they reach my desk, I am assuming their technical chops have been tested. I don’t do the Whiteboard programmatic interview, which is kind of the old school Google thing. What I am looking for is what is the intrinsic motivation of the person, what makes them tick? I always look out for trail blazers but with some self restraint and self awareness. I think you get people when you create an opportunity for them to grow and show them that! You’re never just hiring for a static role.

Mayank Mehta: How do you find the self starter from let’s say 100 resumes?

Mike Kail: It’s really about having a conversation with the person. I want people that are self aware enough to know that they’re interviewing me and the company just as much as I’m interviewing them and having that confidence to ask probing questions, and kind of push the envelope during the interview.

Mayank Mehta: Which communities/ networks have been most helpful to you and how have they helped you in your career?

Mike Kail: First there is Pulse. The community has been helpful, and fun to engage with because it’s a safe zone for people to ask questions and we can all give direct, transparent, candid answers.

There’s a weekly #CIOchat on Twitter that a group of really smart individuals take part in. I also try to get involved with the venture capital community which we’re fortunate enough to have here in the Silicon Valley. My interactions help me understand what they’re seeing – what are the major trends to be aware of.

Mayank Mehta: How did you first get involved in helping startups and how do you pick who you’re going to work with? 

Mike Kail: Given my “Dev ops” background, I’ve always been really excited about emerging technologies and how to do things differently and kind of look out ahead. When picking a company, I have to be excited about what they’re doing, but more importantly actually give advice that is helpful to the company. I am not interested if the advice I am giving is not actionable.

Mayank Mehta: How do you think CIOs, CTOs should work with some of the younger companies to mature their solutions in parallel to making sure that they’re not compromising, especially with the breaches that we’ve seen recently, their stakeholders and company integrity?

Mike Kail: I think both parties need to go into the potential engagement with eyes wide open and understand the risks, but also understand the opportunities. CIOs should understand that they have a chance to actually shape the direction of whatever product, or platform, or service to meet their needs more rapidly than somebody else. And you don’t want to take them down a very narrow path, but you have early influence and you have to establish or create this partnership, not a vendor client relationship. That’s really important.

Mike Kail: Keep a tight communication loop and let them know very candidly what is working or what isn’t working and what needs to change. But I think startups, once again, entrepreneurs, we all become very enamored with their technology and don’t think about the issues and pain that it sprays out once it’s deployed in a more broad enterprise. So, have those direct candid conversations without being disparaging.

Mayank Mehta: Again, talking about startups, one of the questions from the community – How do non Silicon Valley IT executives keep up with the pace of change? And even just starting with you, how do you keep up with the next thing out there and stay ahead of that curve and then how do you recommend others do the same?

Mike Kail: Once again, join the Pulse community. This is not a plug! I actually think there’s a lot of conversations going on about our new initiatives. Like we had a conversation yesterday, somebody who’s working for a nonprofit and trying to figure out what cloud database to use. There’s a myriad of answers but it gives them something to think about that maybe they didn’t. The other channels once again are Twitter or I think there’s a few slack groups and then attending some conferences. Stick your head out there and see what other people are doing versus suffering in silence and say oh, I’m not in Silicon Valley, I can’t do anything. Location should not inhibit innovation and efforts around that.

Mayank Mehta: Another community question. If you had an enterprise easy button to change one thing in your company, what would it be?

Mike Kail: The technology is the easy part. My button would really help teams create clarity and ensure that everybody is working in concert to move the business forward versus fighting for their own fiefdom or personal desires.

Mayank Mehta: That does require a big easy button. Okay, next …

Mike Kail: Maybe the easy button is a bit of shock therapy.

Mayank Mehta: Okay. What are the trends to be aware of in 2019, both in security and outside of that, the ones you’re excited about?

Mike Kail: To be frank, it’s really hard to get excited about security anymore. Everybody comes into and out of RSA extremely excited about the newest, hottest, the innovative companies. Yeah, the security overall is abysmal at best.

Mayank Mehta: Really? Why do you say that?

Mike Kail: I still think there’s a lot of common approaches and mentality just repackaged. So we’re still talking about Next Gen Firewalls, Next Gen Endpoint Solutions, the magic of AI solving it all without going back to core engineering and figuring out that the application is a huge attack factor and the common exploits have been the same for the past 20 years. Projection and cross site scripting are two of the top 10 vulnerabilities still. We’re not getting better. It’s hard to get extremely excited about approaches. But having said that, I think there’s a few initiatives. One that I’ve been involved with for the past few years is around zero trust security. How do you flip your environment on its head and assume you have zero security? What would you do to make it more resilient and have more visibility into that environment or application versus trying to keep layering on solutions to harden it. Meanwhile, the core is still very squishy.

Mayank Mehta: We’re heard this before. Folks are still saying things like “Hey, phishing is still like a huge problem,” How is it that in 2019 and phishing is still a problem? What is causing that to still be an issue? Is it some of the legacy components out there? Is it a cultural issue where email and still treated as just like easy thing? How should CIOs, CSOs think about this?

Mike Kail: I mean I think everybody is vulnerable at some point. We’re all extremely busy. You’re going from a laptop or desktop to mobile. The phishing attacks, they’ve gotten much more sophisticated. So it’s really hard to tell without digging into the headers of the email message or examining the links and shorten URL is make this a little more challenging, especially on mobile. But I think it’s really about ongoing training and awareness of how to prevent this. I think the large scale email service providers like Google and Office 365 with Microsoft have to get better about detecting this and scanning without compromising privacy and data

security of course. But it’s about this continual awareness and not scaring people.

Mayank Mehta: Agreed. Okay, if you were to start a CSO, CIO role today at Fortune 500, what are the first 100 days look like for you? And making sure you’re not a headline on Fortune in the wrong way?

Mike Kail: Wow. That is a stressful first 100 days. I think the first thing is you really have to go around and kind of assess what the security knowledge of the company is. And then look at common things like how are your printers secured? There’s a bunch of simple things people forget about that anybody can walk in and unplugged the printer Ethernet port and plug a device in and start sniffing network traffic or having unfettered access to production systems because they’re on the same virtual LAN. Looking at the real simple things before you dive into the media topics. Going back to what I said – really working with the engineering team or if you’re developing an application or service, what are their current ways of doing security testing and assessments and moving them into a culture where security is a first class citizen in the software development life cycle.

Mayank MehtaYeah. Makes Sense. Are there companies, Mike, that you’re excited about in particular in this space that you’ve seen up and coming or even some of the more established ones with newer solutions?

Mike Kail: I think Cybric is doing great work. I have been involved with them. There’s a few others doing container security and intent based security. I think those who were taking his software perimeter-less approach are probably more relevant and future proofed.

Mayank Mehta: What are the things you’re excited about in AI and ML having real impact versus being “buzzwordy” for now?

Mike Kail: Wow, that’s a tough question. I saw some recent headline that 40% of companies claiming to have AI solutions, really don’t. As IT leads, we need to dig down. Ask serious technical questions like what machine learning model are you using?

Mayank Mehta: We’re actually going back to leadership questions now. We constantly hear that CIOs are starting to play more strategic roles in organizations. How should CIOs actually think about doing that? Is a top down, bottom up? What does that transition look like when you go into a legacy company where truly IT is treated like it’s back office?

Mike Kail: I think the first c-level colleague to collaborate with is a CMO because you have to take a marketing/ rebranding approach. I think IT/ Information Technology really should be rebranded to be digital technology. If you think about the Buzzword of digital transformation and moving to a digital world, information is going from analog to digital. So the organization needs to have that mindset. We need to instill that in the entire company, that this isn’t a back office service desk help desk. It’s actually providing the core foundation for the company to deliver value to its internal and external customers.

Mayank Mehta: Okay. How should CIOs think about positioning themselves to be board ready, be noticed. Is it through headhunters? Is it through a colleagues? Is it through networking? How do you approach this starting from zero?

Mike Kail: I think it’s really about networking and it’s about establishing yourself as not just being a digital technology leader, but that you understand the financial aspects of business. Then go to sales and marketing, all of the other core components that digital technology drives but isn’t directly involved with because you can’t be a great board member if you’re not well rounded. You can’t just think of yourself as the “technology expert”. You’re probably not ready to be on a public board if you do.

Mayank Mehta: So let’s use an example. You’re sitting in a Fortune 500 board, how do you explain to the rest of the team what 5G means to their business? 

Mike Kail: I think depending on what business you’re in, you have to relate it to the customer experience and how it ultimately drives revenue and increased engagement. So for 5G specifically, I would say: “Okay, I can have more rapid interaction with my customers, whether it’s them coming into a storefront or us having an augmented reality experience that’s powered by the edge and 5G.” That’s just one example, but you have to make it relatable to them. Otherwise, they’re going to tune out if you go into the technical details of a 5G network, they don’t care. It doesn’t matter to them. The street doesn’t care about that. No one really cares except the technology people behind it. Relatable is the key thing to keep in mind.

Mayank Mehta: Yeah. Working backward from customer experience makes a lot of sense. So you’ve obviously transitioned successfully from being a very senior executive in a number of amazing companies into now successfully running and being part of multiple startups. How was that transition for you both from a cultural perspective and day to day operations perspective? 

Mike Kail: Exciting, stressful, overwhelming, all of the above. I think you go from a large company with a big support structure. A fantastic Chief of staff, to really, well, being responsible for everything. And you have to be able to adjust and adapt to that. The buzz phrase “Be comfortable being uncomfortable” and having that on a daily basis and not knowing everything. It’s certainly not a journey for everyone, but if it excites you, I encourage people to try it.

Mayank Mehta: Yeah. Tell us a little bit about Everest, Mike. What got you excited to just start working on and what are you guys building?

Mike Kail: Everest is not an enterprise play, which is exciting to kind of get out of that world and into more of a global fintech platform. Everest is allowing us to move further into the concept of self server identity, which is user controlled. So getting away from centralized databases that are siloed to a centralized infrastructure where each user enrolls and has their own identity that’s managed by them with their own biometrics. So it’s not a small undertaking. And it’s still early days, but there’s a myriad of use cases including helping the 1 billion plus people in the world that lack true identity and the additional one and a half billion that are unbanked because of lack of identity or lack of resources or true credit score.

Mike Kail: So now with our distributed ledger, you can build up your own transactional history and it’s verifiable by your identity. So I’ve used the concept of, you have a passport, now I get stamps when I do something good or visit a country or perform a transaction. That’s immutable and verifiable.

Mayank Mehta: A good use case for blockchain for a change.

Mike Kail: Change one component of the system and it’s actually not an extremely large component of it. People think, oh, I’m going to deploy blockchain and it will be magic and it’ll solve all these problems. If you try to use it as a database that your project will fail pretty miserably, pretty quickly.

Mayank Mehta: Mike, this has been so great! Thank you for all your time.

Mike Kail: Thank you for having me!

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