Resilient Cyber

Nikki - First - tell me a little bit about yourself and your background  Nikki - You have a ton of experience with the Army, can you talk a little bit about what you like most about working with the military and specifically in HR? Chris - We hear a lot about digital transformation in the DoD, Cloud, Cyber, Zero Trust, and so on - but how critical do you think the workforce is to make all of these transformation efforts successful Chris - We know the DoD has historically struggled to attract and retain technical talent. What specific changes do you think are needed to help resolve this challenge and do you think we're making any headway there? Nikki - One of your previous roles was Deputy Director of People Analytics, I've not heard much about this role before and I'm interested what that type of position entails and what that means to the people in an organization? Nikki - I want to talk to you about health, fitness, and wellness when it comes to IT and cybersecurity positions. There is a ton of research around the burnout and stress that technical positions carry - what can we do to help our technical teams? Chris - I have seen you posting and speaking about the role AI is playing in assigning resources, assistance and leadership to various Army cohorts, what are your thoughts on the role AI is and will play in your area of expertise?Chris - I believe there has been a new Army vision for the future of talent management, can you tell us a bit about that and what it entails? Nikki - Can you talk about the integration of AI/ML into both HR and administrative functions? I could see how beneficial it would be and free up some cycles to focus on the people and their wellbeing. Nikki - Can you talk about some of the other innovation in the HR space?

Chris: I have been following your research for several years now, dating back to your role before Chainguard. As you have watched the conversation around Software Supply Chain Security unfold in the industry, do you feel like we're making positive headway?Chris: You have done a lot of research into software supply chain security, and of course SBOM's. One recent study you took a look at the quality of SBOM's in the OSS ecosystem, compared to say the NTIA defined minimum elements for SBOM. Can you tell us a bit about the study and implications of the findings?Chris: In addition to SBOM, we're seeing the emergence of VEX, can you speak a bit about its importance?Chris: I wanted to follow up about OSS, since it has become such a core aspect of the software supply chain conversation. I'm sure based on your studies you know the phrase dubbed Linus' Law, which states that "with enough eyeballs all bugs are shallow" but based on my research for writing a book recently, I realized that the overwhelming majority of OSS projects lack enough eyeballs. Do you think this is a challenge when we look at the widespread adoption of OSS?Chris: Can you tell us a bit about your next/current efforts for software supply chain security research?

Chris: Before we dive into some technical topics and questions, we would love to hear a bit about your background and careerChris: - We've now seen the introduction of JWCC into the mix after quite a challenging road to get there. What major changes do you see JWCC playing in the DoD cloud landscape and cloud adoption journey?Nikki: - There's been a tremendous focus on software supply chain security, with a 742% increase in software supply chain attacks in the last three years. What are your thoughts on how the DoD is approaching securing the software supply chain, SBOM's and challenges of that nature?Chris: - We know the DoD CIO office published an Open Source Software (OSS) memo not too long ago. What role do you think OSS plays in the future of the DoD's software and warfighting capabilities?Nikki - We've seen a blossoming ecosystem of software factories across the DoD, now numbering near or beyond 30. How key do you think these software factories have been to the DoD's software modernization efforts?Nikki - I would be remiss if I didn't ask you about the DoD's workforce challenges. We know the DoD has had long standing issues attracting and particularly retaining technical talent. How crucial is remedying those workforce challenges to see successful cloud adoption and software modernization?Chris - Being a longtime Federal and DoD Cyber professional I have to bring up the topic of compliance, RMF and ATO's in any discussion around fielding software. We've seen a push from some senior leaders to try and shift to a culture of cyber readiness and alleviate some of the traditional box-checking/compliance culture we know is pervasive across Government. Any thoughts on how we can modernize Cyber and Compliance in DoD to facilitate getting innovative and modernized software-enabled capabilities into the hands of system and mission owners?

Nikki - With your experience in various cloud and Cybersecurity roles, what would you say the top 3 concerns are right now for cloud security? Nikki -  I see you do a lot of work Cybersecurity and cloud education, do you feel like we have better tools and resources today than a few years ago? Or too many resources? Chris - We know you have a Detection Engineering background. For folks not familiar with Detection Engineering can you tell us a bit about it and the role it plays in Cloud Security?Chris - It is often said that Detection Engineering builds on the practice of Threat Modeling, in terms of identifying relevant threats and building detections associated with those threats. Do you agree with that and how valuable do you think Threat Modeling is for Cyber and Cloud Security professionals?Nikki -  What would you recommend for anyone getting started in the cloud, moving from on premises or data centers, what should they do first? Nikki - What do you think is next for cloud? I see so many debates in the industry and it seems like there's a trend towards creating systems on prem versus in the cloud.Chris - I know in addition to your professional role you've a huge content creator with over 20,000 folks following you on YouTube. How did you get going down this path?Chris - Do you think it is important in the current industry landscape and remote work paradigm to be out there building a personal brand, creating content and engaging with the community?

Chris - I have to start with the intersection of law and cybersecurity. We're seeing major strides in regulations, both federal and state (like NYFDS), to regulate and enforce cybersecurity policies and program-based guidance. What are some of the emerging trends we're seeing in cyber law? Chris - As you know, we recently saw the new National Cyber Strategy, which makes a push for shifting the burden/responsibility for cybersecurity on the vendor or those best positioned to address it. Why do you think it has taken us so long to get to this point? I know you've drawn parallels to other industries such as automobilesChris - On the topic of parallels to other markets and industries, such as automobiles, pharmaceuticals and manufacturing, there are some unique aspects of software, in the sense it isn't tangible or kinetic, and can be very opaque, What impact do you think those characteristics have on trying to regulate it like we have done with other industries?Chris - The National Cyber Strategy also introduces the concept of Software Liability. This part of the strategy got the most aggressive response from industry and the community. Why do you think this makes everyone perk up so much?Chris - Many started to raise questions such as who will define "secure", who and how will it be validated or verified, and where is the line of responsibility between the software supplier and consumer. Any thoughts on these topics and questions?Chris - On the topic of regulation, many consider cybersecurity to be an example of a market failure. Can you explain what that is, and why some feel that way? How do you think think we balance regulation without stifling innovation in the tech industry?Nikki - How do you think the public sector and private sector are seeing cybersecurity laws differently? Do you feel like the private sector is lagging behind in cybersecurity regulations? Chris - I have worked on programs such as FedRAMP before, for Federal Cloud Services and I am familiar with NIST 800-171/CMMC as well for the DIB. Many argue, and I think there is merit to the claim that these sort of frameworks lead to smaller pools of suppliers and potentially a less diverse pool of market participants. Any thoughts on these impacts and if it is worth the trade off?Chris - Many compliance and regulatory schemes either take one of two approaches. The first being a self-attested model where entities self-attest their compliance, such as NIST 800-171 for the DIB was, and the second is a 3PAO model, where a 3rd party verifies compliance, such as in FedRAMP. Each of these models has drawbacks, such as less than truthful or accurate self-assessments, or the 3PAO requirement becoming cumbersome, costly and a bottleneck. What do you think about these two approaches and where do you see us heading with regards to say the National Cyber Strategy, liability and so on?

Nikki: I have to start with an article you wrote a couple of years ago, about how we explain and provide context around vulnerabilities. I love the analogy of a 'vulnerability recipe' and how we can step through an explanation of vulnerabilities. Can you talk a little bit about the process and what compelled you to explore this topic? Nikki: I saw you spoke to Ron Ross recently, we had him on the show last year talking about cyber resiliency and of course software supply chain. Can you talk a little bit about security assurance and what that means to both developers and security practitioners? Chris: You've been a leader in the AppSec space for some time, particularly focusing on capabilities and tooling such as IAST. For folks not familiar with IAST, can you explain what it is and the value it adds over say SAST and DAST?Chris: I know you and I have exchanged messages and comments about Software Supply Chain Security and SBOM. What are your thoughts about where were headed on this front as an industry?Chris: With the release of the National Cyber Strategy yesterday I of course have to ask your initial thoughts. First more broadly, about the overall sentiment of the strategy and also about specific areas, such as increased requirements on software vendors and technology providers to produce secure products and the potential for increased liability.Nikki: It looks like you had a pretty lengthy time with OWASP - can you talk about some of the work you did there and the work that OWASP does? I think people typically equate OWASP with the OWASP top ten, but there are so many free resources and tools available for developers and security professionals. Chris: Given your past involvement of a decade with OWASP in its early growth, any thoughts on the recent open letter we saw sent to the OWASP leadership?Nikki: Can you talk a little bit more about Contrast security and the type of work you all do? Would like to hear more about what the company has going on and anything else you may have coming up.Chris: Continuing on with Contrast, I am interested in the founders journey a bit. Contrast has been around for nearly a decade and is now up to several hundreds of employees. What has that journey been like and what are some of the major ways the industry has, or hasn't changed during that time?

Nikki: I saw you recently did a Cyber Jeopardy Panel at the American Bar Association about cybersecurity and cyber law - can you talk a little bit about the intersection of cybersecurity and law?Chris: Continuing on that thread a little more, and you and I have chatted about this, what are some of the dichotomies or challenges of Cybersecurity in a democratic society versus say an authoritative regime or nation?Chris: I know you have a background with the DoJ and U.S. Attorney's office, are there some challenges with say cyber investigations in the U.S. due to some of our protections for individual freedom, privacy and so on? Nikki: It seems like we're seeing more and more organizations seeing the need for both mature cybersecurity programs and cyber law programs - but I haven't seen a ton of these groups working closely together. How can we build both programs in combination?Chris: It seems like every day we are seeing headlines about catastrophic cyber incidents.  Are there any historical parallels to what we are dealing with today?  Do you think we’ll ever get out of it? Nikki: What do you think major attacks like ransomware in healthcare and even in local and state governments and school are doing to shape cyber legislation?Nikki: If you could give one message to the American people about how we will address this challenge, what would it be?Chris: I would be remiss if I let you off the show without trying to dig into the forthcoming National Cyber Strategy with you. With the extent of what you're able to share, there's been a lot of buzz and rumors about an increased call for regulation, do you have any thoughts on that front?Chris: Many have said that Cybersecurity is a market failure and that it will require government intervention and regulatory measures to change things and have cybersecurity be taken more seriously by businesses and organizations. How do we balance that need for truly addressing cybersecurity risk without at the same time stifling innovation and our free market society?  Nikki: Do you see more legislation potentially coming in the future around security governance and compliance?Nikki: I'm very fascinated by cybersecurity and law terminology - do you think there's some room for us to find a common thread between both disciplines to help people like me understand law terminology and language better?

Chris: First off, why do you think soft skills are so often overlooked or undervalued in our field of cybersecurity?Chris: I'm curious your perspective on how to help people build soft skills, much like technical skills, some may have more of an aptitude for technical work or prefer not interacting with people as often. Any advice for folks who may be a bit more of an introvert and finding dealing with people intimidating?Niki: I wanted to first talk about the Learning resources you have on your site - the softsideofcyber.com - I am a big fan of this area because you include everything from books and articles to newsletters. Can you talk a little bit about why you included this section and what you're hoping to do with it in the future? Nikki: This may seem like a silly question - but clarity and definitions for terminology and language are really important. People talk about 'soft skills' in a lot of ways. What does 'soft skills' mean to you and how have these skills aided you in your career? Nikki: What is the perfect balance of technical and 'soft skills' - do you feel like it depends on your role? Or do you feel like this balance is essential, regardless of your role? Chris: You recently wrote an article on CSO online about unleashing the power of an effective security engineering team. While you did discuss technical skills you also wove in content from folks such as Sidney Dekker and Adam Grant. How do you feel like diversifying your learning outside of technical topics has helped you be more successful in your own roles and career?Nikki: Do you feel like 'soft skills' expands from empathy and emotional intelligence to an understanding of cognitive bias, mental workloads, and other psychological phenomena?Chris: What's next for the Soft Side of Cyber? What projects are you working on and what are you hoping to do with this in the next 6 months?Nikki: Since I know what cyber resiliency means to you in a technical context, can you expand on what this means to you in the 'soft skills' and human context?

Nikki: My first question is about your book, The Application Security Handbook - who do you think most benefits from this type of book and why do you think they need it?Nikki: What inspired you to write this? You have a ton of experience from being a security architect, to working in an IAM group, to application security - I would imagine all of that expertise allows you to see application security through a unique lens.Chris: In your book you touch on the dichotomy of shifting security left while minimizing friction between the Security and Development teams. This is a common challenge many security teams face. Can you elaborate on some of your recommendations on this front?Chris: You also emphasize the role of security champions and democratizing security to some extent through this approach. What exactly is a security champion and how do organizations go about doing this?Nikki: You mention threat modeling in your book - what do you think is the best place for Application Security programs to start when building in threat modeling? This is typically a higher level of maturity for programs and I'm curious at what time it's best to integrate threat modeling?Chris: We're obviously seeing a big push for robust CICD pipeline tooling for security such as SAST, DAST, SCA, Secrets Scanning and So on. Of course this tooling all produces noise. You lay out some strategies in the book on dealing with that. Can you touch on some of those here?Chris: I would be remiss if I let you go without discussing Software Supply Chain Security and SBOM's. I know you touch on SCA, OSS and SBOM's in the book. Why do you think it is key for organizations to start including this in their appsec programs? Nikki: What do you think are the greatest concerns when building a mature application security program? What are the biggest impediments? Nikki: What does cyber resiliency mean to you?

- Can you tell us a bit about the book, what made you want to write it and how you settled on this topic?- Historically IT and Security have been at odds, often feeling like the other party is conflicting with their goals and responsibilities. Why do you think this is?- Do you think the push for DevSecOps and breaking down silos between Security and Operations (and Development) has helped at all?- Your book talks about emotional intelligence, empathy and non-technical traits. How critical do you think those are in this situation and why do they not get discussed enough?- What methods do you think IT and Security teams can take to improve their relationships and drive towards a unified outlook and goals?- What do you see as the biggest gaps on this topic as we move into the future?