Category: Organization

Security Considerations For M&A and Divestitures

I’ve been speaking to security startups over the last few weeks and some of the discussions made me think about the non-technical aspects of security that CISOs need to worry about. Specifically, things like mergers, acquisitions and divestitures and the different risks you will run into when executing these activities. There are a number of security issues that can materialize when combining businesses or separating businesses and in this post I’ll share some of the things you need to think about from a security perspective that may not be obvious at first glance.

What’s Going On Here?

There are a number of reasons for mergers & acquisitions (M&A) or divestitures. For the past two decades, the tech industry has used M&A to acquire smaller startup companies as a way to collect intellectual property, acquire specific talent or gain a competitive advantage. Divestitures may be the result of changing business priorities, separating business functions for regulatory reasons, eliminating redundancies or a way to sell a part of the business to cover costs. Mergers, acquisitions and divestitures are similar because you will want to review the same things from a security perspective, but it is probably easiest to think of divestitures as the reverse of an M&A – you are separating a business instead of combining a business. Divestitures are definitely less common than M&A in the tech space, but they aren’t unheard of. There are also differences in terms of the security risks you need to think about depending on if you are acquiring a business or separating a business. My best advice is to work with the legal and finance teams performing the due diligence and have a set process (that you have contributed to) so you don’t forget anything. With that, let’s dive into a few different areas.

Physical Security

Physical security is something you will need to think about for both M&A and divestitures. For M&A you will want to perform a physical security assessment on the facilities you are acquiring to make sure they meet or exceed your standards. Reviewing physical security controls like badging systems, fencing, bollards, cameras, fire suppression, emergency lighting, tempest controls (if required), safes and door locks will all help make sure your new facilities are up to standard. If you aren’t sure how to perform this, hire a company that specializes in physical security assessments or physical red teaming.

While physical security for M&A may seems straight forward, there are a few gotchas when performing divestitures. The biggest gotcha is understanding and reviewing the existing access of the people that are part of the divestiture because you will now need to consider them outsiders. All of your standard off-boarding processes will apply here such as terminating accesses to make sure someone doesn’t retain access to a system they are no longer authorized to access (like HR, Finance, etc.).

Things can get complicated if parts of the business are divesting, but not fully. Some examples of this are when the business divests a smaller part, but allows the smaller part to co-locate in their existing facilities. This may complicate physical security requirements such as how to schedule or access common areas, how to schedule conference rooms, how to separate wifi and network access, etc. In the above example, the larger company may act like a service provider to the divested part of the business, but there still needs to be effective security controls in place between the two parts.

Personnel Security

I touched on this a bit already, but personnel security is something to consider when performing M&A or divestitures. With M&A the biggest issue will be how to smash the two IAM systems and HR systems together without punching huge holes in your network. Typically what happens is the two parts operate separately for a while and then consolidate to a single system and the employees of the acquired business get new accounts and access.

For divestitures, particularly if they don’t result in a clean split, you will need to focus heavily on access control and insider threats. Think about how you will separate access to things like source code, financial systems, HR systems, etc. If the smaller company has physical access to your space then you need to build in proper physical and logical controls to limit what each business can do, particularly for confidentiality and competitive reasons.

What’s an example of where this can go wrong? Let’s say business A is going to divest a small part of its business (business B). The complete divestiture is going to take a while to finalize so company A agrees to allow company B to continue to access their existing office space, including conference rooms. However, the legal team didn’t realize the conference rooms are tied to company A’s SSO and calendaring system so company B has no way to schedule the conference rooms without retaining access to company A’s IAM system creating a major security risk. Whoops!

The biggest gotcha is understanding and reviewing the existing access of the people that are part of the divestiture because you will now need to consider them outsiders.

Contracts

Contracts may not seem like a typical security issue, but they should be part of your review, particularly when performing M&A. Why? You are acquiring a business that is worth something and that business will have existing contracts with customers. The contractual terms with those customers may not match the contractual terms of the acquiring company, which can cause a risk if there is a significant difference in contract terms. Smaller companies are more agile, but they also usually have less negotiating power compared to large companies and as a result are more likely to agree to non-standard contract terms. What are some terms you need to think about?

  • Vulnerability Remediation Times – How quickly did the new company promise to fix vulnerabilities for their customers?
  • Incident & Breach Disclosure Time Frames – How quickly did the new company promise to notify customers of a breach or incident? I have seen very small time frames suggested in contracts, which are impossible to meet, so I definitely recommend reviewing these.
  • Disclosure of Security Postures – Does the new company have contractual terms promising to provide SBOMs or other security posture assessments to their customers on a regular basis?
  • Compliance Requirements – Has the new company agreed to be contractually obligated to maintain compliance certifications such as PCI-DSS, SOC 2, ISO27001, etc.
  • Penetration Testing & Audits – Has the new company contractually agreed to have their products or services penetration tested or have their security program audited? Have they agreed to provide these reports to their customers on a regular basis?
  • Privacy & Data Governance Terms – Is the new company required to comply with privacy regulations such as allowing customers have their data deleted, or mandating certain data governance requirements like DLP, encryption, data deletion, etc?
  • BCP/DR and SLAs – Are there contractual uptime SLAs or response times and does the existing BCP/DR plan support these SLAs?

My advice is to set a timeline post acquisition to review and standardize all of your contracts to a single set of standard clauses covering the above topics. This is usually part of a security addendum that the legal team can help you create. The biggest challenge with contracts will be to “re-paper” all of your customers to hopefully get them on the same standardized contract terms so your security program doesn’t have a bunch of different requirements they have to try to meet.

Accuracy Of M&A’s

One of the biggest risk of performing M&A’s is trying to get an accurate picture of the existing security posture of the company being acquired. Why is this so difficult? The company being acquired is trying to look as good as possible so they get top dollar. They can’t hide things, but they aren’t going to tell you where all the skeletons are buried either. The acquiring company usually doesn’t get a full picture of the existing security posture until after the deal is done and you start trying to integrate the two parts of the business. If you have a chance to interview the existing security team before the M&A closes definitely ask to see their latest audit reports, compliance certifications, penetration testing reports, etc. Consider working with legal to set conditions for how old these reports can be (e.g. no older than 6 months) to hopefully give you a more accurate picture or require the acquired company to update them before the deal closes. Interview key members of the staff to ask how processes work, what are their biggest pain points, etc. Consider hiring an outside company to perform an assessment, or you can even consider talking to one of their largest customers to get their external view point (if possible).

Wrapping Up

M&A and divestitures can be exiting and stressful at the same time. It is important for the security team to be integrated into both processes and to have documented steps to make sure risks are being assessed and addressed. I’ve listed a few key focus areas above, but most importantly standardizing your M&A security review can help avoid “buyers remorse” or creating unnecessary risk to the acquiring business. Finally, having a documented divestiture process and reviewing the divestiture with legal can help avoid security risks after the fact.

Should There Be A Professional CISO Certification and Organization?

I’ve been thinking a lot about the CISO role and how it is rapidly maturing from a technology and compliance role to a more generalized business executive role that specializes in security and risk. The primary catalyst for this evolution is the recent release of the SEC rules requiring companies to report material incidents on their 8K forms. It also requires companies to disclose their process for governing security issues (via committees or other processes) and their process for determining materiality (via their annual 10k filing). All of this is having a similar effect on the CISO role that Sarbanes-Oxley had on the CEO and CFO role after it was passed in 2002. The end result is public companies are now being expected to demonstrate investment and expertise in governing security issues, which is elevating the CISO role to become a true executive officer and is ushering the role into the board room.

Why Did The SEC Establish The New Requirements?

Security reporting and disclosures by public companies has been lacking. There has been zero incentive or accountability for companies to report these events other than via lawsuits, stock price corrections or brand and reputation impact These disclosures often happen as a result of a news report published months or years after the actual incident. The company then issues a generic statement downplaying the event and emphasizing how serious they take security. The SEC has determined this pattern of behavior is insufficient for investors to accurately make decisions about the health of the company.

Why Do Professional Certifications Exist?

Professional certifications exist for a number of reasons. Doctors, accountants. professional engineers and lawyers all must demonstrate a minimum level of knowledge to get licensed in their chosen profession. They must also agree to conduct themselves according to a specific code of conduct. This allows the practitioners to wield specific credentials demonstrating proficiency and credibility in that field. Displaying professional credentials attests these professionals bear the responsibility to protect life, prevent fraud or protect assets.

Additionally, professional credentials afford the practitioners a number of benefits such as knowledge sharing, continual career development, job placement and act as a back stop if someone’s conduct is called into question. Certifying organizations can testify on someone’s behalf if they believe they have upheld the requirements of the profession, or they can self regulate and strip someone of their credentials for fraud or gross negligence.

A short list of fields with professional certifications are as follows:

  • Lawyers – Bar
  • Doctors – Medical license, National Board of Medical Examiners (NBME), State level licenses, American Board of Medical Specialities (ABMS)
  • Accountants – Financial Accounting Standards Board (FASB), Government Accounting Standards Board (GASB), Generally Accepted Accounting Principles (GAAP), Certified Public Accountant (CPA)
  • Engineers – Certified Professional Engineer (CPE)
  • Privacy Professionals – International Association of Privacy Professionals (IAPP)

Existing Security Certifications And Organization Are Lacking

There are already a number of certifications security professionals can choose from on their path to becoming a CISO. A short list of common certifications listed on CISO job postings or LinkedIn profiles is as follows:

  • C|CISO
  • CISSP
  • CISM
  • CISA
  • CRISC

Of these certifications, only the C|CISO certification comes close to offering a specific certification for CISOs. The rest serve either as generalized security certifications or specific offshoots of the security profession. These certifications are often bundled together by professionals to demonstrate breadth of knowledge in the security field.

While existing certifications are good, they are all lacking in what is needed for someone to serve as a CISO at a publicly traded company. They are more generalized about how to serve as a CISO at any company (small to large), but publicly traded companies have specific requirements and demands. Specifically, most of the certifications above are extremely heavy on a breadth of technical aspects and popular industry frameworks. Some of them do cover how to create and manage a security program. Some even cover basic board level conversations (although these are usually technical discussions, which are unrealistic). Where I find these certifications lacking is as follows:

  • Realistic board level conversations about risk and tradeoffs including building effective presentations
  • Board and legal conversations about materiality for security incidents
  • Common board committees and what to expect as a CISO serving on a board level committee for your company
  • Testifying or providing legal evidence post incident
  • Legal conversations about how to best notify customers of breaches including drafting communications
  • Legal conversations with security researchers and navigating vulnerability disclosures
  • How to establish and manage a bug bounty program
  • Navigating conversations with law enforcement or national security issues
  • How to effectively change or strengthen security culture
  • How to have conversations with other C-Suite executives about security
  • Navigating customer and industry requests for disclosure of security program information
  • Managing the budget / P&L for a security function including tooling, licenses, services, travel, expenses, equipment, certifications, etc.
  • Common security team structures and how to design a security org that add maximum value for the business
  • Personnel management, skillsets expected for different roles, matching training and certifications to job function, etc.
  • Negotiating with vendors and cyber insurance companies
  • Contract review and negotiation with customers (including common security and privacy clauses)
  • Creating RFPs, RFIs and RFQs
  • Talking to customers about security at your company or hot button security issues
  • Establishing requirements, conducting trade-off analyses and performing build vs buy analysis
  • How to effectively network with peers
  • Industry resources such as ISACs, Infraguard, etc.
  • Top recruiting agencies for placing CISOs at publicly traded companies
  • Career development post operational CISO (boards, consulting, etc.)
  • Properly documenting your security program
  • How to navigate achieving common compliance certifications such as SOC1, SOC2, FedRAMP, ISO27001, HIPAA, PCI-DSS. Typical costs, consulting companies that can help with these processes and what to expect during the process.
  • When to outsource your security program to an MSP
  • When to bring in an outside consulting or incident response firm
  • Successfully passing an external audit
  • Negotiating for a job including severance, D&O liability, assessing the role, etc.
  • Differences in the CISO role depending on who it reports to (General Counsel, CTO, CIO, CEO, CFO)
  • How to navigate common security related political and moral hazards at public companies

As you can see, there is a big difference between what certifications offer and the real demands of a public company CISO. Additionally, there are a number of professional security organizations such as the Information Systems Security Certification Consortium (ISC2), Information Systems Audit and Control Association (ISACA) and The Council of E-Commerce Consultants (EC-Council). Each has their own certification track, terminology and code of conduct. Each is good in their own right, but there is still a lack of a single certifying body for public company CISOs similar to a CPA. Arguably, ISACA comes closest to being an international organization that can back CISOs, but they lack a CISO specific certification covering the majority of the topics above.

While existing certifications are good, they are all lacking in what is needed to prepare someone to serve as a CISO at a publicly traded company.

Why There Should Be A Professional CISO Certification

The SEC requirements are forcing public companies to govern security to the same standard forced by Sarbanes-Oxley 20 years ago. The SEC considers security to be a material concern to investors and public companies need to treat the issue accordingly. As a result CISOs are getting elevated to the board room and CISOs need to be prepared to navigate the issues they will encounter while serving at a public company.

The advantages of a professional CISO certification and accompanying organization are as follows:

  • Standard of ethics and conduct – CISOs face a difficult job and often walk into roles that aren’t properly supported or properly funded. Yet, CISOs are asked to bear the responsibility and accountability for the security health of the organization. A standard of ethics and conduct, similar to a CPA, will backstop the authority of the CISO and serve as guidelines for how to navigate common issues at publicly traded companies.
  • Standard credential for publicly traded companies – Large companies face a difficult job sorting through the credentials and titles of job applicants. Most public companies hire executive recruiting firms to help navigate the sea of candidates to find ones that are truly qualified for the role. However, a single professional CISO certification would distinguish individuals who have met the standard to be a CISO at a publicly traded company and distinguish these credential holders from other individuals with discretionary CISO titles.
  • Shelter the role from (some) liability – One advantage of a professional certification like the ones for doctors, engineers, lawyers and public accountants is it provides a standard of conduct. These professionals can fall back on this standard of conduct if their professionalism is called into question and they can even have the certifying organization offer testimony on their behalf. As CISO take on more liability, a professional CISO organization can be useful to help support CISOs, testify on their behalf, offer recommendations for liability insurance policies or even provide low cost liability insurance through the organization. They can even help review employment contract terms to evaluate liability policies, severance, legal coverage, etc.
  • Board Level Expertise – One of the primary roles of public company CISOs is to present to the board and help the company navigate regulatory and compliance requirements such as SEC filings, breach notifications, etc. A professional CISO certification offer individuals this experience and it can give them the confidence to speak to the board on how to navigate topics of risk. By certifying individuals are qualified to operate in the board room the board will gain another voice to balance the other C-Suite executives who aren’t grounded in technology and security issues.
  • Consulting and auditing – One final advantage of a professional CISO certification is for the “big 4” consulting firms or other agencies who are contracted by investment companies to audit and certify the filings and reports of public companies. In this case, a certified CISO can represent shareholders and investors for the accuracy of security filings around governance processes, representation in board committees, recommendations for appropriate investment in security governance and generally offering advice on industry best practices for security governance at publicly traded companies.

Wrapping Up

I’m bullish on the CISO role long term because I think it is the ultimate C-Suite executive. Public company CISOs touch all aspects of the business, they need to have strong technical chops, need to understand business topics and need to have the political chops to build alliances and navigate big company politics. Existing security certifications are good, but none of them offer a comprehensive breadth of topics to prepare individuals to become a CISO at a publicly traded company. As CISOs establish their role and credibility in the board room, it will become critical for these individuals to have credentials that back their experience, offer support and can elevate the CISO role on par with other C-Level execs, similar to what Sarbanes-Oxley did for CFOs after 2002.

Are We Peak CISO?

Let’s be honest…the CISO role is weird right now. It is going through a transformative phase and the industry is at an inflection point similar to what other C-Level roles (like the CFO) have gone through in the past. What makes the role weird? The CISO community and any company that has a CISO is facing unprecedented regulatory pressure, the economy and interest rates have people on edge, layoffs in the tech sector have shaken employee confidence (to the applause of investors) and technology innovation via AI is causing additional disruption and risk across all sectors.

In additional to these external pressures the past few years have seen the proliferation of CISO title sprawl and confusion from companies about how to best employ and utilize a CISO (hint, we aren’t your scapegoats). Despite all of this turmoil, change is also a time for opportunity and there are a few things I think will help clarify and mature the CISO role.

CISO Title Sprawl

I’ve been tracking job titles and job postings on LinkedIn for the past year or so and I’ve noticed a phenomenon I’ll call title sprawl. A quick search for titles shows there are vCISOs, Advisory CISOs, Fractional CISOs, CISOs In Residence and Field CISOs. On top of this, add in Chief Security Officers, Chief Trust Officers and Heads of Security. Do we need all of these titles? Maybe, but I think this title sprawl is more indicative of three things 1) People with CISO titles are in high demand and people want to retain the title once they get it and 2) Companies are still uncertain about how to title and employ someone to lead their security function. 3) Title sprawl is a result of the political power struggle occurring between the CISO role and other C-Level roles (more on that below).

From the titles above there are really only four functions for a current or former CISO – board member (in some capacity), executive management (officer of the company), consultant and sales. There is similar title sprawl and variance with CTO titles, but not to the extent of the CISO title (yet). Time will tell if other C-Level roles start to follow suit, but for now, let’s break down the functional CISO role buckets.

Board Member – These are current or former CISOs who sit on a board either as a technical advisor, business advisor or some combination thereof.

Executive Management – Individuals employed by a company to lead the information security program. May also manage other parts of IT such as identity, privacy, data, etc. Titles may be CISO, CSO, CISO in Residence (for Venture Capital), Chief Trust Officer and Head of Security.

Consultant – These are individuals who are providing their expertise as a current or former CISO to other companies to help them establish, transition or manage a security program. Often the companies employing these individuals claim they can’t afford a full time CISO, but they seem to be able to afford other full time C-Suite titles (hmm…)? Titles may include Virtual CISO (vCISO), Fractional CISO, CISO in Residence and Consulting CISO. (CISO in Residence again because they can “consult” to their VC holding companies about the state of their security programs).

Sales – These are people who are experts in the field of security, may hold one or more certifications and may be past CISOs. Their job is to help the company they work for drive sales. Typically the title they use is Field CISO or Advisory CISO.

Standardize The Reporting Structure

Moving on from title sprawl, companies are also confused about where the CISO title should sit. Some companies advertise it as a Director level role reporting into the VP of some function. Other’s title it as a VP level role reporting into a Senior VP or some other executive. Still other companies have the CISO reporting to the CEO, CIO, CTO or General Counsel. It is even possible this person is an individual contributor. Companies are clearly confused about whether the CISO is a technologist, regulatory compliance specialist or true C-Suite executive. While reporting structure may be a direct reflection on company culture, it is also a public example of the battle for equivalency that is playing out between the CISO and other C-Level roles. Often, CISOs are hired by other C-Levels (not the CEO) and until it becomes more common for CISOs to report to the CEO as an accepted peer to other C-Levels, this confusion and variance will persist. That being said, if you are considering a CISO title and the company isn’t willing to add you to the D&O liability policy then you may be better off taking a lower level title to eliminate personal risk.

Bolster Security Management Certifications

Security certifications from popular organizations talk a lot about regulations, risk and different security concepts (technical or not), but few, if any, offer a comprehensive certification on what it truly takes to be a CISO. Any CISO level certification should include potential career paths that lead to the CISO role, career paths post CISO role, difference in the CISO role based on company size, exposure to business topics in addition to security topics, SEC reporting, interfacing with law enforcement and lastly discussion of how to maximize success based on where the role sits – e.g. reporting to the CEO, CTO or CIO and how that may change your lens as a CISO. This begs the question if there should be a true professional level CISO certification similar to a professional engineer, accountant or lawyer, but let’s save that discussion for a future blog post.

Embrace Increased Regulation

Given the recent increase in regulation, particularly from the SEC, bolstering CISO certifications to include more business acumen may soon be table stakes instead of a nice to have. Recent regulations forcing companies to disclose material cybersecurity events in their 8k filings are starting to accelerate the maturity of the CISO role at publicly traded companies. Companies can no longer fail to invest in security or report breaches (unless they want steep penalties). In particular, this is forcing the CISO role into the board room or at least on par with other C-Level roles because they have to help these companies navigate the decision to report material events in their filings. Existing and future CISOs can embrace this increase in regulation to backstop their authority at companies who are struggling to fully embrace the CISO role as a C-Level executive. While it may not elevate the current role with a promotion, it should at least open the door to the board room and provide a seat at the table for discussion.

While CISO reporting structure may be a direct reflection on company culture, it is also a public example of the battle for equivalency that is playing out between the CISO and other C-Level roles.

The last point I’ll make about regulation is – while the SEC watered down the requirements for cybersecurity expertise on boards, I predict this expertise will still be required and in demand as companies start to navigate the new SEC reporting requirements. In particular, companies may be penalized and eventually required to demonstrate cybersecurity board expertise (via experience or certifications) if they are found to have a material security breach and can’t demonstrate appropriate security governance at the board level.

What’s The End Result?

It is clear the security industry and the CISO role are in a state of confusion as a result of the tight job market, uncertain economy, increased regulation and pace of technology innovation. The net effect of title sprawl and the struggle for equivalency is – it confuses customers, investors, partners, recruiters and job candidates. Title sprawl artificially increases competition for jobs and causes a wide variance in how the CISO role is employed. However, I think this state of confusion is a good thing because it is forcing conversations and causing people to stop and think. The CISO role is the newest member of the C-Suite and it is growing up and trading in the hoodie for a collared shirt. We are starting to claim our seat at the board level and are able to hold our own or make other C-Level roles redundant. As the CISO role evolves from a “nice to have” to a “must have” in the C-Suite, we will see this confusion fade away and the CISO role will truly reach its peak.

What’s The Relationship Between Security Governance and Organizational Maturity?

Organizational and security governance is touted as a key component of any successful security program. However, I’ve been thinking about governance lately and how it relates to the overall maturity of an organization. This has prompted some questions such as: what happens if you have too much governance? and What’s the relationship between security governance and organizational maturity?

What Is Governance?

First, let’s talk about what governance is.

Governance is the process by which an organization defines, implements and controls the business.

Let’s unpack what this means for a security organization. The process of defining security for the business is done through policies, standards and guidelines. Security policies are requirements the business must meet based on laws, regulations or best practices adopted by the business. These policies align to business objectives. Implementation is done through security controls that are put in place to meet a specific policy or to manage a risk. Lastly, controlling the business is done via audits and compliance checks. The security org follows up on how well the business is following policies, implementing controls and managing risk. Control can also include enforcement, which can involve gating processes, such as requiring approval for business critical and high risk activities, or recommending additional security requirements for the business to manage a risk.

Why Do We Need Governance At All?

In an ideal world we wouldn’t. Imagine a business that is created entirely of clones of yourself. There would be implicit and explicit trust between you and your other selves to do what is best for the business. Communication would be simple and you would already be aligned. In this case you don’t need a lot (or any) governance because you can trust yourself to do the things. However, unless you are Michael Keaton in Multiplicity, this just isn’t a reality.

Governance achieves a few things for a business. First, it communicates what is required of its employees and aligns those employees to common objectives. Second, it helps employees prioritize activities. None of this would be needed if human’s weren’t so complex with diverse backgrounds, experiences, perspectives, education, etc. In an ideal world we wouldn’t need any governance at all. The reality is, we do need governance, but it needs to be balanced so it doesn’t unnecessarily impede the business.

How Does This Relate To Organizational Maturity?

Organizational maturity refers to how your employees are able to execute their tasks to achieve the objectives of the business. This relates to things like the quality of code, how quickly teams resolve operational issues or how efficiently they perform a series of tasks. It can be loosely thought of as efficiency, but I actually think it combines efficiency with professionalism and integrity. Maturity is knowing what good is and being able to execute efficiently to get there. There is a fantastic book about this topic called Accelerate: The Science of Lean Software and DevOps: Building High Performing Technology Organizations by Nicole Forsgren PhD.

Which brings us to the relationship of governance and maturity…

There is an inverse relationship between organizational maturity and organizational governance. In simple terms:

The less mature an organization, the more governance is needed.

For example, if your organization struggles to apply patches in a timely manner, continually introduces new code vulnerabilities into production or repeatedly demonstrates behavior that places the business at risk, then your organizational maturity is low. When organizational maturity is low, the business needs to put processes and controls in place to align employees and direct behavior to achieve the desired outcomes. In the examples above, increased governance is an attempt to manage risk because your employees are behaving in a way that lacks maturity and is placing the business at risk.

What causes low organizational maturity?

Organizational maturity is a reflection of employee behavior, skillset, knowledge, education and alignment. In other words, organizational maturity is a reflection of your organizational culture. In practical terms your employees may simply not know how to do something. They may not have experience with working for your type of business or in the industry you operate in. Perhaps they had a really bad boss at a past job and learned bad behavior. Whatever the reason, low organizational maturity is linked to lots of sub-optimal outcomes in business.

How To Improve Organizational Maturity?

If governance and maturity are inversely linked, the question becomes how can we increase organizational maturity so we need less governance? There are a lot of ways to increase organizational maturity. One that is fairly obvious is to start with a mature organization and maintain it over time. However, this is easier said than done and is why some organizations are fanatical about culture. This relates to everything from hiring to talent management and requires strong leadership at all levels of the company.

“The less mature an organization,
the more governance is needed.”

Other ways to improve organizational maturity are through training and education. This is why security awareness and training programs are so critical to a successful security program. Security awareness and training programs are literally attempting to improve organizational maturity through education.

One last way to improve maturity is via process. The security organization can establish a new process that all teams must follow. As teams go through this process you can educate them and reward teams that exhibit the ideal behavior by relaxing the process for them. You can also help teams educate themselves by publishing the requirements and making the process transparent. The challenge with imposing a new process is having the discipline to modify or remove the process when needed, which comes back to governance.

What’s the right level of governance?

The optimal level of governance is going to be based on your organizational maturity and desired business outcomes. In order to determine if you have too much or too little governance you need to measure organizational maturity and the effectiveness of existing organizational governance. There are industry standard processes for measuring organizational maturity, like the Capability Maturity Model Integration (CMMI) and Six Sigma, or you can create your own metrics. Some ways to measure governance effectiveness are:

  • Ask For Feedback On Security Processes – Are the processes effective? Do teams view them as an impediment or are they viewed favorably? Are the processes easy to navigate and objective or are they opaque and subjective?
  • Measure Effectiveness Of Security Controls – Are your security controls effective? If you ask a team to do work to implement a security control you should have clear metrics that determine if that control is effective. If you implement a control, but that control hasn’t changed the outcome, then the control is ineffective. This can indicate your governance is ineffective or your organizational maturity needs to improve.
  • Assess and Update Policy – Security policies should be living documents. They shouldn’t be set in stone. Security policies need to map back to laws and regulations they support and the business requirements needed to be successful. Laws, regulations and business requirements all change over time and so should your security policies. By having up to date and relevant security policies you can ensure your organizational governance matches the maturity of the business.

What Are Typical Scenarios For Governance And Maturity?

There are four scenarios related to governance and maturity:

A mature organization with too much governance – your organization is mature, but you are overly controlling with process and requirements. The net effect will be to slow down and impede the business unnecessarily. You are effectively lowering the organizational maturity due to too much governance.

An immature organization with too little governance – this is a recipe for disaster. If your organization is immature and you fail to govern the organization you will open the business up to unnecessary risk. You will get out maneuvered by your competitors, you will miss opportunities, you will fail to comply with laws and regulations and generally will have a lot of activity without any result. Your employees will lack coordination and as a result your business will suffer.

A mature organization with too little governance – This isn’t a bad scenario to be in. A mature organization implies they are doing the right things and don’t need a lot of guidance. A laissez faire attitude may be the right thing to allow employees flexibility and freedom, but it does come with inherent risk of not being compliant with laws and regulations. It may also mean there is duplication of effort or multiple ways of doing things, which could be optimized.

Governance and maturity are balanced – obviously this is the ideal scenario where your organizational governance is balanced to the level of maturity of the organization. Easy to think about in practice, difficult to achieve in reality.

Wrapping Up

Organizational governance and maturity are inversely related and need to be balanced in order for the business to operate effectively. There are ways to measure organizational maturity and governance effectiveness and by having a continual feedback loop you can optimally align both for success.

Are Traditional IT Roles Still Relevant In Today’s Modern Security Org?

As more and more businesses shift to the cloud and micro-services, the scope of responsibility for security and operations gets pushed up the stack. As a result of this scope compression, teams no longer need to worry about maintaining physical infrastructure like deploying servers, provisioning storage systems or managing network devices. As this scope falls off, the question becomes – are traditional IT roles still relevant in today’s modern security org?

Cloud Service Models

First, let’s talk about cloud service models most companies will consume because this is going to determine what roles you will need within your security organization. This post is also assuming you are not working at a hyper-scale cloud organization like AWS, Azure, Google Cloud or Oracle because those companies still deploy hardware as part of the services they consume internally and provide to their customers.

Infrastructure as a Service (IaaS)

Infrastructure as a Service (IaaS) is what you typically think of when you consume resources from a Cloud Service Provider (CSP). In IaaS, the CSP provides and manages the underlying infrastructure of network, storage and compute. The customer is responsible for managing how they consume these resources and any application that are built on top of the underlying IaaS.

Platform as a Service (PaaS)

In Platform as a Service (PaaS), the cloud service provider manages the underlying infrastructure and provides a platform for customers to develop applications. All the customer needs to do is write and deploy an application onto the platform.

Software as a Service (SaaS)

With Software as a Service (SaaS) customers consume software provided by the cloud service provider. All the customer needs to worry about is bringing their own data or figuring out how to apply the SaaS to their business.

IaaS, PaaS & SaaS Cloud Service Provider Logical Model

As you can see from the above model, organizations that adopt cloud services will only have to manage security at certain layers in the stack (there is some nuance to this, but let’s keep it simple for now).

What Are Some Traditional IT Roles?

There are a variety of traditional information technology (IT) roles that will exist when an organization manages their own hardware, network connections and data centers. Some or all of these roles will no longer apply as companies shift to the cloud. Here is a short list of those roles:

  • Hardware Engineer – Server and hardware selection, provisioning, maintenance and management (racking and stacking)
  • Data Center Engineer – Experience designing and managing data centers and physical facilities (heating, cooling, cabling, power)
  • Virtualization Administrator – Experience with hypervisors and virtualization technologies*
  • Storage Engineer – Experience designing, deploying and provisioning physical storage
  • Network Engineer – Experience with a variety of network technologies at OSI layer 2 and layer 3 such as BGP, OSPF, routing and switching

*May still be needed if organizations choose to deploy virtualization technologies on top of IaaS

Who Performs Traditional IT Roles In The Cloud?

Why don’t organizations need these traditional IT roles anymore? This is because of the shared service model that exists in the cloud. As a customer of a cloud service provider you are paying that CSP to make it easy for you to consume these resources. As a result you don’t have to worry about the capital expenditure of purchasing hardware or the financial accounting jujitsu needed to amortize or depreciate those assets.

In a shared service model the CSP is responsible for maintaining everything in the stack for the model you are consuming. For example, in the IaaS model, the CSP will provide you with the network, storage and compute resources you have requested. Behind the scenes they will make sure all these things are up to date, patched, properly cooled, properly powered, accessible and reliable. As a CSP IaaS customer, you are responsible for maintaining anything you deploy into the cloud. This means you need to maintain and update the OS, platform, services and applications that you install or create on top of IaaS as part of your business model.

Everything Is Code

One advantage of moving to the cloud is everything becomes “code”. In an IaaS model this means requesting storage, networking, compute, deploying the OS and building your application are all code. The end result of everything is code means you no longer need dedicated roles to provision or configure the underlying IaaS. Now, single teams of developers can provision infrastructure and deploy applications on demand. This skillset shift resulted in an organizational shift that spawned the terms developer operations (DevOps) and continuous integration / continuous delivery (CI/CD). Now you have whole teams deploying and operating in a continuous model.

Shift From Dedicated Roles To Breadth Of Skills

Ok, but don’t we still need traditional IT skills in security? Yes, yes you do. You need the skills, but not a dedicated role.

Imagine a model where everyone at your company works remotely from home and your business model is cloud native, using PaaS to deploy your custom application. As the CISO of this organization, what roles do you need in your security team?

From a business standpoint, you still need to worry about data and how it flows, you need to worry about how your applications are used and can be abused, but your team will primarily be focused on making sure the code your business uses to deploy resources and applications in the cloud is secure. You also need to make sure your business is following appropriate laws and regulations. However, you will no longer need dedicated people managing firewalls, routers or hardening servers.

What you will need is people with an understanding of technologies like identity, networking, storage and operating systems. These skills will be necessary so your security team can validate resources are being consumed securely. You will also need a lot of people who understand application security and you will need compliance folks to make sure the services you are consuming are following best practices (like SOC 2 and SOC 3 reports).

What Do You Recommend For People Who Want To Get Into Security Or Are Deciding On A Career Path?

I want to wrap up this post by talking about skills I think people need to get into security. Security is a wonderful field because there are so many different specialization areas. Anyone with enough time and motivation can learn about the different areas of security. In fact, the U.S. Government is kind enough to publish a ton of frameworks and documents talking about all aspects of security if you have the time and motivation to read them. That being said, if I was just starting out in security I would advise people to first pick something that interests them.

  • Are you motivated by building things? Learn how to be a security engineer or application security engineer. Learn how to script, write code and be familiar with a variety of technologies.
  • Are you motivated by breaking things? Learn how to be a penetration tester, threat hunter or offensive security engineer.
  • Do you like legal topics, regulations and following the rules? Look into becoming an auditor or compliance specialist.
  • Do you like detective work, investigating problems and periodic excitement? Learn how to be an incident response or security operations analyst.

Ask Questions For Understanding

The above questions and recommendations are just the tip of the iceberg for security. My biggest piece of advice is once you find an area that interests you start asking a lot of questions. Don’t take it for granted that your CSP magically provides you with whatever resources you ask for. Figure out how that works. Don’t blindly accept a new regulation. Dissect it and understand the motivation behind it. Don’t blindly follow an incident response playbook. Understand why the steps exist and make suggestions to improve it. If a new vulnerability is released that impacts your product, understand how and why it is vulnerable. The point is, as a security professional the more understanding you have of why things exist, how they work and what options you have for managing them, the more skills you will add to your resume and the more successful you will be in your career, especially as your security org collapses roles as a result of moving to the cloud.

The Dichotomy Of Security

If you have ever read Extreme Ownership or The Dichotomy of Leadership by Jocko Willink, then you will be familiar with the concept of dichotomy and how opposing forces of a skill set can compliment each other. Mastering both sides can allow flexibility and increase the effectiveness of that skill set when dynamically applied to a given situation. This is true in the security space, where fundamental opposing forces need to be balanced in order to manage risk and achieve success. Let’s take a look at a few examples.

Security Extremes

The easiest example of the dichotomy of security is to look at the extremes. Security professionals jokingly say the most secure company is one that is not connected to the internet. While this may be true, it will also prevent the company from conducting business effectively and so the company will cease to exist and security will no longer be needed.

On the other end of the spectrum there is the extreme of a business that has zero security and so there are no impediments to conducting business. While this may sound great to some, the reality is the company will be unable to effectively conduct business because of the real threats that exist on the internet. In the situation the company will also cease to exist because they will be hacked into oblivion.

It is obvious there is a dichotomy between no security and no connectivity and these forces need to be appropriately balanced for a security program to be effective, while allowing the business to operate.

Manual vs Automated Security

Another example of dichotomy is between manual security tasks and automation. While every CISO I know is striving to increase automation of security tasks, the reality is humans are still going to be needed in any security program for the foreseeable future.

Manual tasks are ideal for situations where humans need to demonstrate creativity, intuition or make complex decisions based on subtle context. Security functions like penetration testing, threat hunting, red teaming and offensive security require high amounts of skill and experience that automation, like AI, hasn’t been able to replicate. Additionally, soft skills such as reporting to the board, shifting culture, building alliances and making prioritization decisions are all extremely complex and unlikely candidates for automation. However, while manual activities benefit activities that require a high degree of creativity, they are inherently slow and can impede the normal flow of business.

Recently, the advances in automation and artificial intelligence have exponentially increased their usefulness. Automation is extremely useful for offloading repeatable tasks that lend themselves to being programmatically defined. For example, attack simulation products have made huge strides in offloading repetitive tasks of reconnaissance, enumeration, vulnerability assessment and remedial exploitation. We are seeing additional advances in automation related to incident response where events can be correlated and specific activities in an IR playbook can be completed to offload analysts and help focus their attention. AI has also helped to offload lower level operational activities like call centers and help desk inquiries.

While automation may accelerate parts of the business and offload humans from repeatable tasks, it does introduce complexity, which can be difficult to troubleshoot or can cause outright failures. Automation is also rigid because it is only as good as the parameters of the process it is following. This means it can’t think outside of the box or demonstrate creativity. There is also the risk of introducing bias into your processes if your underlying model is flawed.

As you can see manual security processes and automated security processes are opposing forces that need to be balanced based on the skill of your security team and the needs of the business.

The Human Problem

The last dichotomy I want to discuss is the human problem in security. Humans are necessary because of their creativity, diversity and capacity for adapting to an infinite number of situations. However, the flexibility in human nature also presents one of the fundamental security problems – how to you protect against human nature?

The reality is humans are flawed, but in a good way. Threat actors can try to take advantage of these flaws, whether they are logical (like firewall rules) or physical (like human psychology). Humans are essential to every aspect of a business and so we have to figure out how to protect them. The most difficult balance in security is developing a program that is comprehensive enough to protect against human nature without stifling it.

The Security Ideal

The ideal security program will recognize the dichotomy of the security challenges it faces and balance them accordingly. The ideal security program balances security with flexibility. We are seeing this balance manifest in mature security programs via concepts like security guard rails and the paved path. The paved path and guard rails attempt to allow a certain amount of latitude for acceptable behavior, while being rigid enough to protect users and the business accordingly.

Application In Other Domains

The concept of dichotomy is universal across any domain. In fact, this is an area of extensive research in disciplines like mathematics, computer science, military strategy, and economics. Specifically, in the space of network and graph theory there is a concept call max flow, min cut. These are counter principles that are opposite, yet complimentary. If you think of any network (road, supply chain, computer network, etc.) the point of maximum flow across that network is also the point where maximum disruption (minimum cut) can occur. From a military or security stand point you will want to protect the max flow/min cut, but from an attacker stand point, the max flow / min cut, is the area that will require the least amount of effort for maximum damage. Pretty neat!

Wrapping Up

An effective security program will balance the needs of security with the needs business with the ultimate goal of effectively managing risk. A critical skill for any security practitioner is to be flexible and adaptive. Specifically, by recognizing that security issues have two sides to them, security practitioners can demonstrate empathy towards the business and find an appropriate balance that can protect without impeding the business.

Defining Your Security Front Door

A key skill for any security program is to partner with and enable the business to be successful. CISOs need to ensure their security teams are approachable, reasonable and most importantly balancing the needs of the business against potential security risks. While security teams exist to help protect the business, they don’t own the business systems or processes and as a result need to adopt an advisory or consultative role with the rest of the business to ensure success.

With that in mind, the way the rest of the business finds and engages with the security team can create a good first impression or can set the tone for a difficult interaction. Think of a house that has great curb appeal – it feels inviting and gives the impression that the owners take good care of their property. The same concept exists for the security program, which I call the Security Front Door.

The Front Door Concept

The security front door defines how the rest of the business engages with and interacts with the security team. The front door can be a confluence page, slack channel with pinned information, or some place that is easily discoverable and accessible. Your security front door should clearly lay out information and resources so the rest of the business can either self serve or easily request and receive help when needed.

What Should Be In Your Front Door?

The front door for your security program should include ways to perform the most commonly requested actions from the security team. For example, you probably want really clear ways to request the following:

  • Report an incident
  • Request vulnerability remediation help
  • Request an exception
  • Request an architectural review
  • Dashboards
  • Discover documentation for policies and processes
  • Other – a general way to request help for anything else

The front door is not just a way to make a good first impression and enable the business, but when set up correctly it can actually offload the security team and help the business move faster.

Wrapping Up

The front door is a great way to engage with the business to help them move faster, find information and request assistance from the security team. When done correctly it can allow the rest of the business to self serve and can actually offload the security team by reducing the volume of requests that come in. Setting up the security front door may require a lot of up front work, but by understanding the rest of the business, their key pain points and most commonly requested security asks, you can design a front door that will be a win-win for everyone.

Annual Planning For CISOs

The beginning of the year is a popular time for making personal resolutions, which can focus on health, finance or love. While the beginning of the year is a popular time to set resolutions, really what we are talking about is setting goals to improve ourselves. I’m a huge proponent of setting personal goals for the year because it gives focus and purpose to your actions. The beginning of the year is also a great time to review the annual goals of your security program to set your focus and establish priorities. Annual planning has several objectives that CISOs need to consider and include in their process and I’ll cover them in the rest of this post.

Strategic Planning (Strat Planning)

Strategic, or “strat” planning as it is sometimes called, looks at where the business and your organization want to be over a long term time period. Something like 18 months to 5 years is typical in strat planning. The planning session should include discussion of the one or more of the following macro level business topics:

  • Market forces and opportunities
  • Industry trends
  • Regulatory and legal landscape
  • Competition
  • Customer sentiment, goals, etc.
  • Economic and financial environment
  • Geo-political climate
  • Technology trends and latest research

This discussion could be part of a SWOT analysis (Strengths, Weaknesses, Opportunities, Threats), but the goal is to understand where your business is and where you want it to go in the long term.

Align The Security Program

Once the business has a strategic plan, the CISO should conduct a similar planning exercise for where they want the security program to be. These are sometimes called “North Stars”, but they are essentially high level objectives over the long term that merge technology trends, regulatory requirements and security goals into long term objective. These won’t be very specific, but instead should act as guidance for where your team should focus and hopefully end up over the next few years.

Examples

An example of a strategic trend and security objective are as follows:

Trend: As companies shift from the datacenter to the cloud and bring your own device (BYOD), the concept of a traditional perimeter no longer makes sense.

Strategic Security Objective: Shift to a zero trust strategy where identity becomes the perimeter.

The goal is to choose big ticket objectives that will take multiple years to achieve, but will provide guidance to your org and the rest of the business about the direction your team is taking. Your strategic plan will inform the next section, which is your operational plan.

Operational Planning (Op Planning)

Operational planning is more tactical in nature and covers a shorter time period than strategic planning. Op planning usually follows either a fiscal or calendar year that way it aligns to performance reviews and budgeting cycles. In op planning the CISO will select the high level goals they want the security organization to complete that year. Usually op planning will include discussion and planning of the following:

  • Budget creation, forecasting and changes
  • Headcount planning
  • Technology investments (if any)
  • Top risks to focus on
  • Any audits or compliance certifications needed that year
  • Development of timing and roadmap for completing specific projects and tasks
  • Discussion of security controls and services
  • Skill gaps and training requirements

The point is to create a tactical plan for the year that will inform your team’s specific goals and objectives. These goals should be clear and measurable. I typically use an iterative approach to break my goals down to my directs and then they break their goals down to their teams and so on. This ensures alignment throughout the business.

Measuring and Adjusting

One important aspect of any plan is to continually measure progress and adjust if needed. Goals and objectives aren’t useful if the business has shifted and they are no longer relevant or have become un-obtainable.

Wrapping Up

Strategic and operational planning are important activities for every CISO. These plans define the long term vision for the security organization and break down that vision into tactical objectives that are accomplished throughout the year. This post discussed a high level overview of what goes into strategic and operational planning, but aligning security plans to business risk, mapping security controls, obtaining funding and reporting progress are all complex activities that every CISO needs to master.

Exploring The Advantages and Disadvantages of Centralized vs. Decentralized Teams

This blog post is part of the Compliance Corner Series developed in partnership with Milan Patel. This series includes a variety of discussion topics around the intersection of security and compliance. The series includes blog posts, live web streams (with Q&A) and podcasts.

What is more effective – A decentralized or centralized security and compliance team? What are the factors you need to consider, what are the pros and cons of each model, does company size matter, are they simply analogs of organizational maturity or should leaders consider one model over another model for their org?

  1. When leaders are creating or maturing their organization should they consider a centralized or decentralized organization structure?

Lee: If you have the opportunity to create or modify your organization I personally prefer a centralized organization structure. This is because it concentrates the roles, responsibilities and authority for security into a single function that can offer governance and all of the additional expertise expected of a security organization. The rest of the business knows where to go and who to talk to for all security issues. I have seen problems arise in both decentralized and heavily matrixed organizations because it confuses the roles and responsibilities of the function. Who is actually responsible for making security decisions if major parts of security are spread out across the organization? Sharing resources doesn’t really work very well because it is confusing for the individual team members and when sharing resources one side typically loses out to the other side. I have also seen shared resources get mis-used or repurposed for things other than security. This doesn’t mean the security team can’t place resources in different parts of the org, but they should report into and be owned by the security function. In my opinion whoever is responsible for the budget and the headcount truly controls that resource and decentralizing the budget and headcount causes problems.

Milan: Business leaders must first consider what role they want their compliance organizations to have. Will their compliance team actually offer governance, or just auditing? Are they going to cover corporate policies, or just audit frameworks that attest to customer reports? These are important scope questions to answer before setting up (or maturing) a compliance organization. It can drastically change how you fund and scope skills for the team, and whether a decentralized team will meet the overall risk management and corporate goals.

Investment size must also be considered, I get that question all the time, “How much should a business invest in compliance?”. I have seen everyone from flat personnel-project based funding, to actual percent of overall business operations spend. I focus on scope first, as then you can directly cost out what the deliverables/responsibilities are. Governance will drive a big factor of centralized or decentralized teams. Governance requires authority, charter, and appropriate level of independence to actually hold teams accountable. In a decentralized model, governance becomes much more difficult, as the fox ends up guarding the hen house.

  1. Does company size, organizational maturity or other factors influence the decision to have a centralized vs. decentralized organization?

Lee: Company size can definitely influence the initial decision to create a centralized or decentralized function. Smaller organizations or startups may not be able to justify the initial cost of a dedicated security leader and may lump this responsibility under the CIO, CTO or Chief Counsel. As a result the security function may initially grow as a decentralized function until the organization decides it is either time to offload the original leader or they realize they need more specific security leadership and it is time to build out a dedicated function.

Organizational maturity can also impact the decision. Immature organizations may struggle to effectively use decentralized resources and so the weaker the organizational culture the more a centralized security organization will make sense. However, in really large organizations it is common to see a hybrid approach which I like to call a federated model. In a federated model you have a centralized security organization that sets policy, governance, manages risk, makes decisions and has all the authority for anything security. Business units within the large company then staff specific security resources based on expertise for specific industries or to help navigate their specific security and regulatory requirements. This can be advantageous in terms of presenting a single view of overall risk, consolidating processes and leveraging economies of scale for purchases to get a better price for tools or contracts used for security across the organization.

Milan: Company size, and breath of products, can definitely influence the model. In smaller companies, there will likely be less resourcing (and complexity) to consider, which makes a centralized model more affordable and practical. You are not going to have much ability to fund a larger team (and wouldn’t likely need it), so a centralized model pretty much is the only option.

In larger companies, decentralization is used (and we’ll talk about advantages and disadvantages later), but the better model is hub and spoke. A strong central team, chartered with governance, but small “spoke” compliance teams that are the boots on the ground in the team. Small presence that can keep engineering on track, participate in design reviews, threat model reviews, and know enough to ensure that engineering teams and products are on the right track from the start. They also can drive best practices for that team, but they are based on the central team requirements, and can escalate to the central team (that ideally has a governance charter) to ensure adherence at the right senior level.

  1. What are the advantages and disadvantages of each model?

Lee: Centralized models offer consolidation of budget, resources, governance, responsibility and authority. It presents a single function that the rest of the business can go to for anything security related. Centralized models are typically more efficient because it avoids each group having to create and duplicate resourcing, tooling and processes. The one downside of a centralized model is if the security organization forgets that the rest of the business is their customer then it can become extremely difficult to interact with that group who effectively becomes a gatekeeper for business progress.

Decentralized models can offer some initial advantages when companies are extremely small. This is typical during startups or when you are operating in a mode where everyone is doing a lot of different jobs. However, this usually isn’t sustainable long term. I also find people who operate in this mode usually can’t scale to a larger organization where more governance is required. Decentralized models are also more prone to duplication of resources, technology and processes because there isn’t a single leader coordinating strategy and investment. Decentralized functions can also run into problems where the resources are misused or go “native” and stop performing the intended security role. Decentralized functions may end up with different levels of maturity across the different groups in the organization, which can make it difficult to obtain compliance certifications or to standardize processes and technology for a unified approach to security.

Milan: In general, a centralized structure offers the best overall coverage and governance. You can set consistent policies and practices across multiple organizations, which inherently will reduce risk as it’s easier to ensure consistency, and accuracy with one process vs many. You also can provide more controls to validate continuously that processes are working, plus attest much easier. Continuous compliance in a cloud environment is basically the norm now, but not all organizations, especially those with a decentralized model, can effectively ensure compliance of many regulations that come in and now must be enforced at the corporate level, and not just at the product level.

You also reduce cost, as having one set of compliance experts is cheaper, and can provide more optimization of skills. In a decentralized model, you end up having to hire more individuals, as you must replicate specialized skills in multiple areas. 

One aspect that is often overlooked in centralized vs decentralized is pricing power. For compliance, for instance, you can collective bargain auditing to drive better prices in a centralized model. In a decentralized model, every team is determining it’s own bidding and metrics, which basically allows for suppliers to cost every team as individuals, reducing the overall negotiating power of the company. In a decentralized model, you usually also have more junior leaders (as the team and overall scope is smaller), and that dilutes the overall governance credibility, as they are not truly objective, as again, this can give the impression of the fox guarding the hen house.

  1. Is there a clear winner here or is this more of a dogmatic approach / “it depends” type of answer?

Lee: Obviously there is always an “it depends” type of answer, but I personally think a centralized team offers far more advantages than a decentralized team. I have operated in decentralized teams, startups, and heavily matrixed organizations and they have all had incredible inefficiencies, process problems, lack of technological standardization and contention between the leaders in control of the different resources. While anyone can demonstrate leadership, the reality is there can only be one leader for a function. If you want to build a strong and effective security organization my personal recommendation is to avoid the decentralized model and strongly advocate for a consolidated, centralized function for all of the reasons I listed above. 

No matter what size your company is, at some point your business will get big enough that it will either need to transition to or will need to build a centralized security org. Even when your company gets truly massive a centralized security organization will offer tremendous advantages for coordinating the rest of the functions across the business. This doesn’t mean you can’t have specific expertise embedded within the different lines of business, but there should be one overarching function that sets strategy, governance and has the authority to coordinate everything related to security across the organization.

Milan: I am going to lead off with a “it depends”, but “it depends” on what the SLT wants the function of the Compliance team to be, and how they want them to operate. For example, if they want what they “should” want. Corporate SLT should want an independent compliance organization that has the charter and weight to actually drive governance and accountability. Any decisions made by an engineering leader where the compliance team reports directly to them will be suspect if there is an issue, as how can compliance be seen as impartial if the decision can be overturned by the product or engineering leader directly? Did the right conversation happen, does that decision align with similar decisions with other product groups/lines of business? It can be a real problem if there is an issue and companies have to explain.

That is very difficult in a decentralized model. In a decentralized model where the compliance team, which has to drive hard messages and needs to engineering leaders, are they truly independent and will they speak up, as they tend to be mostly more junior, without any real organizational or peer power with the teams they are supposed to govern? The answer I’ve seen is rarely. I’ve seen and worked with many compliance teams that are frankly afraid to raise issues, or particularly escalate (and if they would escalate, who would they escalate to, as it would be their own management that signs their pay stubs). I’ve seen it both on the compliance and security side, where even mid level leaders will not raise or push issues, as they are worried for their jobs. It’s very difficult to find compliance teams and leaders that can truly be “politically unencumbered” in terms of raising issues, when they report to the fox that likely already doesn’t like having to do compliance work. 

I believe that a strong and chartered central team, made up with the right personnel that understand engineering and can translate, and govern engineering compliance practices is the overall best option, particularly for larger organizations where standardization and efficiency must be improved. In a large company, compliance “spokes” with specific charter are important, as it’s the only way to scale the appropriate knowledge down to the teams.

The Different States Of A Security Program

It may be obvious, but every company that has a security program is in a different state of maturity. As a CSO, it is important to recognize and understand what these different states mean in terms of where your energy will be applied. If you are interviewing or hiring into a company, it is critically important to understand what state the security program is in so you can determine if the opportunity is right for you and to ultimately maximize your impact in the role.

The Different States

In general, a security program can be in one of three different states:

  • New / Building
  • Existing / Incremental
  • Shrinking / Decline

New / Building

A security program that is new typically comes along with new companies, startups or possibly new business units that are acquired via acquisition. However, a company may also be establishing a new program if they are found deficient during an audit or if they suffered a security breach. In this state the CSO (or security leader) needs to establish a program from scratch, which will include mapping risks, developing a budget and establishing funding, recommending tools, evangelizing security best practices and hiring a team. There will be a lot of focus on foundational aspects of security like asset inventory, reporting and initial risk baselines for the organization. Your team will also go after initial program certifications like ISO27001, SOC or other compliance activities. You may even need to establish new processes and ways of working.

Here are some good questions to ask to determine if a program is in the new / building state:

  • Who is performing the function of security today?
  • What goals does the organization have in the first year and three years from now?
  • What is the expected annual budget?
  • How many headcount do you expect for the security team in the first year?
  • Where does your company operate and do you expect to have security resources in those geographic regions?
  • What security tooling is in place today (if any)?
  • Does the company have any existing compliance certifications (like SOC, ISO, etc.)?
  • Why is the company focusing on hiring a security leader and building a security program? Did this come about due to a security incident or other security event like a failed audit?
  • What industries does the company do business in? E.g. finance, government, healthcare, etc.

In my experience, establishing a new security program from scratch is a rare opportunity, but if you get the chance it is truly exciting and offers the opportunity for giant leaps forward in terms of security maturity for the company.

Existing / Incremental

The next state of maturity is existing or incremental and most companies will be in this state. In this state a security program has already been established and has the foundations in place in terms of people, processes and technology. Tooling has already been purchased and implemented, an annual budget has been established and a team exists with different functions like security engineering, security operations and security compliance.

An existing security program usually has smaller goals or incremental annual objectives designed to address some specific area of risk that has been outstanding, or to address a new risk area based on business growth. For example, perhaps the organization has an existing Identity and Access Management (IAM) program, but needs to roll out 2-Factor Authentication (2FA) to further secure access. Or, maybe the business is expanding into the financial industry and needs to become PCI-DSS compliant. These are incremental improvements to the security program and will require increases or reallocation of people and budgets.

A CSO or security leader in charge of an existing security program will generally keep things running smoothly, make sure the company doesn’t regress with respect to security maturity and will continually be evaluating the business for new or existing risks that need to be managed.

Here are some questions you can ask if you are interviewing for a new role that will lead an existing security program:

  • What is the annual budget for the security program?
  • What security tools are in place?
  • How is the team structured?
  • What are the security objectives for this year? For three years?
  • What security compliance certifications does the company maintain (e.g. SOC, ISO, etc.)?
  • How many people are in the security team?
  • What functions does the security team perform? (I.e. security engineering, compliance, risk, product security, security architecture, security operations and incident response, etc.)
  • Why are you looking for hire for this role or who am I replacing if I am hired?
  • How do you expect the business to perform over the next year?

Shrinking / Decline

It is an unfortunate reality that not all programs are in the building or existing states. Sometimes security programs shrink or slip into decline. This can be for a number of reasons such as poor leadership or a declining business. A shrinking security program can also be a temporary state that matches normal expansion / contraction of a mature business and the economy. Whatever the reason, leading a declining security program has significant challenges. First, the security leader will need to over communicate the existing risks to the business and make sure budget and headcount reductions match the reduction of risk as the business shrinks. A CSO can run into real trouble if the reductions are arbitrary and leave the business exposed.

Second, you can expect to have to do more with less. As the business contracts your team will still need to perform, but there may not be additional perks such as training, travel, new tooling, etc. You may also need to consider shrinking budgets and reductions in license counts or other tooling.

Another reason for a shrinking / declining security program is during mergers and acquisitions. Depending on how the deal is structured and the capabilities of the acquiring business, your security team may be redundant or parts of your team may no longer be needed.

A shrinking / declining security program isn’t the end of the world, but it does require careful leadership to make sure the risks are managed appropriately and morale doesn’t completely decline and impact the performance of the remaining team.

Not Everyone Is Good In All States

Not everyone will admit it, but the reality is not everyone is good in all states. This shouldn’t be surprising. Startup founders routinely find they can’t scale a company past a certain point and require additional help. Similarly, I have personally experienced that security programs require different leadership depending on the state of the program and the skills of the individual. Some people just can’t scale a program past the building phase and into the incremental phase. Some people don’t know how to handle decline. Leadership skills aside, some people just have a specific preference for what they like to do.

No matter where you are in your professional career or whatever state your security program is in, I hope this post will help you identify and navigate the type of security program you enjoy leading or are looking to lead one day.