The Complexity of Risk Management – free audiobook chapter

My publisher kindly made one of the chapters of my audiobook available for free. In it, I discuss the role of uncertainty in making decisions and managing risk.


How to inventory your AWS assets

Resource

Securing your cloud infrastructure starts with establishing visibility of your assets. I’ll be using Amazon Web Services (AWS) as an example here but principles discussed in this blog can be applied to any IaaS provider.

Speaking about securing your AWS environment specifically, a good place to start is the AWS Security Maturity Roadmap by Scott Piper. He suggests identifying all AWS accounts in your organisation as a first step in your cloud security programme. 

Following Scott’s guidance, it’s a good idea to check in with your DevOps team and/or Finance to establish what accounts are being used in your company. Capture this information in a spreadsheet, documenting account name, ID, description and an owner at a minimum. You can expand on this in the future to track compliance with baseline requirements (e.g. enabling CloudTrail logs).

Once we have a comprehensive view of the accounts used in the organisation, we need to find out what resources these accounts use and how they are configured. We can get metadata about the accounts using CloudMapper’s collect command. CloudMapper is a great open source tool and can do much more than that. It deserves a separate blog, but for now just check out setup instructions on its GitHub page and Scott’s detailed instructions on using the collect command.

The CloudMapper report will reveal the resources you use in all the regions (the image at the top of this blog is from the demo data). This can be useful in scenarios where employees in your company might test out new services and forget to switch them off or nobody knows what these services are used for to begin with. In either case, the company ends up paying for these, so it makes economic sense to investigate, and disabling them will also reduce the attack surface.

In addition to that, the report includes a section on security findings and will alert of potential misconfigurations on the account. It also provides recommendations on how to address them. Below is an example report based on the demo data. 

Findings

As we are just establishing the view of our assets in AWS at this stage, we are not going to discuss remediation activities in this blog. We will, however, use this report to understand how much work is ahead of us and prioritise accordingly.

Of course, it is always a good idea to tackle high criticality issues like publicly exposed S3 buckets with sensitive information but don’t get discouraged by a potentially large number of security findings. Instead, focus on strategic improvements that will prevent these issues from happening in the future.

To lay the foundation for a security improvements programme at this point, I suggest adding all the identified accounts to an AWS Organisation if you haven’t already. This will simplify account management and billing and allow you to apply organisation-wide service control policies.


Cyber security in divestments

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A company may divest its assets for a number of reasons: political, social or purely financial in order to free up resources to focus on core business. Regulators may also demand a divestment to prevent one company holding a monopoly. When such a decision is made, the security function can support the business by managing risks during this process. These risks not only include the obvious legal and regulatory compliance ones, but also risks related to business disruption and leaks of intellectual property or other sensitive information. Security teams can also help the business identify value adding opportunities through, for instance, saving costs on software licenses.

The scale of divestments vary and depend on the nature of the organisation: they can range from a single subsidiary to a whole division. Information usually accompanies physical assets, which opens up potential challenges with data governance when these assets change hands. The magnitude of such risks differ depending on specific conditions of the deal, for example:

  • Number of assets is scope
  • Criticality of assets
  • Location of assets and applicable jurisdictions

In my experience, divestments are almost always associated with aggressive timelines for completion usually in the form of legally binding agreements. Therefore, as a security professional, the last thing you want to do is to slow down the process and prevent the business from meeting these timelines.

You need to balance this, however, with the risk exposure. It helps when the security team gets involved early to support the process from the start. All too often, however, the business can be asking for security sign-off after the finalisation of the deal. This can be disappointing, particularly when a number of data transfer requirements have already been violated.

So if you’re one of the lucky ones, and the business is asking for your advice on divesting securely, what should you tell them? What areas do you consider? Here are some examples to get you started:

  • Information asset inventories and data maps. These might include data, software and infrastructure assets. You can’t help securely transfer something you don’t know exists. Start with establishing visibility and interdependencies.
  • Access control. Who has access to what? Do they need that access? Will they need that access in the future? Segregation of duties and least privilege principles are not just abstract philosophical concepts – they have real applications when it comes to divestments.
  • Consider legal and regulatory requirements when it comes to data asset transfer, retention and disposal. Involve your legal team, but don’t forget about technical controls, like encryption and secure data wipes.
  • Availability of skilled resource and mature IT function on the ‘buy’ side. Remember, whoever is buying the assets must have their infrastructure ready to support the acquisition and integration of new assets. Despite being perceived as a ‘buyer’s problem’, risks like that can negatively impact the overall project and should be considered.

All in all, the divestment process can be challenging but the early integration of security professionals ensures the appropriate oversight is given to all relevant areas for a smooth transfer to the buyer.

Image by Jason Kuffer.


Developing an information security strategy

I wrote previously on how to assess your threat landscape and what your priorities should be when you start developing a security programme in a new company.

In this blog, I would like to dig deeper and talk about how you actually develop a security strategy with some illustrative examples. You can then use these to further refine your security architecture.

As always, we would start with a Why. Why is security important for your business? Well, you will need to help your stakeholders understand that security can help build customer trust and become a brand differentiator.

And how can this be achieved? To keep this simple, let’s zoom in on three priorities:

  • Support the business. Embed security into the business by ensuring alignment to business strategy
  • Risk-based approach. Pragmatic and prioritised security controls, advice, guidance and information security expertise for the business
  • Focus. Centre on protecting the most important assets and understanding the threats

The aim could be to arrive to a state where security underpins all products and services to offer customers a frictionless experience.

Talking to your business stakeholders will help you understand your company’s wider goals and strategy. Let’s imagine for a second that these conversations revealed that your organisation, like many others, ultimately want to grow their revenue. They also identified that the way they are going to grow their revenue is through increasing sales, building customer trust, improving products and services and scaling operations to better meet customers’ needs.

Vulnerable product, misconfigured infrastructure, insecure operations, inadequate compliance regime and inability to withstand incidents all prevent the business from achieving its objectives.

Strategy

You can now prioritise your security activities to align with these objectives, for example by grouping them into product, infrastructure and people security, as well as wider compliance and resilience objectives.

Timeline

Remember, the above is just an indicative timeline. The reality will very much depend on your organisation’s priorities, maturity and resource availability.


The first 100 days as a CISO

Lifecycle

What should you do in your 100 days in a new company? In short, you should find a way to support the business and present it in a way that is understood and accepted. Communicate broadly and often to ensure constant alignment. Measure your progress in a meaningful way to demonstrate the value to the business.

Roadmap

  • Get buy in

Validate top assets, threats and risks. Obtain leadership support on next steps.

  • Baseline where you are

Understand business requirements, technological and regulatory landscape. Perform interviews and review existing product and documentation.

  • Work out what needs to be done

Recommend security improvements to address risks and align with business strategic priorities.

  • Make it happen

Preparing people, establishing good practice and implementing the right technologies and processes.

Timeline.jpeg


Understanding your threat landscape

Identifying applicable threats is a good step to take before defining security controls your organisation should put in place. There are various techniques to help you with threat modelling but I wanted to give you some high-level pointers in this blog to get you started. Of course, all of these should be tailored to your specific business.

I find it useful to think about potential attacks as three broad categories:

1. Commoditised attacks. Usually not targeted and involve off-the-shelf-malware. Examples include:

2. Tailored attacks. As the name suggests, these are tailored and can vary in degree of sophistication. Examples include:

3. Accidental. Not every data breach is triggered by a malicious actor. Therefore, it is important to recognise that mistakes happen. Unfortunately sometimes they lead to undesired consequences, like the below:

Information security professionals can use the above examples in communications with their business stakeholders not to spread fear, but to present certain security challenges in context.

It’s often helpful to make it a bit more personal, defining specific threat actors, their target, motivation and impact on the business. Again, the below table serves as an example and can be used as a starting point for you define your own.

Threat actor Description Motivation Target Impact on business
Organised crime International hacking groups Financial gain Commercial data, personal data for identity fraud Reputational damage, regulatory fines, loss of customer trust
Insider Intentional or unintentional Human error, grudge, financial gain Intellectual property, commercial data Destruction or alteration of information, theft of information, reputational damage, regulatory fines
Competitors Espionage and sabotage Competitive advantage Intellectual property, commercial information Disruption or destruction, theft of information, reputational damage, loss of customer
State-sponsored Espionage Political Intellectual property, commercial data, personal data Theft of information, reputational damage

You can then use your understanding of assets and threats relevant to your company to identify security risks. For instance:

  • Failure to comply with relevant regulation – revenue loss and reputational damage due to fines and unwanted media attention as a result of non-compliance with GDPR, PCI DSS, etc.
  • Breach of personal data – regulatory fines, potential litigation and loss of customer trust due to accidental mishandling, external system compromise or insider threat leading to exposure of personal data of customers
  • Disruption of operations – decreased productivity or inability to trade due to compromise of IT systems by malicious actor, denial of service attacks, sabotage or employee error

Again, feel free to use these as examples, but always tailor them based on what’s important you your business. It’s also worth remembering that this is not a one-off exercise. Tracking your assets, threats and risks should be part of your security management function and be incorporated in operational risk management and continuous improvement cycles.

This will allow you to demonstrate the value of security through pragmatic and prioritised security controls, focusing on protecting the most important assets, ensuring alignment to business strategy and embedding security into the business.


Startup security

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In the past year I had a pleasure working with a number of startups on improving their security posture. I would like to share some common pain points here and what to do about them.

Advising startups on security is not easy, as it tends to be a ‘wicked’ problem for a cash-strapped company – we often don’t want to spend money on security but can’t afford not to because of the potential devastating impact of security breaches. Business models of some of them depend on customer trust and the entire value of a company can be wiped out in a single incident.

On a plus side, security can actually increase the value of a startup through elevating trust and amplifying the brand message, which in turn leads to happier customers. It can also increase company valuation through demonstrating a mature attitude towards security and governance, which is especially useful in fundraising and acquisition scenarios.

Security is there to support the business, so start with understanding the product who uses it.  Creating personas is quite a useful tool when trying to understand your customers. The same approach can be applied to security. Think through the threat model – who’s after the company and why? At what stage of a customer journey are we likely to get exposed?

Are we trying to protect our intellectual property from competitors or sensitive customer data from organise crime? Develop a prioritised plan and risk management approach to fit the answers. You can’t secure everything – focus on what’s truly important.

A risk based approach is key. Remember that the company is still relatively small and you need to be realistic what threats we are trying to protect against. Blindly picking your favourite NIST Cybersecurity Framework and applying all the controls might prove counterproductive.

Yes, the challenges are different compared to securing a large enterprise, but there some upsides too. In a startup, more often than not, you’re in a privileged position to build in security and privacy by design and deal with much less technical debt. You can embed yourself in the product development and engineering from day one. This will save time and effort trying to retrofit security later – the unfortunate reality of many large corporations.

Be wary, however, of imposing too much security on the business. At the end of the day, the company is here to innovate, albeit securely. Your aim should be to educate the people in the company about security risks and help them make the right decisions. Communicate often, showing that security is not only important to keep the company afloat but that it can also be an enabler. Changing behaviours around security will create a positive security culture and protect the business value.

How do you apply this in practice? Let’s say we established that we need to guard the company’s reputation, customer data and intellectual property all the while avoiding data breaches and regulatory fines. What should we focus on when it comes to countermeasures?

I recommend an approach that combines process and technology and focuses on three main areas: your product, your people and your platform.

  1. Product

Think of your product and your website as a front of your physical store. Thant’s what customers see and interact with. It generates sales, so protecting it is often your top priority. Make sure your developers are aware of OWASP vulnerabilities and secure coding practices. Do it from the start, hire a DevOps security expert if you must. Pentest your product regularly. Perform code reviews, use automated code analysis tools. Make sure you thought through DDoS attack prevention. Look into Web Application Firewalls and encryption. API security is the name of the game here. Monitor your APIs for abuse and unusual activity. Harden them, think though authentication.

  1. People

I talked about building security culture above, but in a startup you go beyond raising awareness of security risks. You develop processes around reporting incidents, documenting your assets, defining standard builds and encryption mechanisms for endpoints, thinking through 2FA and password managers, locking down admin accounts, securing colleagues’ laptops and phones through mobile device management solutions and generally do anything else that will help people do their job better and more securely.

  1. Platform

Some years ago I would’ve talked about network perimeter, firewalls and DMZs here. Today it’s all about the cloud. Know your shared responsibility model. Check out good practices of your cloud service provider. Main areas to consider here are: data governance, logging and monitoring, identity and access management, disaster recovery and business continuity. Separate your development and production environments. Resist the temptation to use sensitive (including customer) data in your test systems, minimise it as much as possible. Architect it well from the beginning and it will save you precious time and money down the road.

Every section above deserves its own blog and I have deliberately kept it high-level. The intention here is to provide a framework for you to think through the challenges most startups I encountered face today.

If the majority of your experience comes from the corporate environment, there are certainly skills you can leverage in the startup world too but be mindful of variances. The risks these companies face are different which leads to the need for a different response. Startups are known to be flexible, nimble and agile, so you should be too.

Image by Ryan Brooks.