General Douglas MacMarthur said “never give an order that can’t be obeyed”. This is sound advice, as doing so can diminish the commander’s authority. If people want to do what you are asking them to do, but can’t, they would doubt your judgement in the future.
Despite the fact that most of us operate in commercial organisations rather than the US Army, there are some lessons to be learned from this.
Security professionals don’t need to rally their troops and rarely operate in command-and-control environments. Their role has largely shifted to the one of an advisor to the business when it comes to managing cyber risk. Yet all too often advice they give is misguided. In an effort to protect the business they sometimes fail to grasp the wider context in which it operates. More importantly, they rarely consider their colleagues who will have to follow their guidance.
Angela Sasse gives a brilliant example of this when she talks about phishing. Security professionals expect people to be able to identify a phishing email in order to keep the company secure. Through numerous awareness sessions they tell them how dangerous it is to click on a link in a phishing email.
Although it makes sense to some extent, it’s not helpful to expect people to be able to recognise a phishing email 100% of the times. In fact, a lot of information security professionals might struggle to make that distinction themselves, especially when it comes to more sophisticated cases of spear phishing. So how can we expect people who are not information security specialists to measure up?
To make matters worse, most of modern enterprises depend on email with links to be productive. It is considered normal and part of business as usual to receive an email and click on the link in it. I heard of a scenario where a company hired an external agency and paid good money for surveying their employees. Despite advance warnings, the level of engagement with this survey was reduced as people were reporting these external emails as “phishing attempts”. The communications team was not pleased and that certainly didn’t help establish the productive relationship with the security team.
The bottom line is that if your defences depend on people not clicking on links, you can do better than that. The aim is not to punish people when they make a mistake, but to build trust. The security team should therefore be there to support people and recognise their challenges rather than police them.
After all, when someone does eventually click on a malicious link, it’s much better if they pick up the phone to the security team and admit their mistake rather than hope it doesn’t get noticed. Not only does this speed-up incident response, it fosters the role of the security professional as a business enabler, rather than a commander who keeps giving orders that can’t be obeyed.
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.
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.
Remember, the above is just an indicative timeline. The reality will very much depend on your organisation’s priorities, maturity and resource availability.
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.
- 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.
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.
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.
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.
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.
Cyber security is a manpower constrained market – therefore the opportunities for AI automation are vast. Frequently, AI is used to make certain defensive aspects of cyber security more wide reaching and effective: combating spam and detecting malware are prime examples. On the opposite side there are many incentives to use AI when attempting to attack vulnerable systems belonging to others. These incentives could include the speed of attack, low costs and difficulties attracting skilled staff in an already constrained environment.
Current research in the public domain is limited to white hat hackers employing machine learning to identify vulnerabilities and suggest fixes. At the speed AI is developing, however, it won’t be long before we see attackers using these capabilities on mass scale, if they don’t already.
How do we know for sure? The fact is, it is quite hard to attribute a botnet or a phishing campaign to AI rather than a human. Industry practitioners, however, believe that we will see an AI-powered cyber-attack within a year: 62% of surveyed Black Hat conference participants seem to be convinced in such a possibility.
Many believe that AI is already being deployed for malicious purposes by highly motivated and sophisticated attackers. It’s not at all surprising given the fact that AI systems make an adversary’s job much easier. Why? Resource efficiency point aside, they introduce psychological distance between an attacker and their victim. Indeed, many offensive techniques traditionally involved engaging with others and being present, which in turn limited attacker’s anonymity. AI increases the anonymity and distance. Autonomous weapons is the case in point; attackers are no longer required to pull the trigger and observe the impact of their actions.
It doesn’t have to be about human life either. Let’s explore some of the less severe applications of AI for malicious purposes: cybercrime.
Social engineering remains one of the most common attack vectors. How often is malware introduced in systems when someone just clicks on an innocent-looking link?
The fact is, in order to entice the victim to click on that link, quite a bit of effort is required. Historically it’s been labour-intensive to craft a believable phishing email. Days and sometimes weeks of research and the right opportunity were required to successfully carry out such an attack. Things are changing with the advent of AI in cyber.
Analysing large data sets helps attackers prioritise their victims based on online behaviour and estimated wealth. Predictive models can go further and determine the willingness to pay the ransom based on historical data and even adjust the size of pay-out to maximise the chances and therefore revenue for cyber criminals.
Imagine all the data available in the public domain as well as previously leaked secrets through various data breaches are now combined for the ultimate victim profiling in a matter of seconds with no human effort.
When the victim is selected, AI can be used to create and tailor emails and sites that would be most likely clicked on based on crunched data. Trust is built by engaging people in longer dialogues over extensive periods of time on social media which require no human effort – chatbots are now capable of maintaining such interaction and even impersonate the real contacts by mimicking their writing style.
Machine learning used for victim identification and reconnaissance greatly reduces attacker’s resource investments. Indeed, there is even no need to speak the same language anymore! This inevitably leads to an increase in scale and frequency of highly targeted spear phishing attacks.
Sophistication of such attacks can also go up. Exceeding human capabilities of deception, AI can mimic voice thanks to the rapid development in speech synthesis. These systems can create realistic voice recordings based on existing data and elevate social engineering to the next level through impersonation. This, combined with other techniques discussed above, paints a rather grim picture.
So what do we do?
Let’s outline some potential defence strategies that we should be thinking about already.
Firstly and rather obviously, increasing the use of AI for cyber defence is not such a bad option. A combination of supervised and unsupervised learning approaches is already being employed to predict new threats and malware based on existing patterns.
Behaviour analytics is another avenue to explore. Machine learning techniques can be used to monitor system and human activity to detect potential malicious deviations.
Importantly though, when using AI for defence, we should assume that attackers anticipate it. We must also keep track of AI development and its application in cyber to be able to credibly predict malicious applications.
In order to achieve this, a collaboration between industry practitioners, academic researchers and policymakers is essential. Legislators must account for potential use of AI and refresh some of the definitions of ‘hacking’. Researchers should carefully consider malicious application of their work. Patching and vulnerability management programs should be given due attention in the corporate world.
Finally, awareness should be raised among users on preventing social engineering attacks, discouraging password re-use and advocating for two-factor-authentication where possible.
The Malicious Use of Artificial Intelligence: Forecasting, Prevention, and Mitigation 2018
Cummings, M. L. 2004. “Creating Moral Buffers in Weapon Control Interface Design.” IEEE Technology and Society Magazine (Fall 2004), 29–30.
Seymour, J. and Tully, P. 2016. “Weaponizing data science for social engineering: Automated E2E spear phishing on Twitter,” Black Hat conference
Allen, G. and Chan, T. 2017. “Artificial Intelligence and National Security,” Harvard Kennedy School Belfer Center for Science and International Affairs,
Yampolskiy, R. 2017. “AI Is the Future of Cybersecurity, for Better and for Worse,” Harvard Business Review, May 8, 2017.
Image by fdecomite.
When determining the level of maturity of a security function, I focus on the following areas and try to answer these questions:
- Is security strategy aligned with business strategy (including vision and mission)?
- Is it documented and communicated?
- Is it supported by the leadership?
- Is there a guiding policy in place to achieve set objectives?
- Have accountable individuals been identified?
- Have risk management practices been established?
- Have audit and assurance practices been established?
- Have performance measurement practices been established (including KPI definition)?
- Have global and regional interfaces been defined?
- Has team structure and funding been agreed?
The focus of many of my projects is on risks. I’ve observed through multiple assessments in various companies and industries a lack of formalised risk management process. Some of the plans may exist but they are not linked to specific risks and risk reduction levels are not being measured and reported on appropriately.
The security function can be effective in responding to incidents but the strategic risk-driven planning is often missing. The root cause of this state of affairs is often can be generalised as low maturity of the security function. If that’s the case, the team spends most of its time fighting fires and have little capacity to address the challenges that cause these fires in the first place.
To address this, I assess current state of the security function, define the target maturity level and then develop a high-level roadmap to achieve that desired state.
If the company is geographically distributed, noticeable differences usually exist between a number of business units in terms of overall policy framework. The suggestion here is to define a baseline level of security controls across the entire enterprise. The first step in defining these is to understand what we are trying to protect – the assets.
Modern corporations own a wide range of assets that enable them to operate and grow. They broadly include physical and non-physical assets, people and reputation. Engagement from appropriate parts of the business to identify these is important here as potential attacks to these assets might negatively affect the operations.
By understanding the assets we are able to better identify risks, enable effective detection and response, and prioritise controls and remediation efforts better.
It also helps to conduct a bottom-up review of assets to understand what exactly we’ve got there, focusing on the most critical ones and creating and updating asset inventories.
Understanding the asset base and setting standards and guidance for protecting them will focus the efforts and help you prevent and better respond to security issues.
Assets are tightly linked to threat actors, because it’s not enough to know what we need to protect – we also need to know what we are protecting our assets against. Threat actors vary in their motivation and ability and – depending on the company – include nation states, organised crime, insiders, hacktivist, competitors, etc.
A combination of assets and threats helps us to define risks.
Identifying risks and placing them on a heat map helps determine the inherent, residual and target risks. Inherent risks show the level of risk assuming all the controls or remediating measures were absent or failing. Think of it as if security function didn’t exist. It’s not a happy place where we see the majority of risks have high impact and likelihood being in the top right hand side corner of the chart.
Luckily, security function does exist and even if they don’t have a formalised risk management process, they are usually doing a good job in addressing some of these risks.
Current level of risk is taking into account all the controls and remediating measures in place. The initial impact and likelihood is usually reduced and sometimes to an acceptable level agreed by the business. The idea here is although further reduction of impact and likelihood is possible, it might not be cost-effective. In other words, the money might be better spent in addressing other risks.
Target risks is the future state risk level once additional controls and remediation measures are implemented by the security team.
The main takeaway here is that a formalised risk management approach (with accompanying processes and policies) is needed to ensure all risks are identified and tracked over time, and the appropriate resources and efforts are spent on the top priority risks.