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Measuring Your Offensive Security Maturity

Perfect Your Processes

By Nick Popovich, PlexTrac Hacker in Residence

No matter how talented the cyber team or how sophisticated the technologies, bad actors can still gain the upper hand without the presence of mature processes. Establishing clear objectives and having well-documented, strictly followed procedures are key to developing an effective security program and improving performance. Process management may not be the most thrilling aspect of program building, but it is undeniably essential to maturing a security program.

Organizations need to invest their time and resources in establishing and enhancing processes in order to remain competitive and efficient. Having well-defined processes can improve operational efficiency, reduce costs, and ensure compliance with organizational policies and best practices. Establishing and enhancing processes also helps organizations create and maintain a consistency in the execution of excellence.

PlexTrac exists to help offensive teams become more efficient and effective so organizations can become more proactive and ultimately, more mature. Check out our webinar series with Echelon Risk + Cyber to learn more about leveling up your offensive security game, and don’t miss the episode on Perfecting Your Processes.

Now let’s deep dive into effective strategies to enhance the processes that organizations rely on. 

Document Your Security Processes

Developing and documenting a strategy, mission, and goals is essential for offensive security teams — or organizations — to have a successful future. Without putting pen to paper, goals can be nebulous, strategies can morph or waver, and leadership may appear haphazard. As you brainstorm ideal goals for your security group that align with overarching organizations goals, you are also providing accountability. It’s tough to check if your trajectory is aligned with your goals if you’ve never set them. Once set and documented, you can go about establishing other procedural and process elements that coincide with the objectives of your documented goals.

Next you need to form a strategy, perhaps at multiple levels that aids team members by aligning their day-to-day and operations with the goal that was previously established. Ideally, your strategic map is a plan of action that will guide those who follow it in achieving set objectives. Establishing key performance indicators (KPIs) and goals at every level of process are important because they are the measurable outcomes that will be used to assess if the strategy and mission have been successful. Documenting these elements will help ensure that everyone in the organization is on the same page and working towards the same objectives.

Align Your Team’s Security Processes

Aligning a strategic vision or mission to an actionable plan is a critical step towards transforming a vision into a tangible reality. To do this, the vision must be broken down into smaller, more achievable goals with a plan of action created for how to reach them. This plan should be detailed, taking into account tasks, resources, timelines, and roles and responsibilities to ensure everyone understands the role they play in the process. Moreover, a system of feedback and accountability must be established in order to measure progress and maximize the chances of success. Additionally, providing a system of feedback and accountability is critical to measure progress and ensure the plan is successful. Think of this as a feedback loop. You execute, analyze, refine, and repeat. As you refine your processes will continue to align more closely and effectively with your organizational mission or goals.

Sometimes, thinking with a lens of strategic, tactical, and operational effectiveness is useful when deciding how to align teams and processes.

Operational plans are the day-to-day activities that are necessary to achieve an organization’s goals. Examples of operational plans include developing processes and procedures, assigning tasks to employees, and creating a budget. 

Tactical plans are short-term plans that are developed to achieve specific goals or objectives within a certain timeframe. These plans are often used to support the execution of the organization’s strategic plan. Examples of tactical plans include developing marketing campaigns, product launches, and sales initiatives. 

Strategic plans are long-term plans that are developed to guide an organization over an extended period of time. They typically focus on the organization’s overall objectives and direction. Examples of strategic plans include setting priorities, developing a vision and mission statement, and creating a business plan.

Execute Using Your Standardized Security Processes

Executing on processes consistently is essential for offensive security teams. If everyone goes rogue it makes it significantly more difficult to onboard new people. It also makes it difficult to know who needs help, and how they need it. Successful security teams implement the right tools and training to ensure everyone is on the same page and following the same processes. This includes leveraging automation and management tooling where relevant, including task management, reporting and workflow applications, to streamline and automate processes and tasks. It also includes providing (or… GASP… paying for) training to ensure everyone has access to the skills they need to be successful. 

Consider these concepts below, that high performing teams seem to share in common regarding executing excellence:

  • Clear roles and responsibilities: Ensure that everyone on the team knows what they’re responsible for and the tasks they must complete.
  • A culture of accountability: Make sure that team members understand the importance of following correct processes while meeting deadlines.
  • Facilitate and leave room for collaboration: Give team members the space to share ideas and work together.
  • Utilize feedback loops: Ask for input from team members on how to improve processes and use their feedback as a basis for training.
  • Invest in the team: Provide training and educational resources that allow team members to expand their skills and enhance their understanding of processes.
  • Leverage technology: Use technology to automate processes and make them more efficient.
  • Develop a systematic approach: Create a step-by-step approach to process execution that ensures that all team members are following the same protocol.
  • Reward progress: Celebrate successes and recognize team members who are making progress.

Measure Your Security Team’s Effectiveness

Building in checkpoints and evaluation is an important part of any security strategy and plan. This allows the organization to assess the progress and effectiveness of the strategy and make changes if necessary. A good way to assess your progress is scheduling regular meetings with key stakeholders to review progress, collecting feedback from customers and employees, and tracking analytics to measure quantitative performance. This data can then be used to adjust the strategy and ensure it is meeting the organization’s goals.

Checkpoints are a great way to measure the progress of offensive security teams. By setting checkpoints throughout the team’s timeline it allows the team to accurately track their progress and make sure they are meeting their goals and objectives. Checkpoints can be at multiple levels, as well. Perhaps there are project based tag ups for status, monthly meetings to get a broader view, and quarterly checks to ensure the teams or individual is aligned appropriately. Additionally, checkpoints can help identify any areas of improvement and provide insight into any areas of weakness. 

Evaluations are an important tool for measuring the progress of offensive security teams. These are done at a higher level than checkpoints, and help determine the value of a process or goal. Also, it’s a time to ensure that previously established goals are still relevant to success. Evaluations can be used to provide feedback on successes and failures, as well as identify any areas of improvement. They should be conducted at regular intervals and should include input from the team members, managers, and other stakeholders. Additionally, evaluations should review the progress of objectives, timelines, and any other relevant metrics. 

The PlexTrac Solution

The PlexTrac platform can be used as an aid in measuring the maturity and efficacy of offensive security testing efforts and teams. It is designed to provide data on findings’ status, allow teams to collaborate effectively, and provide analytical insights into trends on the data derived from the testing efforts. 

PlexTrac is a force multiplier for offensive security programs. Book a demo to learn how PlexTrac can accelerate your path to maturity. 

Nick Popovich
Nick PopovichPlexTrac Hacker in ResidenceNick Popovich’s passion is learning and exploring technology ecosystems, and trying to find ways to utilize systems in unexpected ways. His career has focused on adversarial threat simulation, offensive and defensive security, and advanced technical security assessments. Nick’s mission is to help individuals and organizations involved with defensive security operations to have an opportunity to observe the mechanics and methods of the attackers they’re defending against, and to assist in realistically testing those defenses. He’s a lifelong learner and loves finding new ways to get under the hood of systems and networks. He is a father of three and a husband to one.

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