Chris Gunner, vCSO at Thrive – a leading NextGen MSP/MSSP, delivering global AI, cybersecurity, cloud, compliance, and digital transformation managed services – on how CISOs can position their cyber strategy to to become part of how a business navigates uncertainty

Quantification of cyber risk is a growing trend. While this can be genuinely useful, in practice it is often misunderstood or over-applied by security leaders. It can range from an arbitrary figure to attempting to model every possible risk on the register in a Monte Carlo simulation. The focus can fall on the mechanics of quantification, rather than how financial decision-makers actually use the information.

Think of the CFO – they don’t walk through every penny in the budget. Instead, they usually focus on the board-level levers that can materially affect the business. These often include three key areas: strategic optionality, removing friction from capital events and avoiding shocks and smoothing operating costs. Security conversations should be anchored the same way.

The Importance of Strategic Optionality

If faced with a credible one-year growth plan, CFOs may recommend a one-year office lease despite a 20% premium. This is because it maintains the option later of moving or re-contracting once the growth trajectory becomes more visible. Like most strategic decisions, it is about preserving flexibility in the face of uncertainty, even if that flexibility comes at a short-term cost.

If we apply this to a cyber context, there are often businesses that have taken a calculated gamble with their existing business strategies. While the plan is sound, there is a chance it might not land as expected. When they require security services, the choice between a ‘standard’ and ‘premium’ SOC frames the decision as one of optionality rather than security spend. Paying more now to preserve the ability to adapt later down the line. A simple illustration is incident response. An on-call retainer with defined response times can look more expensive than ad hoc support. Until an incident occurs and procurement becomes the bottleneck. In those moments, flexibility is often far more valuable than marginal savings achieved earlier.

Removing Friction from Capital Events

For CFOs, especially those operating in the alternative investment space, the focus is on structuring capital events. As opposed to managing day-to-day operational costs. One of the most painful points in that process is due diligence. The careful exchange between acquirer and target that aims to provide enough information for each to price risk, without giving the entire game away.

CISOs can materially influence how smooth or painful that process becomes. The most effective support often comes from understanding upfront what the diligence process will look like and preparing accordingly.

For example, they might develop executive-level ‘Security at ACME’ overviews to sit alongside more detailed trust centre or technical reports. Being available to diligence teams for interviews, and for example clearly articulating which services are outsourced to an MSSP, and why, builds credibility between those executive teams.

Decision-makers often don’t look at penetration test reports at a deal level. They are assessing whether the organisation understands its own control environment. A well-prepared CISO who can clearly explain why certain controls exist acts as a trust amplifier during transactions.

It is often the difference between a diligence process that closes cleanly and one that drifts. Two organisations can have similar maturity. Yet the one that can respond within a day with clear, consistent evidence reduces follow-up questions, avoids uncertainty premiums in pricing discussions and prevents security from becoming a late-stage negotiation point.

Avoiding Shocks and Smoothing Operating Costs

For any individual who has worked with a finance partner to define a departmental budget will know that predictability often takes precedence over absolute cost. Contract value can be secondary to payment terms, renewal timing or the ability to forecast spend with confidence.

CISOs can align with this by looking to reduce unplanned operating expenditure. In addition to understanding the cost structure of their controls by communicating with the technical pre-sales engineer, procurement and account teams.

A good example is cyber insurance. While often purchased directly by finance teams, many policies are relatively off-the-shelf and provide access to services the security team already operates or has under contract. Other policies include notable exclusions for the events most likely to occur. Such as a ransomware incident without business interruption cover. In many cases, these gaps can be addressed in-policy with a flat fee or a more predictable cost model.

The value here extends beyond risk transfer and into more predictable costs: replacing reactive spend with planned expenditure.

Aligning Cyber Conversations to Board Priorities

Across all of the above examples, the common thread is that the board is rarely asking security to prove its value in isolation, and is surprisingly comfortable with uncertainty. But they are asking whether the cyber papers support better decisions, fewer constraints and more predictable outcomes for the business as a whole.

CISOs who frame their priorities in those terms will find their conversations move away from justifying individual controls and towards understanding how security choices shape the organisation’s ability to respond to change. In that context, cyber becomes part of how the business navigates uncertainty, rather than a specialist function defending its budget. Speaking the board’s language, ultimately, is less about converting cyber risk into pounds and pence. It is more about understanding which levers matter at that level and showing how security choices influence them.

Learn more at thrivenextgen.com

  • Cybersecurity
  • Cybersecurity in FinTech
  • Digital Strategy

Ben Francis, Insurance Lead at Risk Ledger, on navigating cyber threats by reinforcing security from the inside out

Cyber insurance has evolved from a straightforward risk transfer mechanism into an integral component of enterprise risk strategy. As a result, the conversation has shifted beyond simply securing coverage to embracing three foundational elements: transparency in risk exposure, accountability for security measures, and active collaboration throughout the digital ecosystem.

Rather than asking ‘are you covered?’, the more pertinent question has become ‘can you demonstrate measurable risk reduction?’. Insurers and insureds alike are recognising that what matters now is how well an organisation understands and manages its digital exposure, especially across its extended supply chain. Recent data reveals that 46% of organisations experienced at least two separate supply chain-related cyber incidents in the past year, a clear sign that exposure often lies beyond direct control. 

From Risk Transfer to Risk Visibility 

In recent years, the cyber insurance market has matured significantly. Once viewed as a reactive safety net to cushion the financial impact of attacks, it is now becoming a proactive tool for managing and mitigating risk. This shift is partly driven by insurers, who increasingly expect and work with organisations to demonstrate strong security practices and a nuanced understanding of their threat landscape, including risks deep within their digital supply chains; an area where many businesses still fall short.

At the same time, the industry faces a growing challenge from systemic cyber risk within their portfolios, as many businesses rely on the same cloud providers, payment systems and digital platforms, increasing the chance of a single point of failure. Insurers must gain visibility into how policyholders are connected, not only to suppliers but to each other. Tools and frameworks that map and monitor these interconnections will be essential to avoid underestimating the wider impact of seemingly isolated cyber events.

Mapping Beyond Third Parties

It is no secret that cyber attackers often target the weakest link in a supply chain. These are not always direct suppliers, but fourth, fifth or even sixth-tier vendors that have indirect but critical access to systems and data. Unfortunately, many organisations lack visibility beyond their first tier, creating blind spots that attackers can easily exploit. From an insurance perspective, this presents a clear challenge. If an organisation cannot account for who it is connected to, it cannot adequately quantify its risk and neither can its insurer. Mapping these extended connections is more than just a technical exercise; it means actively practiced risk governance and responsibility. Insurers increasingly want to know how their policyholders are identifying and managing indirect dependencies, particularly in sectors like financial services and retail where disruption can ripple across entire markets.

Collaboration as a Risk Strategy 

One of the more underappreciated aspects of cyber resilience is the role of peer collaboration. Unlike physical incidents, cyber threats rarely exist in isolation. A single compromised vendor can impact multiple organisations simultaneously, a fact that has been highlighted by high-profile supply chain attacks such as SolarWinds and MOVEit

As a result, businesses need to think beyond their own perimeters and adopt a more collective mindset. This includes building relationships with industry peers, sharing threat intelligence and participating in sector-wide initiatives aimed at improving visibility and preparedness. 

In highly regulated sectors, such as insurance, this collaboration is increasingly being encouraged by oversight bodies. Frameworks like the Digital Operational Resilience Act (DORA) in the EU and initiatives from the Prudential Regulation Authority (PRA) and the Financial Conduct Authority (FCA) in the UK are pushing for more transparency around third-party risk. In this context, openness is no longer optional; it will be a regulatory expectation. 

For insurance providers, greater collaboration between policyholders also means better data on emerging threats and more accurate portfolio management. For businesses, it offers a chance to anticipate vulnerabilities that may not yet have hit their own networks but are affecting others in their industry. 

Proactive Transparency Builds Trust 

Organisations that take a proactive, transparent approach to cyber risk management are more likely to secure cover and potentially favourable terms, not just in terms of premiums, but also in access to additional services such as forensic support, incident response sources and legal counsel. 

Demonstrating a mature cyber posture is not about claiming perfection. No organisation is immune to breaches. What insurers are looking for is evidence of a structured approach: the existence of incident response plans, robust governance, effective supply chain risk management, and above all, an honest view of risk. 

A Shift in Mindset 

Ultimately, our understanding of cyber insurance must keep evolving. It should not be treated as a simple checkbox exercise, but as a collaborative relationship between insurers and the organisations they support – one built on shared insight, clear communication, and a drive for continuous improvement.

The organisations best equipped to navigate today’s threats will be those that prioritise transparency. Not only does it lead to stronger protection, but it also builds a culture of accountability that reinforces security from the inside out.

Learn more at riskledger.com

  • Cybersecurity
  • Cybersecurity in FinTech
  • Digital Strategy
  • Fintech & Insurtech
  • InsurTech