Traditional security approaches have become unsustainable for technology leaders navigating today’s complex threat landscape. Information risk management is no longer a checkpoint at the end of development but must be woven throughout the entire software delivery lifecycle. As regulators demand more tangible evidence of security controls and compliance, organizations must fundamentally transform how they approach risk — shifting from reactive gatekeeping to proactive enablement.
“Regulators today are no longer satisfied with frameworks, documentation, and audit validation alone; they want tangible evidence, including end-to-end testing, as well as compliance program management that is baked into day-to-day operating processes.” — 2025 Banking Regulatory Outlook, Deloitte
The stakes are clear. In today’s digital economy, business objectives like “becoming a trusted financial partner” or “protecting customer data while driving innovation” require more than technical controls and documentation. They demand a reimagining of how we integrate security and compliance into every stage of software delivery.
Key takeaways:
- Traditional security approaches focused on late-stage gatekeeping are failing to meet modern business and regulatory needs
- Successful transformation requires a shift from “security guard” to “trusted advisor” mindset
- Four critical foundations drive success: collaboration, automation, visibility, and prevention
- Measuring security posture through clear metrics enables data-driven risk management
- Cultural transformation and capability development are as crucial as technical controls
Expected benefits:
- Reduced security-related delays in software delivery
- Decrease in post-release vulnerabilities and incidents
- Lower remediation costs through early detection
- Improved regulatory compliance and audit readiness
- Enhanced collaboration between security and development teams
- Stronger security posture with minimal delivery friction
I. The modern security challenge: Risk in Wonderland
In Lewis Carroll’s “Alice in Wonderland,” the Queen of Hearts famously declares, “Sentence first — verdict afterward.” This absurd approach to justice parallels how many organizations handle security today — enforcing controls after development is complete, when changes are most expensive and disruptive. This approach creates an adversarial relationship where security is perceived as the villain rather than a vital partner in delivering safe, reliable software.
The traditional approach is failing
Imagine a city where building inspections only occur after construction is complete. Developers would face devastating costs when structural issues are discovered too late, leading to expensive remediation or even complete rebuilds. Unfortunately, many organizations still approach information security this way — waiting until development is nearly complete before conducting security reviews, penetration tests, and compliance checks.
The cost of late-stage security
Organizations clinging to traditional security approaches face:
- Costly rework and delayed releases
- Adversarial relationships between security and development
- Mounting security debt
- Increased exposure to threats
- Rising operational risks
- Compliance challenges and regulatory scrutiny
II. The evolution of risk management
Modern information security requires thinking like a trusted advisor rather than a checkpoint guardian. This means creating environments that enable secure development while ensuring system integrity and regulatory compliance.
Shawn McCarthy
From security guard to city planner
| Traditional approach | Modern approach |
|---|---|
| End-stage security reviews | Security in requirements |
| Manual compliance checks | Automated policy enforcement |
| Security as blocker | Security as enabler |
| Project-based security | Product security mindset |
| Perimeter defense | Zero-trust principles |
Now imagine a new world where developers have access to pre-approved security patterns, automated compliance verification, and clear security guidelines that enable rapid, reliable construction while ensuring protection. This is the promise of modern security integration — providing higher-level security building blocks that enable innovation and rapid business reconfiguration while maintaining system integrity. Rather than forcing every team to become security experts, we create platforms and patterns that abstract away complexity while ensuring quality and consistency.
III. The ‘what’: Strategic security alignment
Shawn McCarthy
In an environment where you need to balance business agility with regulatory compliance and security requirements, evolving your security approach is key. Security capabilities need to support rapid delivery of business value while ensuring appropriate protection against threats.
The shift for security teams to focus on business enablement rather than just protection is essential. This means proactively understanding both the business objectives and planned delivery paths, then integrating security seamlessly into those journeys.
Moving to “Shift-Left” security is a significant cultural change. Security is no longer expressed as a gate at the end of development but as an integral part of the entire delivery process. Translating security requirements into actionable guidance and controls allows delivery teams to build secure systems from the start.
Key areas to address:
- Alignment between security capabilities and business risk appetite
- Evolution from security checkpoints to security enablement
- Frameworks for measuring security effectiveness
- Cultural transformation requirements
- Models for effective cross-team collaboration
- Approaches to security investment prioritization
- Automated compliance monitoring
- Secure innovation enablement strategies
Just as a city’s safety depends on building codes being applied from the initial planning stages, our security strategy must be integrated throughout the development lifecycle. This integration ensures that improvements in security posture translate into tangible business value—reduced incidents, better compliance readiness, and stronger customer trust.
IV. The ‘how’: Building secure digital products
1. Security in requirements review
Conversation starter: “How do we ensure security is considered from the very beginning?”
Just as building codes are consulted before architectural plans are drawn, security requirements must be established early in the development process.
| Focus area | Key activities | Business impact |
|---|---|---|
| Risk assessment | – Thorough assessment of controls – Authentication & authorization review – Data protection planning – Input validation requirements |
– Reduced remediation costs – Improved compliance – Enhanced customer trust |
| Architecture review | – Network segmentation planning – Data flow security analysis – Application security architecture – Zero-trust implementation |
– System resilience – Defense in depth – Reduced attack surface – Compliance by design |
| Data classification | – Information classification standards – Appropriate control selection – Privacy requirements mapping – Regulatory alignment |
– Regulatory compliance – Data breach prevention – Appropriate protection levels – Resource optimization |
2. Security in design review
Conversation starter: “How do we identify and address security risks in our architecture?”
Like urban planners considering crime prevention through environmental design, security in design focuses on identifying and mitigating threats early.
| Focus area | Key activities | Business impact |
|---|---|---|
| Threat modeling | – Systematic risk identification – Attack vector analysis – Potential attacker profiles – Business impact assessment |
– Proactive risk mitigation – Targeted security controls – Informed investment decisions – Reduced vulnerabilities |
| Secure patterns | – Pre-approved security patterns – Security reference architectures – Implementation guidelines – Best practice examples |
– Faster development – Consistent security – Reduced design flaws – Knowledge reuse |
| Design reviews | – Security architecture evaluation – Control effectiveness assessment – Design pattern validation – Expert guidance |
– Enhanced design quality – Early flaw detection – Optimized controls – Reduced technical debt |
3. Security in build and test
Conversation starter: “How do we ensure code is secure before it reaches production?”
Similar to building inspections occurring throughout construction, security testing must be integrated into the development process.
| Focus area | Key activities | Business impact |
|---|---|---|
| Secure coding | – Coding standards implementation – Developer security training – Peer code reviews – Security frameworks |
– Fewer vulnerabilities – Developer capability – Consistent quality – Reduced incidents |
| Automated testing | – Static application security testing – Software composition analysis – Secret scanning – Container security scanning |
– Continuous validation – Early detection – Reduced manual effort – Consistent quality |
| Pre-production testing | – Dynamic application security testing – Penetration testing – Compliance validation – Security regression testing |
– Validation of controls – Comprehensive assessment – Regulatory readiness – Risk reduction |
4. Security in production
Conversation starter: “How do we maintain security posture once systems are live?”
Like ongoing city safety monitoring and emergency services, production security ensures systems remain protected against evolving threats.
| Focus area | Key activities | Business impact |
|---|---|---|
| Continuous monitoring | – Security event monitoring – Threat intelligence integration – Anomaly detection – Vulnerability management |
– Rapid threat detection – Proactive protection – Breach prevention – Risk management |
| Incident response | – Response process automation – Playbook development – Cross-team coordination – Recovery procedures |
– Minimized impact – Business continuity – Regulatory compliance – Customer trust |
| Continuous improvement | – Root cause analysis – Control effectiveness review – Process refinement – Knowledge sharing |
– Evolving protection – Process maturity – Reduced recurrence – Organizational learning |
V. Measuring success: The security metrics dashboard
Shawn McCarthy
To effectively manage what you measure, a comprehensive security metrics dashboard should track key indicators across the software delivery lifecycle:
Leading indicators (preventative)
- % of projects with completed threat models before development
- % of developers completing security training
- Code scanning coverage and findings per 1000 lines of code
- Security requirements coverage in user stories
- Security architecture review completion rate
- Third-party component risk assessment completion
Operational indicators (in-process)
- Mean time to remediate security findings
- Security debt reduction rate
- Automated security test pass rate
- Vulnerability scan coverage
- Security gate pass/fail metrics
- Secure coding standard compliance
Lagging indicators (results)
- Production security incidents by severity
- Security findings discovered post-release
- Audit compliance status
- Percentage of applications with current penetration tests
- Average vulnerability age by severity
- Security-related release delays
VI. Practical implementation guide: Down the rabbit hole
Phase 1: Foundation building (1-3 months)
Just as Alice had to understand the rules of Wonderland, start by establishing your security baseline:
- Security maturity assessment across development teams
- Current state risk mapping and gap analysis
- Security governance model definition
- Initial metrics framework establishment
- Pilot team identification and prioritization
- Quick win implementation
Phase 2: Transformation launch (3-6 months)
Like Alice’s journey through Wonderland, begin your transformation expedition:
- Developer security awareness program implementation
- Automated security tooling integration in CI/CD
- Security champions program establishment
- Secure coding guidelines development
- Threat modeling process implementation
- Initial metrics collection and baseline setting
Phase 3: Scale and optimize (6-12 months)
As your journey progresses, expand successful practices:
- Expansion to additional development teams
- Metrics-driven improvement initiatives
- Security automation enhancement
- Advanced threat modeling capabilities
- Developer certification program
- Continuous feedback and optimization loop
VII. The new security mindset: From Queen of Hearts to Cheshire Cat
Shawn McCarthy
A security team’s mindset should evolve from the authoritarian Queen of Hearts, who demands obedience through fear and threatens to remove heads (or projects) that fail to comply, to one that mirrors the Cheshire Cat — providing guidance, appearing when needed, and helping teams navigate their way through the complex security landscape while respecting their autonomy.
The transformation of security leadership
| Aspect | Traditional mindset (“Queen of Hearts”) | Modern mindset (“Cheshire Cat”) | Business impact |
|---|---|---|---|
| Leadership style | – Command and control – Fear-based compliance – Binary pass/fail – Centralized authority |
– Guide and advise – Risk-based decisions – Contextual guidance – Distributed responsibility |
– Faster delivery – Improved collaboration – Better security outcomes – Reduced friction |
| Decision making | – Rigid standards – Manual approvals – Gate-driven process – Risk avoidance |
– Flexible guidelines – Automated validations – Continuous assessment – Risk management |
– Accelerated delivery – Appropriate controls – Consistent protection – Business enablement |
| Team interaction | – Security dictates requirements – After-the-fact reviews – Distant relationship – Approval-based |
– Collaborative design – Embedded security expertise – Partnership model – Enablement-focused |
– Shared responsibility – Earlier detection – Reduced rework – Team empowerment |
Key mindset shifts in practice
1. From enforcer to enabler
| Traditional practice | Modern practice | Value created |
|---|---|---|
| Security gates | Security guardrails | Reduced delivery friction |
| Manual security reviews | Self-service security tools | Faster development cycles |
| Audit-driven compliance | Risk-based protection | Appropriate security investment |
| Security sign-offs | Automated validations | Continuous compliance |
2. From documentation to automation
| Traditional practice | Modern practice | Value created |
|---|---|---|
| Manual compliance evidence | Automated evidence collection | Reduced audit overhead |
| Static security requirements | Security as code | Consistent implementation |
| Periodic security testing | Continuous security validation | Earlier vulnerability detection |
| Human-dependent controls | Machine-enforced controls | Scalable security |
3. From project to product security
| Traditional practice | Modern practice | Value created |
|---|---|---|
| Point-in-time assessments | Continuous security monitoring | Sustainable security posture |
| Handover to operations | Shared security responsibility | Improved operational security |
| Final penetration tests | Frequent security testing | Earlier vulnerability detection |
| Security debt accumulation | Continuous security improvement | Reduced security incidents |
VIII. Shifting left in practice: The golden pathway
Shawn McCarthy
Building on the concept of a “golden path” for software development, we can establish a “secure golden pathway” that integrates security at every stage of the software delivery lifecycle.
Before development
Activities:
- Information classification validation
- Third-party risk assessment
- Security architecture review
- Authentication/authorization design
- Threat modeling
Who: Information risk management, architecture, product Teams
How: Local governance with security expertise
Goal: Build security requirements into development backlogs
During development
Activities:
- Secure coding practices
- Pre-commit security checks
- Static application security testing
- Software composition analysis
- Secret scanning
- Security-focused code reviews
Who: Developers, security champions, appsec engineers
How: Automated tooling in CI/CD pipeline
Goal: Detect and fix vulnerabilities early in development
Before release
Activities:
- Dynamic application security testing
- Penetration testing
- Infrastructure security validation
- Compliance verification
- Final security review
Who: Application security, quality assurance, devops
How: Automated security gates with clear remediation paths
Goal: Validate security controls before production deployment
In production
Activities:
- Security monitoring and alerting
- Vulnerability management
- Incident response readiness
- Security metrics tracking
- Continuous improvement
Who: Operations, security operations, product teams
How: Shared responsibility model with clear accountabilities
Goal: Maintain security posture throughout product lifecycle
IX. The integrated future: DevSecOps maturity
As your organization matures, security becomes truly embedded in the development process, leading to a fully integrated DevSecOps approach.
Shawn McCarthy
Characteristics of DevSecOps maturity
| Dimension | Initial level | Intermediate level | Advanced level |
|---|---|---|---|
| Culture | – Security as separate function – Compliance-driven – Reactive approach |
– Security champions program – Cross-team collaboration – Proactive mindset |
– Shared responsibility – Security enablement – Innovation-friendly |
| Automation | – Basic scanning tools – Manual approval gates – Limited integration |
– Integrated security tooling – Automated security gates – Self-service options |
– Comprehensive automation – Policy as code – Preventative controls |
| Measurement | – Vulnerability counts – Audit findings – Manual reporting |
– Security debt tracking – Process metrics – Automated dashboards |
– Risk-based metrics – Business impact measures – Predictive analytics |
| Governance | – Traditional security policies – Manual compliance checking – Centralized control |
– Modern security standards – Automated compliance – Federated governance |
– Adaptive policies – Continuous compliance – Distributed ownership |
Advanced security integration techniques
As you advance in maturity, explore these advanced security integration techniques:
- Infrastructure as Code (IaC) security
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- Security as code
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- Continuous compliance monitoring
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- Self-service security
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X. Conclusion: Navigating the risk landscape
The transformation from reactive security to “Shift-Left” risk management represents more than a change in methodology — it’s a fundamental reimagining of how we create and sustain secure business value through technology. Just as thriving cities integrate safety considerations from urban planning through construction and ongoing operations, our development approach must transform from late-stage security testing to integrated risk management that enables continuous secure innovation.
Vision of the transformed enterprise
- Security that accelerates rather than constrains innovation
- Automated controls that ensure compliance without manual intervention
- Transparent security metrics guiding risk-based decisions
- Engaged teams sharing security responsibility
- Architecture designed for protection without compromising agility
- Strong security foundations that enable continuous compliance
In the process, security teams step out from the enforcement role — like the Queen of Hearts — and into a role more akin to the helpful but unobtrusive Cheshire Cat. By fostering collaboration, contextual guidance, and continuous improvement, you’ll build not just secure technology solutions, but a resilient digital ecosystem that can adapt to tomorrow’s threats.
Key takeaways for technology leaders
- Start with business risk appetite, not just technical controls
- Align security metrics with business outcomes for meaningful insights
- Provide security platforms and patterns that make secure development easy
- Measure what matters — tie security metrics to business impact
- Invest in security capabilities and culture across the organization
- Design for secure evolution using automated compliance and verification
- Continuously share insights and scale successful security patterns
Remember, just as great cities aren’t built in a day, this transformation is a journey rather than a destination. The key is to start now, move purposefully, and keep the focus on enabling business outcomes while ensuring appropriate protection. In doing so, you’ll build not just a secure technology landscape, but a thriving ecosystem that powers your organization’s future success — safely and confidently.
Call to action: Starting your transformation
- Assess your current security integration maturity
- Identify your most pressing security improvement opportunities
- Build a coalition of business, technology, and security leaders
- Choose a high-impact pilot area for initial focus
- Establish clear metrics for measuring security improvement
- Share successes and learnings broadly
- Scale proven patterns across the organization
- Maintain focus on continuous security improvement
Organizations that successfully navigate this transformation will build competitive advantages through faster, more secure software delivery, more efficient use of security investments, improved ability to meet regulatory requirements, enhanced capacity for secure innovation, and greater business-security alignment.
The time to start is now. Your organization’s future security posture depends on the foundations you build today.
Shawn McCarthy is vice president and chief architect, Global Architecture, Risk & Governance, at Manulife.
This article was made possible by our partnership with the IASA Chief Architect Forum. The CAF’s purpose is to test, challenge and support the art and science of Business Technology Architecture and its evolution over time as well as grow the influence and leadership of chief architects both inside and outside the profession. The CAF is a leadership community of the IASA, the leading non-profit professional association for business technology architects.
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