Bridging the Digital and Cyber Divide: Lessons from Wearing Both Hats - Part 1
Angelo G. Longo
Cybersecurity & GRC Executive | AI Trust & Risk Strategist | Board-Aligned Advisor for Regulated, Cloud-Driven Growth
CIO/CISO Convergence Series #CIOCISOConvergence
Introduction: Bridging the Divide
I cut my IT teeth on NetWare and built a career culminating in engineering data centers with Five 9’s uptime. That hands-on foundation shaped my evolution into cybersecurity, where I advanced through consulting, architecture, and leadership roles before stepping into CISO and vCISO positions. Along the way, I watched the once-clear boundary between CIO and CISO roles erode, replaced by a shared mandate to enable innovation securely, at scale, and with resilience baked in.
This shift has been accelerated by a rapidly evolving landscape: cloud-first architectures, relentless cyber threats, regulatory fatigue, and board-level expectations that technology must drive innovation and resilience. CIOs can no longer execute without security at the core, and CISOs can’t succeed without understanding every recommendation's operational and financial impact.
This article explores where CIOs and CISOs diverge, where they converge, and why the future belongs to those who can confidently bridge both worlds.
Where the Roles Diverge: Understanding the Delta
While CIOs and CISOs sit at the executive table and shape enterprise strategy, their core mandates remain distinct. These distinctions are particularly evident in knowledge domains, performance metrics, and day-to-day priorities.
CIO Knowledge Domains:
CIOs are expected to deliver operational efficiency, digital innovation, and scalable platforms that enable business growth. Their performance is typically measured through uptime, cost containment, delivery velocity, and stakeholder satisfaction.
CISO Knowledge Domains:
CISOs are entrusted with reducing organizational risk, ensuring regulatory alignment, and embedding security into technology and culture. Their success is often measured in avoided incidents, audit performance, maturity of controls, and ability to communicate risk in business terms.
The Delta: Operational Enablement vs. Risk Mitigation
At the heart of the CIO/CISO divergence is what I call "the delta,” a persistent gap in how success is defined, risk is understood, and decisions are prioritized.
These opposing gravitational pulls often result in misaligned priorities, for instance:
Yet both are right, and that tension is healthy—if managed well.
The Stakes Are Rising
In the current environment of supply chain attacks, rising regulatory enforcement, and board-level cyber accountability (e.g., SEC rules on incident disclosure), this delta is more than theoretical—it’s a business risk. Bridging the IT/InfoSec gap requires mutual fluency.
More Reading:
Where They Converge: Strategic Symbiosis
Despite their differences, the most effective organizations foster tight collaboration between CIOs and CISOs. In fact, many of their domains naturally converge—often out of necessity.
Shared Knowledge Areas:
The modern enterprise demands seamless integration of security into operations. As organizations adopt Zero Trust models, move to distributed, cloud-native platforms, and face increased scrutiny from regulators and insurers, the CIO and CISO must work in lockstep. This alignment is not just beneficial, it's foundational to organizational success.
Joint initiatives like secure cloud enablement, federated identity rollouts, and third-party risk governance exemplify this symbiosis. These initiatives reduce risk and improve the enterprise's speed, agility, and confidence when executed well.
This isn’t just alignment for alignment’s sake—it’s the foundation of operational trust. When done right, joint initiatives don’t just reduce risk, they accelerate delivery, strengthen compliance, and build internal credibility.
“Security can no longer be the department of no. It must become a business enabler with a technical backbone—just as IT must become a **strategic differentiator with a security mindset.” — Gartner, 2023
Lessons from Living Both Roles
In my current vCISO work, I frequently assume de facto CIO responsibilities, especially in SMBs or firms transforming. In these environments, the expectation is not a clear-cut division of labor but a blended leadership approach.
I’ve had to:
These experiences have reinforced a critical truth: technical fluency is no longer enough; strategic translation is key. Whether you’re a CIO trying to justify IT investments to the board or a CISO aligning risk postures with business objectives, your impact hinges on your ability to translate across technical, operational, and financial domains.
The next generation of digital leaders won’t ask, "Is this an IT problem or a security issue?" Instead, they’ll ask, "What outcome are we enabling—and how do we do it securely, scalably, and sustainably?"
Acronym Key:
ITSM – IT Service Management
DX – Digital Transformation
CAPEX/OPEX – Capital/Operating Expenditures
ERP – Enterprise Resource Planning
ZTA – Zero Trust Architecture
IRM – Information Risk Management
IAM – Identity & Access Management
SOC – Security Operations Center
BCP – Business Continuity Planning
CSP – Cloud Service Provider
RACI – Responsible, Accountable, Consulted, Informed
GRC – Governance, Risk & Compliance
CIO | IT Executive | Driving Digital Transformation, Scalable Infrastructure & Cybersecurity
3moThank you for sharing. Your article helped me to understand where is the line is. Basically CIO focused on development and innovations, and CISO continuously asking questions about thouse development and innovations: Is it safe, will we risks less with new tech or not, etc ....
I Help Tech Leaders Rise to VP/CxO Roles and Live Their Best Lives | Executive Presence • Influence • Career Acceleration
3moAngelo G. Longo, when I ask CIOs to share their top three concerns, Cybersecurity is at the top. There is so much at risk and the landscape is only getting more complex. Regardless of the blending role, an executive needs to own the concern and everyone in the organization is responsible for keeping their security-related responsibility.
Cybersecurity & GRC Executive | AI Trust & Risk Strategist | Board-Aligned Advisor for Regulated, Cloud-Driven Growth
3moBridging the Delta: 5 Questions CIOs and CISOs Should Ask Each Other - What business outcomes are we enabling, and how can we secure them by design? - Where does our current architecture create friction for users or risk for operations? - How aligned are our KPIs, and should we revisit them together? - Which technologies are we adopting faster than our controls can mature?
Semi-retired pharmaceutical and financial services CISO and healthcare infosec executive. Enjoying everything the Jersey Shore can offer and advising friends and leaders on cybersecurity when the need arises.
3moSpot on Angelo G. Longo ~ this is especially true in the startup space where speed and adaptability is paramount to kickstart the org to the next level.
Chief Information Security Officer – Kontoor Brands | Board of Directors – Retail & Hospitality ISAC | CISSP | NACD.DC | Cybersecurity & Risk Strategist | Enabling Secure Innovation & Business Resilience
3moGreat take, Angelo, I am curious about the articles listed under "More Reading" as I would like to dig into those further, but cannot find them on Gartner or HBR. Would you be able to provide links?