Client portfolios worth millions often sit within cloud environments that appear stable on the surface. Gianna Maldonado, founder of Rebuild I.T., believes those environments frequently carry unseen vulnerabilities that only emerge under pressure. In her view, a breach in wealth management does not remain confined to systems; it extends into trust, fiduciary responsibility, and the safety of highly sensitive client data.
Maldonado points to studies that highlight cloud misconfiguration as a significant cause of cloud security breaches, with 36% of companies suffering a serious cloud security leak. In addition, 99% of all firewall breaches are caused by misconfigurations. She sees these patterns as evidence that many failures originate at the foundational level before they are ever instigated by sophisticated attacks.
Within wealth management, where firms store personal identifiers, financial records, and long-term investment data, she considers those gaps particularly consequential. Her response to this landscape takes shape through what she calls a “destroy it, then rebuild it” framework. The philosophy, as Maldonado explains, emerged from the realization that many organizations either test their systems superficially or attempt to secure them without fully understanding how they fail. Her model is designed to address both sides of that gap.
“We’re going to come into your company and completely hack your systems, whether that’s from an internal perspective or as an external threat actor. The goal is to find everything that can break your company,” Maldonado explains.
The process involves simulating real-world attack scenarios to uncover vulnerabilities across cloud environments, internal networks, and user access points. Maldonado frames the outcome as a detailed report that outlines what can be accessed and what those access points could mean if leveraged by a malicious actor. She notes that even organizations that choose not to engage further leave with a structured roadmap of identified risks.
Patterns within the wealth management sector, in Maldonado’s view, contribute to recurring vulnerabilities. She notes a surge in fintech innovation, where financial professionals build technology platforms that may not yet meet security or compliance expectations. At the same time, she observes that many established firms continue to rely on legacy infrastructure, including systems written in older programming languages.
According to Maldonado, this combination creates an uneven security landscape. New systems may move quickly without sufficient safeguards, while older systems may lag behind evolving threat models. She believes both conditions increase exposure, particularly when modernization efforts proceed without a parallel focus on cybersecurity readiness.
Misaligned priorities also play a role. Maldonado often sees firms investing in advanced security tools while overlooking basic controls. She says, “If you don’t have your foundations, then you’re putting a lock on a house with a broken window.”
She frequently points to email security, patch management, and access controls as areas that require consistent attention. In her assessment, these entry points remain among the most commonly exploited, largely because they are underestimated in favor of more complex solutions.
Once vulnerabilities are identified, Maldonado’s approach shifts toward rebuilding systems with a stronger foundation. This phase includes reconfiguring cloud environments, aligning IT processes, and integrating security into operational workflows. She views this as an opportunity to move beyond reactive fixes and toward a more structured security solution.
With the continuous testing cycle that follows, Maldonado frames it as an essential component of her model, where systems are repeatedly challenged after remediation. “Everything we fix, we retest,” she explains. “Can you break this? Can you find another way in? That cycle continues until the system holds.”
This iterative process, in her view, reflects how real-world attackers behave. “Rather than a single attempt, they explore multiple pathways, adapting to defenses as they encounter them,” she explains, highlighting that security strategies should mirror that persistence.
In the upcoming years, she sees the threat landscape evolving rapidly with the integration of artificial intelligence. Maldonado points to recent developments where AI systems have identified longstanding vulnerabilities at a pace that would be difficult for human analysts to match. She expects both defenders and threat actors to increasingly rely on these tools, creating a more dynamic and competitive environment.
Maldonado emphasizes the importance of clear communication around risk and impact. “Clients need to understand the business impact of cybersecurity,” she notes. “At the very least, understand that their data should not be widely available on the internet.”
She also sees a broader shift taking place in how organizations evaluate cybersecurity. In her view, firms are placing greater emphasis on finding trusted advisors who can assess technical vulnerabilities and the overall state of IT operations. This includes addressing inefficiencies, reducing reliance on undocumented processes, and creating systems that can be understood and maintained over time.
Wealth management firms that choose not to examine their systems in this way, she suggests, may be relying on assumptions instead of evidence. At Rebuild I.T., Maldonado’s framework ultimately centers on visibility and accountability. By intentionally exposing weaknesses and rebuilding systems with those insights in mind, she believes organizations can gain a clearer understanding of their risk landscape.
