Setting the Stage
The Golden Promise of DevSecOps
Remember when DevSecOps was going to solve all our security problems? That magical moment when development, security, and operations would finally work in perfect harmony, delivering secure software at the speed of business? Yeah, we’re still waiting for that fairy tale ending.
Don’t get me wrong, DevSecOps has brought some real improvements. Teams are talking to each other more, security is being considered earlier in the process, and we’ve made genuine progress in integrating security into development workflows. But if you’re working in a large enterprise, you’ve probably noticed that the golden promise feels more like fool’s gold. The reality is messier, more complicated, and definitely more frustrating than those glossy conference presentations suggested.
What DevSecOps Actually Is (And Isn’t)
Let’s start with what should be obvious but apparently isn’t: DevSecOps isn’t a team you can hire or a tool you can buy. It’s supposed to be a cultural shift; a fundamental change in how organizations think about security, responsibility, and collaboration.
This shift requires ongoing education, adaptation, and most importantly, genuine collaboration across all levels of the organization. It’s about embedding security thinking into every part of the software development lifecycle, making everyone responsible for security rather than leaving it to that one overworked security team who always seems to be the bottleneck.
The idea sounds brilliant on paper. DevSecOps does away with security as the gatekeeper; the kind that ends up being a roadblock and, as a result, gets maligned and misunderstood by the rest of the business. Instead of security being an afterthought or a final checkpoint, it becomes everyone’s job from day one.
But here’s where things get tricky: cultural shifts don’t happen overnight, especially in large organizations where change moves at the speed of continental drift with 10 - 20 years of technical debt and baggage. You can mandate all the collaboration you want, but you can’t mandate trust, understanding, or genuine buy-in.
The Great “Shift Left” Experiment
The first big promise of DevSecOps was “shifting left”, catching security issues early in the development process when they’re cheaper and easier to fix. The philosophy makes perfect sense; why wait until production to discover that your application has more holes than swiss cheese?
Shifting left works beautifully in agile startups where developers can pivot quickly and security teams are embedded with development from the start. Everyone’s in the same room, speaking the same language, and working toward the same goals. It’s DevSecOps as it was meant to be.
But in large enterprises? That’s where reality crashes headfirst into the immovable wall of bureaucracy, compliance requirements, and organizational inertia. These hurdles aren’t just technical, they’re deeply cultural and structural.
Large enterprises often struggle with the speed that shifting left demands. They’re weighed down by compliance, change management, huge technical estates, and risk-averse cultures that treat any change as a potential catastrophe.
Even if you could implement all the security tooling you want (in the enterprise), the ratio of developers to security staff just makes it impossible to move quickly. At best, you are raising more awareness of security issues early in the development process but at worst, you’ve just moved the bottleneck of security to an earlier stage. Either way, I can assure you both development and security teams are frustrated.
The “Shift Right” Alternative
When shifting left proved challenging than expected, some organizations looked to “shift right”; tying security issues found in production back to their source code. The idea was to create complete traceability from a security incident all the way back to the specific code, developer, and decision that caused it.
This concept is even more appealing than shifting left because it promises to close the feedback loop completely. Imagine being able to instantly trace a production security issue back to the exact line of code, the developer who wrote it, and the architectural decision that enabled it. That level of visibility could revolutionize how we think about security, accountability, and learning.
But here’s the catch: this level of traceability requires a tremendous amount of technical and organizational sophistication. You need comprehensive monitoring, near perfect documentation, robust logging, and systems that can correlate data across multiple tools, teams, and time periods. Almost no enterprise organization meets this level of maturity.
We’re living in a world characterized by rapid tool adoption and an ongoing struggle to balance thorough security practices with development speed. We’re drowning in data from dozens of security tools, but we still can’t answer basic questions like “What happens if this service goes down?” or “Who actually owns this piece of code when something breaks at 2 AM?”.
The Bigger Picture We’ve Been Missing
Here’s what I think we’ve gotten fundamentally wrong: we’ve been so obsessed with shifting directions that we’ve missed a fundamental truth. DevSecOps isn’t about moving security left or right; it’s about creating a comprehensive understanding of the people and technology that are responsible for each application.
We face ongoing challenges of integrating security practices without killing agility, and we’re creating complex testing environments that generate more noise and alert fatigue than actionable insights. We’re treating symptoms instead of addressing the root cause, which is a fundamental lack of shared understanding and trust between teams.
Think about the applications in your organization right now. Do you really understand how they’re built? Who the teams are that maintain them? How do they connect to other systems? What are their dependencies? What happens when key people go on vacation or leave the company?
Most organizations can’t answer these basic questions with confidence, yet we expect DevSecOps magic to just happen. We’re trying to optimize processes we don’t fully understand, involving people whose motivations and constraints we haven’t bothered to learn about.
The real solution requires stepping back and mapping the human and technical relationships that make software possible. It means understanding not just the code, but the teams, the processes, the constraints, and the business context that shapes every technical decision.
The Missing Ingredient: Trust
This brings us to the heart of the matter: DevSecOps is really about trust.
When developers don’t trust that security requirements make sense or serve a real purpose, they find creative workarounds. When security teams don’t trust that developers actually care about security beyond lip service, they create more gates, checkpoints, and bureaucratic hoops. When operations teams don’t trust that either group understands production realities, they build their own shadow processes to protect themselves. And when no one understands who owns the application itself…well there are even bigger problems.
This lack of trust creates a vicious cycle where each team optimizes for their own metrics and goals, often at the expense of the overall system. Developers optimize for feature velocity because that’s how they’re measured. Security teams optimize for risk reduction because that’s their mandate. Operations teams optimize for system stability because that’s what keeps them from getting called at 3 AM.
Without trust and shared understanding, these goals don’t just feel mutually exclusive; they actually become mutually exclusive in practice.
Building the Interconnected Future
So how do we rebuild trust and finally fulfill the original promise of DevSecOps? It starts with creating genuine connections that extend beyond individual applications, tools, or processes. It requires us to think bigger than shifting left or right, and instead focus on building systems, both technical and human, that enable trust, transparency, and shared responsibility.
First, we need to invest seriously in shared understanding. This means regular cross-functional sessions where teams don’t just report status updates or share metrics, but actually teach each other about their constraints, goals, and daily challenges. When a security team genuinely understands why developers are pushing for a particular timeline, and developers understand the real-world consequences of the security controls they’re asked to implement, actual collaboration becomes possible instead of just mandated.
Second, we need to make the invisible visible. Map out not just a technical architecture, but a team architecture too. Who depends on whom? Where are the critical handoffs? What are the communication patterns? Where do silos still exist despite org chart claims of collaboration? Often, fixing a technical problem requires first fixing an organizational problem that nobody wants to acknowledge.
Third, we need to measure what matters across teams, not just within teams. Instead of measuring developer velocity, security coverage, and operational uptime as separate, competing metrics, let’s create measurements that reflect shared outcomes. Think “time from idea to secure production deployment” or “mean time to resolve security incidents across all teams involved.”
Fourth, we need to address resistance to change head-on instead of trying to shift around it. That resistance often stems from completely valid concerns about increased workload, unclear accountability, and competing priorities that haven’t been resolved. When you address those concerns directly and honestly, you often find that people are more willing to change than you expected.
The golden promise of DevSecOps is still achievable, but only if we’re willing to do the harder work of building trust and understanding across the entire organization. This means investing in relationships, communication, and shared context just as much as, or maybe more than, we invest in the latest security tools and automation platforms.
The future of DevSecOps isn’t about perfect tools or flawless processes. It’s about creating environments where developers, operations, and security teams can actually do their best work together, rather than despite each other. The tools and processes will follow naturally when the foundation of trust is solid, but that trust has to come first.