In my first SaaS leadership roles, I was responsible for both integration and, later, product management. It was a high-stakes environment where the platform, frankly, had its fair share of limitations. However, I quickly discovered what I now consider the hidden gem of that business—a secret sauce that led to our overwhelming success despite the technical hurdles.
It wasn’t the code; it was the people. Specifically, it was that our employees were not constrained by their job descriptions. They were empowered to identify workarounds, collaborate directly with the product team, and—most crucially—they had direct access to developers. We weren’t siloed. It was a mutually beneficial ecosystem where people who were technically degrees apart from our clients got to hear about their problems firsthand. I remember account managers (AMs) and developers sitting in the same meetings, hashing out solutions in real time. That lack of friction was our greatest competitive advantage.
Today, in my role at Overfuel, we are experiencing the same level of great success, for the exact same reasons. Our leadership and development teams are hands-on. We don’t just look at data points; we understand the visceral impact our platform has on the auto dealerships we work with. But I’ve also seen the dark side of this trajectory, and it’s a cautionary tale every SaaS leader needs to hear.
The Slow Creep of the Silo
Years after that first success, I witnessed a transformation that still haunts me. Following a period of massive investment, the professional managers arrived. Middle management settled in, and with them came the walls. They built silos under the guise of efficiency and process.
Almost instantly, we started to see devastating results. The fluid communication that once defined us was replaced by a rigid hierarchy. I became a vocal opponent of this new process and eventually left the organization because I could see the writing on the wall. When you prioritize the sanctity of the department over the resolution for the customer, you are effectively dismantling the engine of your own growth.
Thankfully, my leadership at Overfuel has always been hands-on with each of their startups. We’re not changing.
The Dual Disaster: A Systemic Failure
When an organization chooses to silo its departments, specifically by stripping power away from account management and customer service, it triggers what I call a Dual Disaster. This isn’t just a minor operational hiccup; it is a fundamental breakdown of the business model.
CX Decline
First, customers simply cannot get the resolution they require. When a frontline employee is forced to say, “I’ll have to put in a ticket for that,” with no timeline or internal leverage to back it up, the relationship begins to sour. This leads to a cycle of frustration and conflict.
The account manager, once a hero to the client, is reduced to a messenger for bad news. Ultimately, the trust is broken, and the customer list begins to bleed out.
Knowledge Decline
The second disaster is even more insidious because it’s harder to see on a balance sheet in the short term. The platform stops improving because the knowledge is siloed. In a healthy organization, the boots on the ground are the primary source of innovation. They see the weird use cases, the friction points, and the “good enough” workarounds that should be native features.
When you cut off the developers from these front-line professionals, you are starving your dev team of the context they need to build great software. You end up building features that look good in a boardroom but fail in the field.
Comparing the Cultures
To visualize the difference between these two worlds, we can examine how they operate during a standard operational crisis.
The Connected Culture (Overfuel)The Siloed CultureDev Context: Developers hear the ‘why’ directly from the person speaking to the client.Gatekeeping: AMs must fill out a 12-field form that may be read in two weeks.Problem Solving: Workarounds are celebrated as prototypes for future features.Compliance: Workarounds are discouraged because they break the process.Dev Context: Developers hear the why directly from the person talking to the client.Dev Isolation: Developers receive a Jira ticket with no emotional or business context.Leadership: Hands-on, empathetic, and focused on dealership impact.Leadership: Focused on velocity metrics and department-specific KPIs.Outcome: High retention, rapid innovation, and a motivated workforce.Outcome: Churn, product-market drift, and employee burnout.
The View from the Other Side of the Phone
My experiences have changed the way I interact with the world. Whenever I pick up the phone today and speak to a front-line employee or an account manager at another company, I find myself listening for the silo.
I can tell within thirty seconds when I’m talking to someone who is helpless. I hear it in the hesitation in their voice when I ask for a custom solution, or the practiced, robotic way they recite a policy they clearly don’t agree with. I realize when they have no path to a developer and no voice in the product meeting.
It makes me rethink the relationship entirely. If the person I’m talking to is powerless, then the organization they work for is fundamentally broken. It makes me wonder: If they can’t help me with this simple request, how will they handle a major crisis?
Why Middle Management Fails the Mission
It’s important to understand that middle management rarely sets out to destroy a company. They often believe they are helping. They see a messy communication style and want to clean it up. They see a developer being interrupted by an account manager and want to “protect their time.”
But in SaaS, that interruption is often the most valuable five minutes of the developer’s day. It’s the moment they realize the feature they’re building doesn’t actually solve the dealership’s problem. By protecting the developers, middle management effectively isolates them from reality.
I’ve learned that the moment you start valuing the process of building software more than the impact of the software, you’ve already lost.
Breaking the Barriers: A Path to Reconnection
If you find your organization drifting toward silos, the time to act is now. It requires a radical return to the hidden gem philosophy:
Democratize Access: Give your front-line staff a seat at the table. Not a symbolic seat, but a real one where their feedback directly influences the sprint cycle.
Reward Cross-Pollination: Don’t just measure a developer’s lines of code or story points. Measure their understanding of the client’s business.
Kill the Buffer: If a manager’s primary job is to manage the flow of information between two departments, ask yourself why those departments aren’t just talking to each other directly.
Stay Hands-On: As leaders, we must stay close to the product and the customer. The moment we stop understanding the dealership’s pain, we stop being able to lead the people who solve it.
Success in SaaS isn’t about having the perfect platform from day one. It’s about having a team that is empowered to bridge the gap between what the platform is and what the customer needs it to be.
Takeaway Questions: Identifying Your Organization
If you are unsure where your company stands, use these questions as a litmus test. Be honest—the health of your business depends on it.
To the Front Line: If you discovered a brilliant workaround today that helped a client, would you be praised for your ingenuity or reprimanded for going outside the process?
To the Developers: Can you name the top three frustrations of your current power users, or are you only aware of the priority level of your current tickets?
To the Managers: Do your meetings focus more on who is allowed to talk to whom or on how we can solve this problem?
To Leadership: When was the last time you sat in on a standard support call or an account review without leading the meeting?
To the Organization: Is the distance between a client’s pain point and a developer’s keyboard measured in minutes or in management layers?
To the Customer: Does your customer feel like they are partnering with a team of experts, or like they are shouting into a corporate void?
The answers to these questions will tell you everything you need to know about your company’s future. Don’t wait for the massive investment to build the walls… keep them down, stay hands-on, and empower your employees.
©2026 DK New Media, LLC, All rights reserved | DisclosureOriginally Published on Martech Zone: SaaS Success Lives and Dies in the Gaps Between Siloed Departments