When a SaaS product is stable, customers are paying, and growth accelerates, the CTO’s job quietly changes. The work is no longer about clever architecture diagrams or heroic late-night coding sessions. In this episode of SaaS That App: Building B2B Web Applications, former Sling CTO Rishi Ramraj joins Aaron Marchbanks and Justin Edwards to explain what the role really becomes: protecting revenue, shielding teams from chaos, and building systems that survive scale.
Rishi describes this shift with a phrase that instantly sticks: the CTO as the “sh*t umbrella.” If something is going wrong, pressure should hit you first, not the engineers doing the work. That mindset shapes everything from leadership style to technical decision-making.
What It Means to Be a “Sh*t Umbrella”
In unhealthy organizations, problems flow downhill until someone gets blamed. Rishi learned early that the fastest way to build trust is to reverse that flow. When incidents happened, he stepped in front of the noise and absorbed it. Blame him. Call him first. Let the team focus on fixing, not defending. Teams that feel safe move faster, communicate earlier, and take smarter risks. Over time, that safety compounds into reliability and velocity, which directly protects the business.
The Three Priorities Every CTO Must Juggle
Rishi frames the CTO role with a simple three-tier priority stack. First, protect the revenue stream. If systems fail, customers leave. Nothing else matters until that risk is under control. Second, support your people. Burned-out teams create hidden fragility that shows up later as outages, attrition, or missed opportunities. Third, create a competitive advantage through scalability, technical debt reduction, and platform improvements.
The power of this framework is the order. Many leaders jump straight to refactors and rewrites. Rishi argues that unless revenue and people are stable, those investments rarely pay off.
Why Measuring Beats Guessing
One of Sling’s biggest scaling wins came from realizing the team had been optimizing the wrong thing. Engineers focused on application-level tweaks because that’s where their experience lived. The real bottleneck, however, was in the database.
Instead of guessing, Rishi pushed for measurement. Upgrade the database. Watch the metrics. See what changes. During a road trip through Central America, he built tooling that allowed major database upgrades with zero downtime. As a side effect, indexes and data structures were repacked, instantly unlocking capacity the team didn’t know they had.
Scaling Output Without Scaling Headcount
When COVID hit, Rishi assumed it would trigger economic instability and inflation. His response was counterintuitive but deliberate: grow the business without growing headcount. That constraint forced better systems, better training, and clearer ownership.
A huge portion of his time shifted to one-on-ones. Not status checks, but coaching sessions. The goal was to help people take on the highest level of responsibility they could safely handle. Junior engineers began submitting performance improvements. Ownership spread downward. The cultural rule became simple: it’s okay to try and fail, but it’s not okay to not try.
Learning Leadership in the Messiest Places
Rishi has an unconventional take on learning management: don’t look for the perfect company. Look for the mess. Real management is learned when priorities clash, communication breaks down, and someone has to step in before things get worse.
In those environments, you quickly figure out how to handle blame, calm situations down, and keep your team moving forward when everything around them feels unstable. It’s uncomfortable, but it accelerates growth. And once you’ve learned to lead in chaos, applying those skills in a healthier organization feels almost easy.
Final Thoughts
Rishi’s perspective reframes what senior technical leadership really means. The job is to create an environment where revenue is protected, people feel safe to perform, and systems quietly support growth. Being a “sh*t umbrella” is often the difference between a company that scales cleanly and one that collapses under its own success.
Growth doesn’t reward heroics. It rewards clarity, resilience, and calm decision-making under pressure. The best CTOs build teams and trust them, systems that fail gracefully, and organizations prepared for exits, downturns, and the next unexpected challenge without losing momentum, focus, or humanity. That discipline is what separates scalable companies from fragile ones.
Rishi’s Background
Rishi Ramraj is the former Chief Technology Officer at Sling, a shift scheduling and workforce management platform used by businesses to keep teams aligned and operations running smoothly. He has spent over two decades in the technology industry, building and leading software systems across various engineering roles. As CTO of Sling, Rishi leads the development of a B2B web application designed to support operational workflows for businesses managing hourly teams.
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