Be the “Sh*t Umbrella”: CTO Lessons on Leadership, Tech Debt, and Exits

Episode notes

What does a CTO actually do when the product is working, customers are paying, and the company needs to scale without breaking? In this episode of SaaS That App: Building B2B Web Applications, Rishi Ramraj, former Chief Technology Officer at Sling, joins Aaron Marchbanks and Justin Edwards to unpack the real job: protecting revenue, supporting people, and building long-term competitive advantage, in that order. What You’ll Learn: How to become a “sh*t umbrella” manager The three-tier CTO priority framework Why measurement before optimization prevents wasted engineering effort How to scale technical teams without proportional headcount growth Why finding “the shittiest company” accelerates management skill development 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.