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

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

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.

SaaS That App - Building Tech-Enabled Businesses · Delta Systems

February 3, 202639m 35s

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Show 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. As the former CTO of Sling, Rishi leads the development of a B2B web application designed to support operational workflows for businesses managing hourly teams.

This podcast is brought to you by Delta Systems, your one-stop shop for front-end, back-end, and full-stack software development. At Delta, Justin and Aaron share the same philosophy when it comes to clients: they treat people like colleagues, not just customers. Maybe that’s why Delta typically spends years working with the same companies: how many software engineering firms can you say that about? So, if you’ve got a big SaaS project in mind but have no idea where to start, come and get a free scope and estimate from Delta Systems on their website.

Got a burning idea for an episode, or a SaaS question you absolutely must know the answer to? Leave us a voice memo at SaasThatApp

Highlights:
  • [00:00] Introduction
  • [02:18] How Rishi Got Into Tech
  • [06:24] What Good Management Looks Like
  • [09:16] What Early Startups Taught Rishi
  • [14:13] Why Keep Working After You Don’t Have To
  • [19:18] What a CTO Prioritizes
  • [22:48] How COVID Changed the Scaling Strategy
  • [24:25] How to Handle Technical Debt Without Rewriting Everything
  • [28:03] Scaling Without a Big Ops Team
  • [31:55] What 1:1 Are For
  • [33:59] The Exit Story
  • [38:14] Where to Find Rishi

Episode Resources:
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