Rebecca Greene, Co-Founder and CTO of Regal.ai, shares her unconventional journey from financial services to leading engineering and product at a fast growing SaaS company. In this episode, she opens up about what it takes to build a product led organization without a computer science background, how she balances technical leadership with business vision, and why hiring great people early changes everything.
Rebecca’s story shows that becoming a CTO isn’t about your degree. It’s about curiosity, adaptability, and learning to lead both people and technology.
Key Takeaways
• The line between product and engineering is intentionally blurred at Regal.ai and it drives faster decisions and better collaboration.
• Nontechnical founders can build successful engineering organizations by hiring strong leaders early and fostering trust through documentation and data.
• Understanding data models is a powerful way to bridge product and engineering.
• Balancing multiple executive roles requires knowing when to go deep and when to step back.
• The modern CTO must think beyond code since hiring, infrastructure choices, and culture are just as critical.
Timestamped Highlights
[00:01:00] How Regal.ai helps B2C brands connect with customers during key buying moments
[00:03:00] From financial services to product management and why Rebecca pivoted into tech
[00:07:00] Learning engineering through hiring, data, and curiosity
[00:09:00] Why “show, don’t tell” became a core part of Regal’s engineering culture
[00:12:00] When to give up titles and hire leaders stronger than you
[00:17:00] What she would change if she could start her career again
[00:19:00] Why nontechnical founders have more tools than ever to build technical companies
One Thing She Said That Stuck
“I’d love to give up every title I have except cofounder because that means I’ve hired people better than me to do the job.”
Pro Tips
For nontechnical founders, learn to speak the language of engineering through data and documentation. You don’t need to code to lead, but you do need to understand how things work and why.
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